1-Phenylpropan-1-one (1-Phenyl-1-propanone; Propiophenone) [C9H10O] by Asch

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Date

824 reactions in Reaxys

2018-07-03 17h:54m:34s (UTC)

1. Query

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='93-55-0') AND (IDE.INCHI='KRIOVPPHQSLHCZ-UHFFFAOYSA-N') NOT (RX.RXRN=606215))

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O HO

Rx-ID: 280279 View in Reaxys 1/824 Yield 100.0 %

Conditions & References With silica-supported Jones reagent in dichloromethane, Time= 0.00269444h Wiles, Charlotte; Watts, Paul; Haswell, Stephen J.; Tetrahedron Letters; vol. 47; nb. 30; (2006); p. 5261 - 5264 View in Reaxys

100 %

With ruthenium trichloride, iodobenzene, potassium hydrogen persulfate in water, acetonitrile, Time= 0.3h, T= 20 °C Yusubov, Mekhman S.; Zagulyaeva, Aleksandra A.; Zhdankin, Viktor V.; Chemistry - A European Journal; vol. 15; nb. 42; (2009); p. 11091 - 11094 View in Reaxys

100 %

With ruthenium trichloride, iodobenzene, potassium peroxymonosulfate in water, acetonitrile, Time= 0.3h, T= 20 °C , Inert atmosphere Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor V.; Tetrahedron; vol. 66; nb. 31; (2010); p. 5745 - 5752 View in Reaxys

100 %

8.12 : Example 8 Application of this method in the reaction of other alcohols to aldehydes and ketones The typical reaction steps are as follows:1 mmol of the starting alcohol of the reactant column shown in Table 2,OH - Ni3InLDH 14 mg,Mesitylene 5mL were added to the reactor,Into the oxygen,Atmospheric reaction,The reaction was stirred at 60 for a certain period of time.The solid catalyst was removed by filtration,Using gas chromatography internal standard method (chlorobenzene as internal standard) to analyze the content of liquid products,Calculate yield. With oxygen in 1,3,5-trimethyl-benzene, Time= 5h, T= 60 °C , p= 760.051Torr , Solvent, Reagent/catalyst Patent; Changzhou University; Zhou Weiyou; Dai Xuan; He Mingyang; Sun Fuan; Pan Jiugao; (8 pag.); CN107176898; (2017); (A) Chinese View in Reaxys

99 %

With sodium bromate in acetonitrile, Time= 48h, Heating Al-Haq, Nazli; Sullivan, Alice C.; Wilson, John R. H.; Tetrahedron Letters; vol. 44; nb. 4; (2003); p. 769 - 771 View in Reaxys

99 %

With iodine, potassium carbonate in tert-butyl alcohol, Time= 8h, T= 90 °C Mori, Naoshi; Togo, Hideo; Tetrahedron; vol. 61; nb. 24; (2005); p. 5915 - 5925 View in Reaxys

99 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, sodium hypochlorite, silica gel, potassium bromide in dichloromethane, Time= 1h, T= 0 °C , pH= 9.1, Anelli oxidation Fey, Thomas; Fischer, Holger; Bachmann, Stefan; Albert, Klaus; Bolm, Carsten; Journal of Organic Chemistry; vol. 66; nb. 24; (2001); p. 8154 - 8159 View in Reaxys

99 %

With sodium bromide, sodium hydrogencarbonate in dichloromethane, T= 20 °C , Electrochemical reaction Demizu, Yosuke; Shiigi, Hirofumi; Oda, Takahisa; Matsumura, Yoshihiro; Onomura, Osamu; Tetrahedron Letters; vol. 49; nb. 1; (2008); p. 48 - 52 View in Reaxys

99 %

With (η3-cinnamyl)Pd(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)(Cl), para-chlorotoluene, sodium t-butanolate in toluene, Time= 1.5h, T= 25 °C , Inert atmosphere Landers, Brant; Berini, Christophe; Wang, Chao; Navarro, Oscar; Journal of Organic Chemistry; vol. 76; nb. 5; (2011); p. 1390 - 1397 View in Reaxys

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99 %

With oxalyl dichloride, 3-methyl-1-[6-(methanesulfinyl)hexan-1-yl]-1H-imidazolium p-toluenesulfonate, triethylamine in dichloromethane, T= -78 - 20 °C , Swern oxidation Tsuchiya, Daisuke; Moriyama, Katsuhiko; Togo, Hideo; Synlett; nb. 18; (2011); p. 2701 - 2704 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, N-methyl-N-[3-(4'-diacetoxyiodo)phenoxy-1-propyl]pyrrolidinium 4methylbenzenesulfonate in dichloromethane, Time= 4.5h, T= 20 °C Suzuki, Yusuke; Iinuma, Masataka; Moriyama, Katsuhiko; Togo, Hideo; Synlett; vol. 23; nb. 8; (2012); p. 1250 - 1256 View in Reaxys

99 %

4.7. General procedure for the Swern oxidation using ion-supported methyl sulfoxide A-1 or B-1 General procedure: Oxalyl chloride (0.34 mL) was added dropwise to a solution of ion-supported methyl sulfoxide A-1 (C6) (1.60 g, 4.0 mmol) in CH2Cl2 (6 mL) at -70 °C and the mixture was stirred for 30 min at the same temperature. Then, a solution of alcohol (2.0 mmol) in CH2Cl2 (3 mL) was added dropwise at -70 °C and the obtained mixture was stirred for 30 min. Triethylamine (1.66 mL, 12 mmol) was added dropwise at -70 °C and the mixture was stirred for 1 h at the same temperature. The resulting mixture was warmed to -60 °C and stirred for 1.5 h at the same temperature. Then, the mixture was warmed to -50 °C and stirred for 1 h at the same temperature. Finally, the mixture was warmed to room temperature and stirred for 2 h at the same temperature. The reaction mixture was quenched with water (10 mL), neutralized (pH=6-7) with aq 1 M HCl solution, and extracted with diethyl ether (40 mL.x.2). The organic layer was washed with water (10 mL), dried over Na2SO4, and filtered. After removal of the solvent, aldehyde or ketone was obtained. The purity was estimated by 1H NMR measurements. Stage 1: With oxalyl dichloride, 3-methyl-1-[6-(methanesulfinyl)hexan-1-yl]-1H-imidazolium p-toluenesulfonate in dichloromethane, Time= 0.5h, T= -70 °C , Swern oxidation Stage 2: With triethylamine in dichloromethane, Time= 5.5h, T= -70 - 20 °C , Swern oxidation Tsuchiya, Daisuke; Tabata, Masayuki; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 68; nb. 34; (2012); p. 6849 6855 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, N-methyl-N-[3-(4-diacetoxyiodo)phenoxy-1-propyl]pyrrolidinium 4methylbenzenesulfonate in dichloromethane, Time= 4.5h, T= 20 °C , Inert atmosphere Iinuma, Masataka; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 69; nb. 14; (2013); p. 2961 - 2970 View in Reaxys

99 %

IBS-catalysed alcohol oxidation in CTAB micelle; general procedure General procedure: The alcohol (2 mmol) was added to a solution of IBS (0.02 mmol, 0.01 eq), oxone (2.2 mmol, 1.1 equiv.) and 3 wtpercent CTAB solution (5 mL). The mixture was stirred at room temperature. The reaction was monitored by TLC. After completion, the solution was extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was then filtered through a pad of silica gel and evaporated under vacuum to afford the desired product. With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide, Oxone, cetyltrimethylammonim bromide in water, Time= 2h, T= 20 °C , Green chemistry, Reagent/catalyst, Temperature, Time, chemoselective reaction Liu, Yangyang; Wang, Boliang; Journal of Chemical Research; vol. 38; nb. 7; (2014); p. 427 - 431 View in Reaxys

> 99 %

With Oxone, potassium bromide in water, acetonitrile, Time= 1h, T= 20 °C , Reagent/catalyst, Solvent Moriyama, Katsuhiko; Takemura, Misato; Togo, Hideo; Journal of Organic Chemistry; vol. 79; nb. 13; (2014); p. 6094 6104 View in Reaxys

99 %

4 : 4.1.1. The oxidation of secondary alcohols General procedure: A round-bottom flask was charged with alcohol (2 mmol), CuOTf (0.1 mmol, 0.05 equiv) (S)-5-(pyrrolidin-2-yl)-1H-tetrazole (0.1 mmol, 0.05 equiv), TEMPO (0.1 mmol, 0.05 equiv), t-BuOK (2 mmol, 1 equiv) and DMF (5 ml). The reaction mixture was stirred at 25 °C open to air until the completion of the reaction, as monitored by TLC. The mixture was then diluted with CH2Cl2 (20 ml), washed with water, dried over Na2SO4, and evaporated under vacuum to give the crude product, which was purified by column chromatography to give the pure product. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, potassium tert-butylate, copper(I) triflate, 5-[(2S)-pyrrolidine-2-yl]-1Htetrazole in N,N-dimethyl-formamide, Time= 1h, T= 25 °C , Catalytic behavior, Reagent/catalyst, Solvent, Time

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Liu, Yangyang; Xie, Aming; Li, Junjian; Xu, Xiao; Dong, Wei; Wang, Boliang; Tetrahedron; vol. 70; nb. 52; (2014); p. 9791 - 9796 View in Reaxys > 99 %

With tert.-butylnitrite, oxygen, acetic acid in toluene, Time= 2h, T= 50 °C Karimi, Babak; Vahdati, Saleh; Vali, Hojatollah; RSC Advances; vol. 6; nb. 68; (2016); p. 63717 - 63723 View in Reaxys

99 %

With dihydrogen peroxide in neat (no solvent), Time= 1h, T= 70 °C , Green chemistry, chemoselective reaction Darvishi, Kamran; Amani, Kamal; Rezaei, Manuchehr; Applied Organometallic Chemistry; vol. 32; nb. 5; (2018); Art.No: E4323 View in Reaxys

98 %

With TMB*HBr, 3-chloro-benzenecarboperoxoic acid in dichloromethane, 1.) 0 deg C, 10 min, 2.) 23 deg C, 30 min Rychnovsky, Scott D.; Vaidyanathan, Rajappa; Journal of Organic Chemistry; vol. 64; nb. 1; (1999); p. 310 - 312 View in Reaxys

98 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, ammonium cerium(IV) nitrate, oxygen in acetonitrile, Time= 1h, T= 82 °C Kim, Sung Soo; Jung, Hyun Chul; Synthesis; nb. 14; (2003); p. 2135 - 2137 View in Reaxys

98 %

With dinitrogen tetroxide impregnated on activated charcoal in dichloromethane, Time= 3.5h, T= 20 °C Iranpoor, Nasser; Firouzabadi, Habib; Pourali, Ali Reza; Synthetic Communications; vol. 35; nb. 11; (2005); p. 1527 - 1533 View in Reaxys

98 %

With o-xylylenebis(triphenylphosphonium) peroxymonosulfate, aluminium trichloride, Time= 0.0833333h Tajbakhsh, Mahmoud; Lakouraj, Moslem-Mansor; Yadoolahzadeh, Khadijeh; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 180; nb. 11; (2005); p. 2431 - 2437 View in Reaxys

98 %

With pyridine, air, Pd(II)-hydrotalcite in toluene, Time= 10h, T= 65 °C , p= 760.051Torr Kakiuchi; Maeda; Nishimura; Uemura; Journal of Organic Chemistry; vol. 66; nb. 20; (2001); p. 6620 - 6625 View in Reaxys

98 %

With hydrogenchloride, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium nitrite in dichloromethane, water, Time= 12h, T= 20 °C , p= 760.051Torr , in air Wang, Xinliang; Liu, Renhua; Jin, Yu; Liang, Xinmiao; Chemistry - A European Journal; vol. 14; nb. 9; (2008); p. 2679 2685 View in Reaxys

98 %

With bis(1,5-cyclooctadiene)nickel (0), potassium tert-butylate, 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride in toluene, Time= 12h, T= 25 °C , Inert atmosphere Berini, Christophe; Navarro, Oscar; Chemical Communications; vol. 48; nb. 10; (2012); p. 1538 - 1540 View in Reaxys

98 %

With C53H46ClN3P2Ru, potassium tert-butylate, acetone, Time= 0.166667h, T= 56 °C , p= 750.075Torr , Oppenauer Oxidation Du, Wangming; Wang, Liandi; Wu, Ping; Yu, Zhengkun; Chemistry - A European Journal; vol. 18; nb. 37; (2012); p. 11550 - 11554 View in Reaxys

98 %

A typical procedure for the catalytic oxidation of alcohols General procedure: The catalyst solutionwas prepared by dissolving complex 3(36.1 mg,0.05mmol) in methanol (5.0 mL).Under a nitrogen atmosphere, the mixture of an alcohol substrate (2.0 mmol) and1.0 mL of the catalyst solution (0.01mmol) in 20mL acetone was stirred at 56 Cfor 10 minutes. tBuOK(22.4mg, 0.2 mmol)was then added to initiate the reaction.At the stated time, 0.1 mL of the reaction mixture was sampled and immediately diluted with 0.5 mL acetone pre-cooled-to-0 C for GC or NMR analysis. After the reaction was complete, the reaction mixture was condensed under reduced pressure and subject to purification

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by flash silica gel column chromatography to afford the corresponding ketone product, which was identified by comparison with the authentic sample through NMR and GC analysis. With [(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine)RuCl2(PPh3)], potassium tert-butylate, acetone in methanol, Time= 0.25h, T= 56 °C , p= 750.075Torr , Inert atmosphere, Oppenauer Oxidation, Catalytic behavior Wang, Qingfu; Du, Wangming; Liu, Tingting; Chai, Huining; Yu, Zhengkun; Tetrahedron Letters; vol. 55; nb. 9; (2014); p. 1585 - 1588 View in Reaxys 98 %

With potassium hexafluorophosphate, tert.-butylnitrite, 9-azabicyclo<3.3.1>nonane-N-oxyl, oxygen in water, Time= 2h, T= 60 °C , p= 2250.23Torr , Autoclave, Green chemistry Ma, Jiaqi; Hong, Chao; Wan, Yan; Li, Meichao; Hu, Xinquan; Mo, Weimin; Hu, Baoxiang; Sun, Nan; Jin, Liqun; Shen, Zhenlu; Tetrahedron Letters; vol. 58; nb. 7; (2017); p. 652 - 657 View in Reaxys

97 %

With barium permanganate, Time= 4h, T= 90 °C , Oxidation Firouzabadi, Habib; Karimi, Babak; Abbassi, Mohammad; Journal of Chemical Research - Part S; nb. 3; (1999); p. 236 237 View in Reaxys

97 %

With manganese(III) Schiff-base, dihydrogen peroxide, Time= 5h, T= 20 °C Mardani, Hamid R.; Golchoubian, Hamid; Tetrahedron Letters; vol. 47; nb. 14; (2006); p. 2349 - 2352 View in Reaxys

97 %

With NTPPPODS in acetonitrile, Time= 0.0666667h, Reflux Lakouraj, Moslem Mansour; Tajbakhsh, Mahmood; Ramzanian-Lehmali, Farhad; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 183; nb. 6; (2008); p. 1388 - 1395 View in Reaxys

97 %

With (IPr)Ni(dmfu)2, potassium tert-butylate in 2,4-dichlorotoluene, Time= 2.5h, T= 40 °C , Inert atmosphere Berini, Christophe; Winkelmann, Ole H.; Otten, Jennifer; Vicic, David A.; Navarro, Oscar; Chemistry - A European Journal; vol. 16; nb. 23; (2010); p. 6857 - 6860 View in Reaxys

97 %

With oxygen, isobutyraldehyde in acetonitrile, Time= 2.5h, T= 50 °C , p= 760.051Torr Rana, Bharat S.; Jain, Suman L.; Singh, Bhawan; Bhaumik, Asim; Sain, Bir; Sinha, Anil K.; Dalton Transactions; vol. 39; nb. 33; (2010); p. 7760 - 7767 View in Reaxys

97 %

With (IPr)Ni(Cp)Cl, sodium t-butanolate in 2,4-dichlorotoluene, Time= 0.5h, T= 110 °C , Microwave irradiation Landers, Brant; Navarro, Oscar; Inorganica Chimica Acta; vol. 380; nb. 1; (2012); p. 350 - 353 View in Reaxys

97 %

With (R,R)-1,2-di(1-naphthyl)-1,2-ethanediamine, tert.-butylhydroperoxide, potassium carbonate in water, Time= 9h, T= 95 °C , Temperature Al-Hunaiti, Afnan; Räisänen, Minna; Pihko, Petri; Leskelä, Markku; Repo, Timo; European Journal of Organic Chemistry; vol. 2014; nb. 28; (2014); p. 6141 - 6144 View in Reaxys

97%

With doubly supported catalyst Pd(at)MIL-88B-NH2(at)nano-SiO2, air in para-xylene, Time= 15h, T= 150 °C Pascanu, Vlad; Bermejo Gómez, Antonio; Ayats, Carles; Platero-Prats, Ana Eva; Carson, Fabian; Su, Jie; Yao, Qingxia; Pericàs, Miquel À.; Zou, Xiaodong; Martín-Matute, Belén; ACS Catalysis; vol. 5; nb. 2; (2015); p. 472 - 479 View in Reaxys

97 %

With hydrogenchloride, tert.-butylnitrite, TEMPOL, oxygen, chloranil in neat (no solvent), Time= 12h, T= 20 °C , p= 760.051Torr , Green chemistry

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Dong, Yanli; Zhao, Xiaomei; Liu, Renhua; Chinese Journal of Chemistry; vol. 33; nb. 9; (2015); p. 1019 - 1023 View in Reaxys 97 %

General procedure to prepare carbonyl compounds 2a–v. General procedure: 2,2,6,6-Tetramethylpiperidine 1-oxyl (TEMPO, 9.4 mg,0.06 mmol, 3 mol percent), 2,2η-bipyridyl (9,4 mg, 0.06 mmol,3 mol percent), [Cu(CN)4]OTf (22.6 mg, 0.06 mmol, 3 mol percent) and1-methylimidazole (NMI, 11.5 mg, 11.2 μL, 0.14 mmol,7 mol percent) were placed in a zirconia-milling beaker (45 mL)equipped with four balls (two balls × 5 mm , two balls ×12 mm ) of the same material. The jar was sealed and ballmilled for 1 min. Then, benzyl alcohol (216.3 mg, 207 μL,2.0 mmol), NaCl (1.0 g) together with other two zirconia balls(12 mm ) were added and the reaction mixture was subjectedto grinding for further 10 minutes overall (two cycles of5 minutes each). The first milling cycle was followed by a breakof 2 min leaving in the meantime the uncovered jar in open air.The progress of the reaction was monitored by TLC analysis(heptane/AcOEt 9:1 v/v) and GC–MS analysis on an aliquot ofthe crude. Upon completion of the ball milling process, the jarwas opened, the milling balls were removed and the resultingcrude product (adsorbed on NaCl) was then easily transferredinto a separating funnel filled with an aqueous 10percent citric acidsolution (20 mL). The aqueous phase was extracted withcyclopentyl methyl ether (or alternatively with AcOEt)(3 × 15 mL). The combined organic fractions were washed withH2O (25 mL) and brine (25 mL), then dried over Na2SO4, andconcentrated in vacuo to give benzaldehyde in high yield (195 mg, 92percent) and good purity (>93percent by GC analysis). Alternatively, after completion of the reaction, the resulting crudeproduct (adsorbed on NaCl) can be also easily purified by ashort column chromatography on silica gel using heptane/ethylacetate (9:1 v/v) as the eluents to afford pure aldehyde 2b inhigh yield (202 mg, 95percent) as a colourless liquid. With 1-methyl-1H-imidazole, [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, sodium chloride in neat (no solvent), Milling, Green chemistry Porcheddu, Andrea; Colacino, Evelina; Cravotto, Giancarlo; Delogu, Francesco; De Luca, Lidia; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 2049 - 2055 View in Reaxys

97 %

With C55H49N4OP2Ru in toluene, p= 750.075Torr , Inert atmosphere, Schlenk technique, Reflux, Green chemistry Wang, Qingfu; Chai, Huining; Yu, Zhengkun; Organometallics; vol. 37; nb. 4; (2018); p. 584 - 591 View in Reaxys

96 %

With diisopropoxyaluminium trifluoroacetate, 4-nitrobenzaldehdye in benzene, Time= 0.333333h, Ambient temperature Akamanchi, Krishnacharya G.; Chaudhari, Bapu A.; Tetrahedron Letters; vol. 38; nb. 39; (1997); p. 6925 - 6928 View in Reaxys

96 %

With bromine in dichloromethane, Time= 1h, T= 20 °C Lakouraj, Moslem Mansour; Tajbakhsh, Mahmood; Mokhtary, Masoud; Journal of Chemical Research; nb. 8; (2005); p. 481 - 483 View in Reaxys

96 %

With {-N(+)(CH3)2CH2CH2N(+)[(CH3)2](CH2)4-}n*S2O8 (2-) in water, Time= 0.25h, Heating Tajbakhsh, Mahmood; Lakouraj, Moslem Mansour; Ramzanian-Lehmali, Farhad; Synlett; nb. 11; (2006); p. 1724 - 1728 View in Reaxys

96 %

Typical procedure of the SiO2-supported iodoarene-RuCl3 catalyzed oxidation of alcohols and aromatic hydrocarbons: General procedure: Oxone (0.374 g; 0.6 mmol) was added to a mixture of 1-phenylethanol (25 mg, 0.2 mmol), catalyst 5 or 6 (15 mg) in acetonitrile (1 mL) and water (1 mL) in one portion under stirring at room temperature. The reaction was monitored by TLC by the disappearance of 1-phenylethanol. Then ethyl acetate (3 mL) and water (5 mL) were added and the mixture was stirred for 5 min. The catalyst was filtered, washed with water (2x1 mL), ethyl acetate (2 x 1 mL) and collected, thereby directly being used for next run under the same conditions. The organic solution was separated and the aqueous phase was extracted with ethyl acetate (2 x 5 mL). The organic phases were combined, washed with brine (5 mL), and dried over anhydrous Na2SO4. Removal of the solvent under vacuum afforded acetophenone. The oxidation of the other alcohols and hydrocarbons was performed using a similar procedure. In all cases, conversions were measured by GC-MS with a prior column calibration using authentic samples of reactants and products. The reaction products were isolated by removal of the solid resin followed by aqueous work-up of organic solution; products 10 and 14 were identified by comparison of the retention times and MS data with those obtained for authentic samples or by 1H NMR. Representative spectra are provided below. In the oxidation protocol, the bifunctional SiO2-supported iodoarene-RuCl3 catalysts 5 and 6 were easily separated by filtration and directly reused without noticeable loss of their activity. With Oxone in water, acetonitrile, Time= 1h, T= 20 °C

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Zeng, Xiao-Mei; Chen, Jiang-Min; Middleton, Kyle; Zhdankin, Viktor V.; Tetrahedron Letters; vol. 52; nb. 43; (2011); p. 5652 - 5655 View in Reaxys 96 %

2.3. Procedure for oxidation of benzylic alcohols by [CuNi(-OAc)(-OH)(-OH2)(bpy)2](ClO4)2 To a mixture of benzyl alcohol (0.5 mL, 4.64 mmol) and 15percent aqueous hydrogen peroxide(1.1 mL, 4.85 mmol), the catalyst [CuNi(-OAc)(-OH)(-OH2)(bpy)2](BF4)2 (8 mg, 0.01 mmol)was added and stirred at 70 °C for 5 h. The organic and aqueous phase were separated by aseparating funnel and then puried by column chromatography to aord benzaldehyde.The identity of the benzaldehyde was ascertained by comparison with authentic sampleusing IR, 1H NMR, and 13C NMR. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [CuNi(-OAc)(μ-OH)(μ-OH2)(bpy)2](ClO4)2, dihydrogen peroxide in water, Time= 3h, T= 70 °C Lal, Ram A.; Kumar, Arvind; Syiemlieh, Ibanphylla; Kurbah, Sunshine D.; Journal of Coordination Chemistry; vol. 70; nb. 15; (2017); p. 2722 - 2735 View in Reaxys

95 %

With 2,2'-bipyridylchromium peroxide in benzene, Time= 0.8h, Heating Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Tetrahedron; vol. 42; nb. 2; (1986); p. 719 - 726 View in Reaxys

95 %

With cethyltrimethylammonium permanganate in dichloromethane, Time= 1.5h, T= 28 - 30 °C Rathore, R.; Bhushan, Vidya; Chandrasekaran, S.; Chemistry Letters; (1984); p. 2131 - 2134 View in Reaxys

95 %

With 2,2'-bipyridylchromium peroxide in benzene, Time= 0.8h, Heating, effect of various chromium(VI) based oxidants, Product distribution Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Tetrahedron; vol. 42; nb. 2; (1986); p. 719 - 726 View in Reaxys

95 %

With pyridine, oxygen, Pd(II)-hydrotalcite in toluene, Time= 3h, T= 80 °C Uemura; Kakiuchi; Nishimura; Inoue; Bulletin of the Chemical Society of Japan; vol. 74; nb. 1; (2001); p. 165 - 172 View in Reaxys

95 %

With potassium permanganate, zirconium(IV) oxychloride in diethyl ether, Time= 4.5h, T= 20 °C Firouzabadi; Fakoorpour; Hazarkhani; Synthetic Communications; vol. 31; nb. 24; (2001); p. 3859 - 3862 View in Reaxys

95 %

With N-hydroxyphthalimide, ammonium cerium(IV) nitrate, oxygen in acetonitrile, Time= 1.3h, Heating Kim, Sung Soo; Rajagopal, Gurusamy; Synthetic Communications; vol. 34; nb. 12; (2004); p. 2237 - 2243 View in Reaxys

95 %

With tert.-butylhydroperoxide, iron(III) chloride, thymidyl acetic acid in decane, Time= 3h, T= 80 °C Al-Hunaiti, Afnan; Niemi, Teemu; Sibaouih, Ahlam; Pihko, Petri; Leskelae, Markku; Repo, Timo; Chemical Communications; vol. 46; nb. 48; (2010); p. 9250 - 9252 View in Reaxys

95 %

With oxygen, potassium carbonate in toluene, Time= 21h, T= 100 °C Zhang, Guofu; Wang, Yong; Wen, Xin; Ding, Chengrong; Li, Ying; Chemical Communications; vol. 48; nb. 24; (2012); p. 2979 - 2981 View in Reaxys

95 %

General procedure: Alcohol (1 mmol) and NaOCl (ca. 13percent, 5 mL) were dissolved in HFIP (1 mL) and was stirred at 25-30 °C in a vial for 3 h. After completion of the reaction as indicated by TLC, the HFIP was separated by distillation and then the mixture was extracted with diethyl ether (3 x 25 mL). The combined organic layers were washed with H2O and dried over MgSO4. The solvent was removed under vacuum, and the residue was purified bychromatography. All the products were characterized by comparison of their physical and spectral data with those of authentic samples. With sodium hypochlorite in 1,1,1,3',3',3'-hexafluoro-propanol, Time= 3h, T= 25 - 30 °C , chemoselective reaction

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Khaksar, Samad; Talesh, Saeed Mohammadzadeh; Journal of Fluorine Chemistry; vol. 140; (2012); p. 95 - 98 View in Reaxys 95 %

With [Fe(1,10-phenanthroline)2Cl2]NO3, dihydrogen peroxide in aq. buffer, Time= 0.5h, T= 55 °C , pH= 1, chemoselective reaction Biswas, Bhaskar; Kole, Niranjan; Al-Hunaiti, Afnan; Raeisaenen, Minna T.; Ansalone, Simone; Leskelae, Markku; Repo, Timo; Chen, Yen-Tung; Tsai, Hui-Lien; Naik, Anil D.; Railliet, Antoine P.; Garcia, Yann; Ghosh, Rajarshi; European Journal of Inorganic Chemistry; nb. 28; (2012); p. 4479 - 4485,7 View in Reaxys

95 %

With dihydrogen peroxide in water, Time= 1.08333h, T= 20 °C Eshtiagh-Hosseini, Hossein; Tabari, Taymaz; Eshghi, Hossein; Asian Journal of Chemistry; vol. 25; nb. 6; (2013); p. 3307 3312 View in Reaxys

95 %

With potassium dichromate, wet-SiO2 (60 %), H2SO4-nano silica, acetic anhydride in neat (no solvent), Time= 0.0333333h, T= 20 °C Saffar-Teluri, Ali; Research on Chemical Intermediates; vol. 39; nb. 7; (2013); p. 3337 - 3343 View in Reaxys

95 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in neat (no solvent), Time= 0.75h, T= 20 °C , Milling Achar, Tapas Kumar; Maiti, Saikat; Mal, Prasenjit; RSC Advances; vol. 4; nb. 25; (2014); p. 12834 - 12839 View in Reaxys

95 %

With dihydrogen peroxide in toluene, Time= 3h, T= 70 °C , Reagent/catalyst Atashin, Hassan; Malakooti, Reihaneh; Journal of the Chinese Chemical Society; vol. 61; nb. 9; (2014); p. 1039 - 1044 View in Reaxys

95.6 %

With tert.-butylhydroperoxide, [C6H5CH2N(CH3)2H]2[Ru(2,6-pyridinedicarboxylate)Cl3] in water, Time= 5h, T= 40 °C , Catalytic behavior Zhang, Yuecheng; Zhao, Liyuan; Zhang, Hongyu; Huang, Rong; Zhao, Jiquan; Applied Organometallic Chemistry; vol. 31; nb. 9; (2017); Art.No: E3709 View in Reaxys

94 %

With caesium fluoroxysulphate in acetonitrile, Time= 1h, Ambient temperature Stavber, Stojan; Planinsek, Zdenka; Kosir, Iztok; Zupan, Marko; Journal of Fluorine Chemistry; vol. 59; nb. 3; (1992); p. 409 - 412 View in Reaxys

94 %

With pyridine, oxygen, palladium diacetate in toluene, Time= 2h, T= 80 °C Nishimura, Takahiro; Onoue, Tomoaki; Ohe, Kouichi; Uemura, Sakae; Tetrahedron Letters; vol. 39; nb. 33; (1998); p. 6011 - 6014 View in Reaxys

94 %

With pyridine, oxygen, palladium diacetate in toluene, Time= 2h, T= 80 °C , Oxidation Nishimura, Takahiro; Onoue, Tomoaki; Ohe, Kouichi; Uemura, Sakae; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6750 - 6755 View in Reaxys

94 %

With poly[4-(diacetoxyiodo)styrene], 2,2,6,6-tetramethyl-piperidine-N-oxyl in acetone, Time= 6h, T= 20 °C Sakuratani, Kenji; Togo, Hideo; Synthesis; nb. 1; (2003); p. 21 - 23 View in Reaxys

94 %

With phosphotungstic acid, ferric nitrate, Time= 0.166667h, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Amani, Kamal; Synthesis; nb. 3; (2003); p. 408 - 412 View in Reaxys

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94 %

With oxygen in water, Time= 14.5h, T= 80 °C , pH= 5, Green chemistry Nabid, Mohammad Reza; Bide, Yasamin; Aghaghafari, Elham; Rezaei, Seyed Jamal Tabatabaei; Catalysis Letters; vol. 144; nb. 2; (2014); p. 355 - 363 View in Reaxys

94 %

Catalytic Studies General procedure: In a typical run, a 25 mL flask was charged with catalyst (100 mg), acetonitrile (5 mL), alcohol (1 mmol), and H2O2 (3 mmol). This mixture was heated in an oil bath at 70°C and the progress of the reaction was monitored by TLC. At the end of the reaction, the catalyst was simply collected using a magnetic bar and the reaction mixture was then transferred out of the flask. The decanted solution was purified on a silica-gel plate or a silica-gel column to obtain the pure product. The structures of the products were established on the basis of their spectral analysis (IR, 1H NMR). With dihydrogen peroxide in acetonitrile, Time= 1.5h, T= 70 °C , chemoselective reaction Afshari, Mozhgan; Gorjizadeh, Maryam; Nazari, Simin; Naseh, Mohammad; Oriental Journal of Chemistry; vol. 29; nb. 4; (2013); p. 1523 - 1530 View in Reaxys

94 %

With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate, oxygen, sodium acetate, nickel dibromide, Time= 48h, T= 120 °C , p= 760.051Torr Urgoitia; Sanmartin; Herrero; Domínguez; Chemical Communications; vol. 51; nb. 23; (2015); p. 4799 - 4802 View in Reaxys

93 %

With 2,6-dimethylpyridine, N-Bromosuccinimide, 1-butyl-3-methylimidazolium Tetrafluoroborate, Time= 1h, T= 40 °C Lee, Jong Chan; Lee, Ji Young; Lee, Jang Mi; Synthetic Communications; vol. 35; nb. 14; (2005); p. 1911 - 1914 View in Reaxys

93 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, Oxone, tetrabutylammomium bromide in toluene, Time= 12h, T= 20 °C , Oxidation Bolm, Carsten; Magnus, Angelika S.; Hildebrand, Jens P.; Organic Letters; vol. 2; nb. 8; (2000); p. 1173 - 1175 View in Reaxys

93 %

With bis(1,5-cyclooctadiene)nickel(0), potassium tert-butylate, 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride in 1,4-dioxane, chlorobenzene, Time= 24h, T= 60 °C Berini, Christophe; Brayton, Daniel F.; Mocka, Corey; Navarro, Oscar; Organic Letters; vol. 11; nb. 18; (2009); p. 4244 4247 View in Reaxys

93 %

General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)2 (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH3CN/H2O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper diacetate in water, acetonitrile, Time= 5h, T= 20 °C , Green chemistry Jiang, Jian-An; Du, Jia-Lei; Wang, Zhan-Guo; Zhang, Zhong-Nan; Xu, Xi; Zheng, Gan-Lin; Ji, Ya-Fei; Tetrahedron Letters; vol. 55; nb. 10; (2014); p. 1677 - 1681 View in Reaxys

93 %

With tert.-butylhydroperoxide, N,N'-(ethylene)bis(4-[2-(ethylthio)ethoxy]salicylideneimine), manganese(II) acetate, trifluoroacetic acid in acetonitrile, Time= 8h, T= 80 °C , p= 15001.5Torr , Mechanism, chemoselective reaction Raeisaenen, Minna T.; Al-Hunaiti, Afnan; Atosuo, Elisa; Kemell, Marianna; Leskelae, Markku; Repo, Timo; Catalysis Science and Technology; vol. 4; nb. 8; (2014); p. 2564 - 2573 View in Reaxys

93.7 %

Catalytic oxidation of alcohols

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General procedure: In a typical process, into a 5-ml two-necked round-bottomflask equipped with a magnetic stirrer were addedRu(pbbp)(pydic) (0.002 mmol) and alcohol (2 mmol)successively at room temperature. The mixture washeated to 60 C under stirring, and then TBHP (70percentaqueous solution) was slowly dropped in 0.5 h. Thereaction was monitored by GC equipped with a SE 54column (30 m 9 0.5 lm). After reaction, the product waspurified by column chromatography over silica gel (eluent:n-hexane/ethyl acetate) and characterized by 1HNMR. With tert.-butylhydroperoxide, Time= 16h, T= 60 °C , Time Zhang, Yuecheng; Chu, Ruosi; Zhang, Hongyu; Zhao, Jiquan; Transition Metal Chemistry; vol. 42; nb. 2; (2017); p. 105 116 View in Reaxys 93 %

With dihydrogen peroxide in water, Time= 2h, T= 60 °C Soleimani, Ebrahim; Yaesoobi, Nadieh; Ghasempour, Hamid Reza; Applied Organometallic Chemistry; vol. 32; nb. 2; (2018); Art.No: E4006 View in Reaxys

92 %

With iodosylbenzene, N,N'-bis(3,5-dichlorosalicylidene)-1,2-ethylenediamino-MnCl in acetonitrile, Time= 1h, T= 20 °C Kim, Sung Soo; Borisova, Galina; Synthetic Communications; vol. 33; nb. 22; (2003); p. 3961 - 3967 View in Reaxys

92 %

With dihydrogen peroxide, poly(N-i-propylacrylamide)-phototungstic acid-based catalyst in water, Time= 2h, T= 90 °C Hamamoto, Hiromi; Suzuki, Yachiyo; Yamada, Yoichi M. A.; Tabata, Hidetsugu; Takahashi, Hideyo; Ikegami, Shiro; Angewandte Chemie - International Edition; vol. 44; nb. 29; (2005); p. 4536 - 4538 View in Reaxys

92 %

With Cp(*)Ir(η1-2-hydroxypyridine)Cl2 in toluene, Time= 20h, Heating Fujita, Ken-Ichi; Tanino, Nobuhide; Yamaguchi, Ryohei; Organic Letters; vol. 9; nb. 1; (2007); p. 109 - 111 View in Reaxys

92 %

With sodium azide, (Dichloroiodo)benzene in acetonitrile, Time= 1h, T= 0 °C Li, Xiao-Qiang; Wang, Wei-Kun; Zhang, Chi; Advanced Synthesis and Catalysis; vol. 351; nb. 14-15; (2009); p. 2342 - 2350 View in Reaxys

92 %

With potassium bromide in water, acetonitrile, Time= 3h, T= 20 °C Chen, Jiang-Min; Zeng, Xiao-Mei; Zhdankin, Viktor V.; Synlett; nb. 18; (2010); p. 2771 - 2774 View in Reaxys

92 %

With oxygen in toluene, Time= 4h, T= 79.84 °C Kantam, M. Lakshmi; Reddy, R. Sudarshan; Pal, Ujjwal; Sudhakar; Venugopal; Ratnam, K. Jeeva; Figueras; Chintareddy, Venkat Reddy; Nishina, Yuta; Journal of Molecular Catalysis A: Chemical; vol. 359; (2012); p. 1 - 7 View in Reaxys

92 %

With potassium hydroxide in o-xylene, Time= 0.666667h, T= 20 °C Shaabani, Ahmad; Keshipour, Sajjad; Hamidzad, Mona; Seyyedhamzeh, Mozhdeh; Journal of Chemical Sciences; vol. 126; nb. 1; (2014); p. 111 - 115 View in Reaxys

92 %

Catalytic studies General procedure: In a Pyrex flask equipped with a magnet bar, a solution of the alcohol (5 mmol) in acetonitrile (10 mL) was prepared. To this solution PTA/Si-imid Si-MNPs (50 mg) was added and purged with O2 and joined through an inlet tube to a balloon filled with O2 before irradiation.The suspension was vigorously stirred and irradiated with a high pressure 400 W mercury lamp using a cut-off Pyrex filter at room temperature. The progress of the reaction was monitored by TLC. At the end of the reaction the organic layer was simply decanted by means of an external magnet. The decanted solution was purified on a silica-gel plate or a silica-gel column to obtain the pure product. The identities of the products were confirmed by FT-IR and 1H NMR spectral data. With oxygen in acetonitrile, Time= 1h, T= 20 °C , Irradiation, Green chemistry, chemoselective reaction

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Afshari, Mozhgan; Gorjizadeh, Maryam; Afshar, Ghazal; Oriental Journal of Chemistry; vol. 29; nb. 4; (2013); p. 1675 1681 View in Reaxys 92 %

2.4 Typical procedure for the oxidation of benzylalcohol General procedure: Benzylalcohol (0.1 g, 1.0 mmol) was added to a two-necked flask equipped with a gas bubbling tube containing colloidal of Co(II)-EDANC (0.2 g) and KOH (0.5 mmol) in o-xylene (5mL). Air was bubbled at arate of 5mL/min into the reaction mixture and the progress of the reaction was followed by thin-layer chromatography (TLC). Upon completion, Co(II)-EDANC was separated by filtration and washed with CH3CN (2 × 5mL). The filtrate solvent was evaporated under vacuum and benzylalcohol was purified with column chromatography with n-hexane:ethylacetate (2:1) in 95percent yield. With potassium hydroxide in o-xylene, Time= 0.666667h, T= 20 °C Shaabani, Ahmad; Keshipour, Sajjad; Hamidzad, Mona; Seyyedhamzeh, Mozhdeh; Journal of Chemical Sciences; vol. 126; nb. 1; (2014); p. 111 - 115 View in Reaxys

91 %

With ruthenium(IV) oxide, sodium dihydrogenphosphate, sodium chloride in tetrachloromethane, water, electrooxidation Torii, Sigeru; Inokuchi, Tsutomu; Sugiura, Toyoyuki; Journal of Organic Chemistry; vol. 51; nb. 2; (1986); p. 155 - 161 View in Reaxys

91 %

With caesium fluoroxysulphate in acetonitrile, Time= 1h, T= 30 - 35 °C Stavber, Stojan; Kosir, Iztok; Zupan, Marko; Journal of Organic Chemistry; vol. 62; nb. 15; (1997); p. 4916 - 4920 View in Reaxys

91 %

With tetrabutylammomium bromide, palladium dichloride, Time= 72h, T= 120 °C Ganchegui, Benjamin; Bouquillon, Sandrine; Henin, Francoise; Muzart, Jacques; Tetrahedron Letters; vol. 43; nb. 37; (2002); p. 6641 - 6644 View in Reaxys

91.5 %

With water, [bis(trifluoroacetoxy)iodo]perfluorooctane, potassium bromide, Time= 0.5h, T= 20 °C Tesevic, Verona; Gladysz; Journal of Organic Chemistry; vol. 71; nb. 19; (2006); p. 7433 - 7440 View in Reaxys

91 %

With tert.-butylhydroperoxide, 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, copper acetylacetonate, Time= 5h, T= 20 °C Liu, Chong; Han, Jinyu; Wang, Juan; Synlett; nb. 4; (2007); p. 643 - 645 View in Reaxys

91 %

With 1,3,5,7-tetrakis-(4-(diacetoxyiodo)phenyl)adamantane, tetraethylammonium bromide in water, Time= 5h, T= 20 °C Takenaga, Naoko; Goto, Akihiro; Yoshimura, Misaki; Fujioka, Hiromichi; Dohi, Toshifumi; Kita, Yasuyuki; Tetrahedron Letters; vol. 50; nb. 26; (2009); p. 3227 - 3229 View in Reaxys

91 %

With sodium perborate tetrahydrate, sulfuric acid, potassium bromide in water, T= 80 °C Han, Mikyoung; Jeong, Ku Sun; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 33; nb. 7; (2012); p. 2405 2406 View in Reaxys

91 %

General Procedure. General procedure: To a stirred solution of a benzylic alcohol (1.0 mmol) in 1 mL [bmim]BF4 was added 65percent nitric acid (0.5 mmol) and copper(II) bromide (0.5 mmol). The reaction mixture was stirred in the air at 60 °C for 4 h and the reaction monitored by TLC for the complete consumption of the benzylic alcohol. The solution was cooled to room temperature and the product is extracted into ethyl acetate (2 20 mL), washed with water and dried over MgSO4. After removal of the solvent under reduced pressure, the crude product was purified by flash chromatography (ethyl acetate/n-hexane = 1:5, v/v) to yield the desired carbonyl compound. With nitric acid, copper(ll) bromide, Time= 4h, T= 60 °C , Ionic liquid, Reagent/catalyst, Solvent

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Lim, Chae Mi; Ha, Su Jeong; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 33; nb. 12; (2012); p. 4258 4260 View in Reaxys 91 %

With tetrabutylammomium bromide, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water, Time= 1h, T= 20 °C , Green chemistry Liu, Yangyang; Xie, Aming; Cao, Meiping; Feng, Liandong; Wang, Boliang; Asian Journal of Chemistry; vol. 27; nb. 2; (2015); p. 587 - 590 View in Reaxys

91 %

With C14H14N6O2, oxygen, sodium acetate, palladium diacetate, Time= 48h, T= 120 °C , p= 760.051Torr Urgoitia, Garazi; Maiztegi, Ainhoa; Sanmartin, Raul; Herrero, María Teresa; Domínguez, Esther; RSC Advances; vol. 5; nb. 125; (2015); p. 103210 - 103217 View in Reaxys

90 %

With alumina supported chromium(VI) oxide in hexane, Time= 24h, Ambient temperature Hirano, Masao; Kuroda, Hisanori; Morimoto, Takashi; Bulletin of the Chemical Society of Japan; vol. 63; nb. 8; (1990); p. 2433 - 2434 View in Reaxys

90 %

With tert.-butylhydroperoxide, chromium(VI) oxide in dichloromethane, Time= 3h, Ambient temperature Muzart, Jacques; Tetrahedron Letters; vol. 28; nb. 19; (1987); p. 2133 - 2134 View in Reaxys

90 %

With dinitratocerium (IV) chromate in benzene, Time= 1h, Heating Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Synthetic Communications; vol. 14; nb. 10; (1984); p. 973 - 982 View in Reaxys

90 %

With 2,6-dicarboxypyridinium fluorochromate, Time= 0.166667h, T= 20 °C Tajbakhsh; Hosseinzadeh; Sadatshahabi; Synthetic Communications; vol. 35; nb. 11; (2005); p. 1547 - 1554 View in Reaxys

90 %

With oxygen, phosphotungstic acid, silica gel in acetonitrile, Time= 1.5h, T= 20 °C , UV-irradiation Farhadi, Saeid; Afshari, Mozhgan; Maleki, Mansoureh; Babazadeh, Zaynab; Tetrahedron Letters; vol. 46; nb. 49; (2005); p. 8483 - 8486 View in Reaxys

90 %

With trichloroisocyanuric acid in water, Time= 1h, T= 20 °C , Ionic liquid Lee, Jong Chan; Kim, Jimi; Lee, Seung Bae; Chang, Soon-Uk; Jeong, Yeon Jin; Synthetic Communications; vol. 41; nb. 13; (2011); p. 1947 - 1951 View in Reaxys

Ca. 90 %

With oxygen Guo, Hongfan; Kemell, Marianna; Al-Hunaiti, Afnan; Rautiainen, Sari; Leskelae, Markku; Repo, Timo; Catalysis Communications; vol. 12; nb. 13; (2011); p. 1260 - 1264 View in Reaxys

90 %

With [Pd(N,N'-bis(2,6-(diisopropyl)phenyl)imidazol-2-ylidene)(PCy3)], oxygen, acetic acid in toluene, Time= 15h, T= 60 °C , p= 760.051Torr , Molecular sieve Jurcik, Vaclav; Schmid, Thibault E.; Dumont, Quentin; Slawin, Alexandra M. Z.; Cazin, Catherine S. J.; Dalton Transactions; vol. 41; nb. 40; (2012); p. 12619 - 12623,5 View in Reaxys

90 %

With dihydrogen peroxide in water, acetonitrile, Time= 1.41667h, T= 25 °C Eshtiagh-Hosseini, Hossein; Tabari, Taymaz; Takjoo, Reza; Eshghi, Hossein; Synthesis and Reactivity in Inorganic, MetalOrganic and Nano-Metal Chemistry; vol. 43; nb. 3; (2013); p. 264 - 272

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View in Reaxys 90 %

With pivalaldehyde in toluene, Time= 0.5h, T= 40 °C , Flow reactor Chorghade, Rajeev; Battilocchio, Claudio; Hawkins, Joel M.; Ley, Steven V.; Organic Letters; vol. 15; nb. 22; (2013); p. 5698 - 5701 View in Reaxys

90 %

General Procedure General procedure: A mixture of benzylic alcohol (1.0mmol), urea hydrogen peroxide (1.5 mmol) and calciumchloride (0.5 mmol) was stirred in PEGDME250 (2 mL) at 70oC for 4 h. After cooling the mixture to room temperature theproduct is extracted into diethyl ether (3 × 20 mL), washedwith water and dried over MgSO4. The combined etherextracts were concentrated under reduced pressure and thecrude product was purified by flash column chromatography(ethyl acetate/n-hexane = 1:3, v/v) to give the desired carbonylcompound. With urea hydrogen peroxide adduct, calcium chloride, Time= 4h, T= 70 °C Ha, Su Jeong; Jung, Eun-Young; Kim, Won Mi; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 35; nb. 2; (2014); p. 629 - 630 View in Reaxys

90 %

4.1.24 : 4.1.2 Typical experimental procedure with HIO3 in the presence of TEMPO (Method B) General procedure: To a solution of 1-(p-bromophenyl)ethanol I-23 (201 mg, 1.0 mmol) in DMF (2.0 mL) was added HIO3 (194 mg, 1.1 mmol) and TEMPO (7.8 mg, 0.05 mmol). The mixture was stirred for 2 h at room temperature under an Ar atmosphere. After the reaction, the reaction mixture was poured into aq Na2S2O3, and extracted with a mixture of Et2O: hexane=1:1 (3*10 mL). Then, the organic layer was poured into satd NaCl (10 mL) and extracted with Et2O (10 mL). The organic layer was dried over Na2SO4. After being filtration and removal of the solvent under reduced pressure, the residue was purified by flash short column chromatography on silica gel (EtOAc-hexane, 1:4) to give p-bromoacetophenone II-23 in 99percent yield. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, iodic acid in N,N-dimethyl-formamide, Time= 2h, T= 20 °C , Inert atmosphere, Reagent/catalyst, Temperature Imai, Sho; Togo, Hideo; Tetrahedron; vol. 72; nb. 44; (2016); p. 6948 - 6954 View in Reaxys

90 %

With [Fe(1,1η-methylene-3,3η-di-benzylimidazole-2-ylidene)(bipy)I2] in neat (no solvent), Time= 6h, T= 80 °C , Inert atmosphere, Schlenk technique, Catalytic behavior Pinto, Mara F.; Cardoso, Bernardo De P.; Barroso, Sónia; Martins, Ana M.; Royo, Beatriz; Dalton Transactions; vol. 45; nb. 34; (2016); p. 13541 - 13546 View in Reaxys

90 %

With Iron(III) nitrate nonahydrate, oxygen, 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,2-dichloro-ethane, Time= 3h, T= 60 °C , Schlenk technique, Green chemistry Hu, Yongke; Chen, Lei; Li, Bindong; Catalysis Communications; vol. 103; (2018); p. 42 - 46 View in Reaxys

90 %

With N-Bromosuccinimide in dichloromethane, Time= 20h, T= -20 °C , Schlenk technique Sun, Jin-Shi; Jing, Li-Ping; Tian, Yuyang; Sun, Fuxing; Chen, Peng; Zhu, Guangshan; Chemical Communications; vol. 54; nb. 13; (2018); p. 1603 - 1606 View in Reaxys

89 %

With aluminum oxide, [bis(acetoxy)iodo]benzene, Time= 0.0333333h, microwave sonication Varma, Rajender S.; Dahiya, Rajender; Saini, Rajesh K.; Tetrahedron Letters; vol. 38; nb. 40; (1997); p. 7029 - 7032 View in Reaxys

89 %

With aluminum oxide, [bis(acetoxy)iodo]benzene, Time= 0.0333333h, T= 80 °C , Irradiation Varma, Rajender S.; Saini, Rajesh K.; Dahiya, Rajender; Journal of Chemical Research - Part S; nb. 3; (1998); p. 120 - 121 View in Reaxys

89 %

With sodium periodate in water, acetonitrile, Time= 1.66667h, T= 20 °C

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Saffar-Teluri, Ali; RSC Advances; vol. 5; nb. 86; (2015); p. 70577 - 70585 View in Reaxys 89 %

With tert.-butylhydroperoxide in hexane, water, Time= 10.5h, T= 50 °C Zhang, Yuecheng; Huo, Wenge; Zhang, Hong-Yu; Zhao, Jiquan; RSC Advances; vol. 7; nb. 75; (2017); p. 47261 - 47270 View in Reaxys

89 %

With sodium tungstate (VI) dihydrate, dihydrogen peroxide, tricaprylmethylammonium hydrogen sulfate in water, Time= 0.075h, T= 130 °C , p= 5250.53Torr , Flow reactor, Thermodynamic data Glotz, Gabriel; Knoechel, Donald J.; Podmore, Philip; Gruber-Woelfler, Heidrun; Kappe, C. Oliver; Organic Process Research and Development; vol. 21; nb. 5; (2017); p. 763 - 770 View in Reaxys

88 %

With potassium nitrososulfonate, adogen 464 in benzene, Time= 12h Morey, Jeronimo; Dzielenziak, Adam; Saa, Jose Manuel; Chemistry Letters; (1985); p. 263 - 264 View in Reaxys

88.7 %

With ruthenium(IV) oxide, tetrabutylammomium bromide, tetra(n-butyl)ammonium hydroxide in water, acetonitrile, electrooxidation on Pt electrodes Torii, Sigeru; Yoshida, Akihito; Chemistry Letters; nb. 5; (1995); p. 369 - 370 View in Reaxys

88 %

With dinitrogen tetraoxide, ferric nitrate in dichloromethane, Time= 0.25h, Ambient temperature, further oxidizing agent, further conditions and solvents Iranpoor, Nasser; Firouzabadi, Habib; Zolfigol, Mohammad Ali; Bulletin of the Chemical Society of Japan; vol. 71; nb. 4; (1998); p. 905 - 908 View in Reaxys

88 %

With DPE-Phos, potassium tert-butylate, carbonyl(dihydrido)tris(triphenylphosphine)ruthenium(II) in toluene, Time= 24h, Heating Wise, Nicola J.; Williams, Jonathan M.J.; Tetrahedron Letters; vol. 48; nb. 21; (2007); p. 3639 - 3641 View in Reaxys

88 %

General procedure for oxidation of alcohols: General procedure: Oven dried round bottom flask was charged with Eosin Y (5 mmol) alcohol (1 mmol) and 3 equiv. of TBHP (5.5 M in decane) in dry ACN. The resulting mixture was degassed for 15 mins, followed by back filling N2, and then irradiated under Blue LED light (12W, 455 nm) at room temperature (25 oC). After reaction completion monitored through TLC, the mixture was diluted with 15 ml of 10percent NaHCO3 solution, and extracted with EtOAc (3 × 20 ml). The combined organic extracts were washed with brine (20 ml), dried over Na2SO4, and concentrated on vacuo. Purification of the crude product on silica gel using EtOAc:Hexane as solvent system afforded the desired product. With tert.-butylhydroperoxide, eosin y in decane, acetonitrile, Time= 34h, T= 25 °C , Inert atmosphere, Irradiation, Molecular sieve, Green chemistry, chemoselective reaction Devari, Shekaraiah; Rizvi, Masood Ahmad; Shah, Bhahwal Ali; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3294 - 3297 View in Reaxys

88 %

With C29H35Cl2IrN2O2, sodium acetate in 2,2,2-trifluoroethanol, Time= 20h, Inert atmosphere, Reflux, Schlenk technique Gülcemal, Süleyman; Gülcemal, Derya; Whitehead, George F. S.; Xiao, Jianliang; Chemistry - A European Journal; vol. 22; nb. 30; (2016); p. 10513 - 10522 View in Reaxys

87 %

With montmorillonite K 10 clay supported iron(III) nitrate (clayfen), Time= 0.00833333h, microwave (900 Watts) irradiation at ca. 65 deg C Varma, Rajender S.; Dahiya, Rajender; Tetrahedron Letters; vol. 38; nb. 12; (1997); p. 2043 - 2044 View in Reaxys

87 %

With dihydrogen peroxide, Montmorillonite K10, manganese(ll) chloride in acetonitrile, Time= 2h, Heating

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Hashemi, Mohammed M.; Khalili, Behzad; Eftekhari-sis, Bagher; Journal of Chemical Research; nb. 8; (2005); p. 484 - 485 View in Reaxys 87 %

Stage 1: With (-N(SO2C8F17)-(biphenyl-2,2'-diyl)-O-)AlCH3 in toluene, Time= 0.5h, T= 21 °C Stage 2: With pivalaldehyde in toluene, Time= 1h, T= 21 °C , Oppenauer oxidation, Further stages. Ooi, Takashi; Otsuka, Hidehito; Miura, Tomoya; Ichikawa, Hayato; Maruoka, Keiji; Organic Letters; vol. 4; nb. 16; (2002); p. 2669 - 2672 View in Reaxys

87 %

With chromium (VI) oxide in toluene, T= 90 °C , Fixed-bed flow reactor, Inductive heating Wegner, Jens; Ceylan, Sascha; Friese, Carsten; Kirschning, Andreas; European Journal of Organic Chemistry; nb. 23; (2010); p. 4372 - 4375 View in Reaxys

87%

With 1-acetoxy-5-nitro-1H-1η3-benzo[d][1,2]iodoxol-3-one in N,N-dimethyl-formamide, Time= 24h, T= 65 °C Iinuma, Masataka; Moriyama, Katsuhiko; Togo, Hideo; Synlett; vol. 24; nb. 13; (2013); p. 1707 - 1711; Art.No: ST-2013U0386-L View in Reaxys

87 %

General Procedures for Copper-Catalyzed Secondary AlcoholOxidation under Reflux in Neat Water (1-Phenethyl Alcohol) General procedure: A mixture of 1-phenethyl alcohol (1.0 mmol), N-(phenyl)phenylalanine(0.0241 g, 0.1 mmol), CuBr2 (0.0223 g, 0.1 mmol),NaOAc (0.1640 g, 2.0 mmol), TEMPO (0.0156 g, 0.1 mmol), andH2O (3.0 mL) were placed into a 100 mL Schlenk tube, whichwas vigorously stirred in air under reflux for 12 h. After thereaction, the product was extracted with CH2Cl2 (3 × 2.0 mL).The combined organic phase was washed with H2O (3.0 mL) anddried over anhydrous MgSO4. After concentration undervacuum, the residue was purified by column chromatography toafford acetophenone.Isolated yield: 0.1080 g (90percent). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium acetate, (S)-3-phenyl-2-(phenylamino)propionic acid, copper(ll) bromide in water, Time= 24h, Reflux, Schlenk technique Zhang, Guofu; Lei, Jie; Han, Xingwang; Luan, Yuxin; Ding, Chengrong; Shan, Shang; Synlett; vol. 26; nb. 6; (2015); p. 779 - 784 View in Reaxys

86 %

With urea hydrogen peroxide adduct, 1-butyl-3-methylimidazolium Tetrafluoroborate, magnesium bromide, Time= 2h, T= 60 °C Heel, Joong Park; Jong, Chan Lee; Synlett; nb. 1; (2009); p. 79 - 80 View in Reaxys

86 %

With C16H13MnNO3*3H2O, dihydrogen peroxide in water, Time= 0.5h, T= 20 °C , Ionic liquid Rong, Meizhu; Wang, Juan; Shen, Yanping; Han, Jinyu; Catalysis Communications; vol. 20; (2012); p. 51 - 53 View in Reaxys

86 %

Experimental Procedures for oxidation of Various alcohols: General procedure: A CH3CN solution of alcohol (1 mmol), ZnBr2 (45 mg, 0.2 mmol), and chloramine-T (282 mg, 1 mmol) was placed in a three necked flask with a reflux condenser. After the mixture was stirred under reflux for 1.5-5 h. After cooling to room temperature, the solution was quenched by adding water and the resulting mixture was extracted with AcOEt. Removal of the solvent under reduced pressure gave the crude product, which was purified by column chromatography on silica gel to give the corresponding carbonyls. With chloroamine-T, zinc dibromide in acetonitrile, Time= 4.5h, Reflux Wang, Peng; Cai, Jin; Yang, Jiabin; Sun, Chunlong; Li, Lushen; Hu, Huayou; Ji, Min; Tetrahedron Letters; vol. 54; nb. 6; (2013); p. 533 - 535 View in Reaxys

86 %

General Procedure for Oxidation of Alcohols General procedure: Aromatic alcohol (1–2 mmol) was dissolved in methanol (or acetone in somecases, 2–4 mL) at room temperature, followed by addition of the aqueous solutionof N-bromosuccinimide (1.5 eq.=alcohol) with continuous stirring. GMP-bCD (3,100mg=mmol of alcohol) were added in the reaction mixture and stirring was continued.Progress of the reaction was

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monitored by TLC until the reaction was completed(4–6 h). GMP was separated by filtration after completion of the reaction. Thereaction mixture was extracted with ethyl acetate (45 mL), combined organiclayers were dried over Na2SO4, and solvent was removed under reduced pressure.The product was further purified by flash column chromatography and analyzedby NMR spectroscopy. With N-Bromosuccinimide in methanol, water, Time= 4h, T= 20 °C , Green chemistry Tahir, Muhammad Nazir; Qamar, Riaz-Ul; Adnan, Ahmad; Ghaffar, Abdul; Jun, Bong-Hyun; Yu, Jae-Hyuk; Jung, Seunho; Synthetic Communications; vol. 44; nb. 5; (2014); p. 589 - 599 View in Reaxys 86 %

With nickel(II) ferrite in toluene, Time= 6h, T= 120 °C , Green chemistry Payra, Soumen; Saha, Arijit; Banerjee, Subhash; RSC Advances; vol. 6; nb. 57; (2016); p. 52495 - 52499 View in Reaxys

86 %

With [Cu6(pyridine-2-thiolate)6], potassium hydroxide in toluene, Time= 24h, T= 70 °C , Schlenk technique, Glovebox, Inert atmosphere Tan, Da-Wei; Li, Hong-Xi; Zhang, Meng-Juan; Yao, Jian-Lin; Lang, Jian-Ping; ChemCatChem; vol. 9; nb. 6; (2017); p. 1113 - 1118 View in Reaxys

86 %

12 : Example 12: [Cu6 (pyt) 6]Catalytic dehydrogenation of 1-phenylacetone In the glove box, will be 1 - phenylpropanol (1.0 mmol), [Cu6 (Pyt)6 ] (0.08 mmol), KOH (1.0 mmol) is added to the test tube with the magnetic coil in the has, then adding 2.0 ml dry toluene solvent. After the sealed reaction tube, is taken out of the glove box. Toward the nozzle leads into the small and stable and low production, stable air flow after such as, for 70 °C reaction under 24 h; after the reaction, extracted with ethyl acetate (3 × 5 ml), the combined organic phase, dried with anhydrous sodium sulfate, filtered, concentrated filtrate for rotary evaporator, and then separating and purifying column law silica gel chromatography, to obtain the target product 1 - phenyl propanone (yield 86percent). With [Cu6(SC5H4N)6], potassium hydroxide in toluene, Time= 24h, T= 70 °C , Glovebox, Inert atmosphere Patent; Soochow University; Li, Hongxi; Tan, Dawei; Li, Haiyan; Lang, Jianping; (15 pag.); CN106588957; (2017); (A) Chinese View in Reaxys

85 %

With <Ce(NO3)3>2CrO4 in benzene, Time= 0.7h, Heating Firouzabadi, H.; Iranpoor, N.; Parham, H.; Tootan, J.; Synthetic Communications; vol. 14; nb. 7; (1984); p. 631 - 638 View in Reaxys

85 %

With tert.-butylhydroperoxide, [Co(4-nbz)2(py)2] in water, acetonitrile, Time= 4h, T= 82 °C Chakravorty, Stutee; Das, Birinchi K.; Polyhedron; vol. 29; nb. 8; (2010); p. 2006 - 2013 View in Reaxys

85 %

General Experimental Procedure for the Oxidation of Alcohols: General procedure: To a solution of the alcohol (1.0 mmol) and hydrogen peroxide(5.0 mmol, 30percent aq) was added BiBr3 (10 molpercent). The reactionmixture was stirred at 70 °C for 10–40 min, and thereaction mixture was extracted with dichloromethane (2 × 5mL). The combined organic layers were washed with saturatedbrine (2 × 5 mL) and dried with anhydrous MgSO4. After evaporationof the solvent, the residue was purified by flash columnchromatography (SiO2; CH2Cl2–hexane, 3:2) to afford the purecarbonyl compound. With bismuth(III) bromide, dihydrogen peroxide in water, Time= 0.166667h, T= 70 °C , Green chemistry Han, Mi-Kyung; Kim, Sohwa; Kim, Sung Tae; Lee, Jong Chan; Synlett; vol. 26; nb. 17; (2015); p. 2434 - 2436; Art.No: ST-2015-U0545-L View in Reaxys

85.3 %

With tert.-butylhydroperoxide, Time= 6h, T= 70 °C , Catalytic behavior Zhang, Yuecheng; Sun, Xiaochen; Zhang, Hongyu; Zhao, Jiquan; Applied Organometallic Chemistry; vol. 30; nb. 8; (2016); p. 645 - 652 View in Reaxys

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84 %

With manganese dioxide on silica gel, Time= 0.0166667h, Irradiation Varma, Rajender S.; Saini, Rajesh K.; Dahiya, Rajender; Tetrahedron Letters; vol. 38; nb. 45; (1997); p. 7823 - 7824 View in Reaxys

84 %

With oxygen, (nBu4N)4W10O32, silica gel in acetonitrile, Time= 1h, T= 25 °C , UV-irradiation Farhadi, Saeid; Afshari, Mozhgan; Journal of Chemical Research; nb. 3; (2006); p. 188 - 191 View in Reaxys

84 %

With iodine, oxygen in acetonitrile, Time= 4h, T= 20 °C , Irradiation Farhadi, Saeid; Zabardasti, Abedien; Babazadeh, Zaynab; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8953 - 8957 View in Reaxys

84 %

With 4-acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate in water, Time= 8h, Reflux Mamros, Audrey N.; Sharrow, Phillip R.; Weller, William E.; Luderer, Mark R.; Fair, Justin D.; Pazehoski, Kristina O.; Luderer, Matthew R.; Arkivoc; vol. 2011; nb. 5; (2011); p. 23 - 33 View in Reaxys

84 %

16 : Example 16 Equipped with a magnetic stirrer in round bottom flask methyl benzyl alcohol (12. 22g, 100. Ommol, namely formula The R1 is 4-methyl, R2 is hydrogen, X is carbon, η is 1, m is 0), ferric chloride (0. 81g, 5mmol), L- isoleucineAcid (1.31g, 10mmol), TEMP0 (1.56g, 10mmol), toluene 300. OmL was added , then the reaction with oxygen in the air bottleReplacement, stirred and reflux for 6h. After completion of reaction, the reaction mixture was cooled to room temperature, filtered, the filtrate evaporated to give the crude product,The resultant crude product was purified by column chromatography, with n-hexane: Elution: (10 1 volume ratio) mixed liquid of ethyl acetate containing the desired collectionLabeled compound of the eluent, evaporation of the solvent and dried to give the product p-tolualdehyde 10. 93g, 91percent yield. 1-phenyl-propanol (1. 36g, 10. Ommol, i.e., of formula (I) is hydrogen, R1 is 4, R2 is BGroup, X is carbon, [eta] is 1, m is 0) is taken, experimental methods and procedures were the same as in Example 1, except that: iron bromide (0.30 g,1. Ommol), 2-methyl-alanine (0 · 05g, 0 · 5mmol), TEMPO (0 · 16g, 1 · Ommol), dioxane 30. OmL, withThe reaction of oxygen bottle air displacement stirred at reflux for 48h. To give the final product 1. 13g, yield 84percent. With ferric(III) bromide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, 2-Aminoisobutyric acid in 1,4-dioxane, Time= 48h, Reflux, Green chemistry Patent; Zhejiang University; Zhang, Guofu; Li, Shasha; Ding, Chengrong; Zhang, Guihua; Xie, Xiaoqiang; Lei, Jie; (12 pag.); CN105294413; (2016); (A) Chinese View in Reaxys

83 %

With oxygen in benzene, T= 150 °C , p= 5250.53Torr Chaudhuri, Sangeeta Roy; Hartwig, Jan; Kupracz, Lukas; Kodanek, Torben; Wegner, Jens; Kirschning, Andreas; Advanced Synthesis and Catalysis; vol. 356; nb. 17; (2014); p. 3530 - 3538 View in Reaxys

83 %

With cesium hydroxide, {[(2-(sulfonylquinlium-8-yloxy)phthalic acid-2H)2Cu4(4,4η-bipyridine)4]·2H2O}n·2nH2O in acetonitrile, Time= 12h, T= 80 °C Feng, Xun; Xu, Chen; Wang, Zhi-Qiang; Tang, Si-Fu; Fu, Wei-Jun; Ji, Bao-Ming; Wang, Li-Ya; Inorganic Chemistry; vol. 54; nb. 5; (2015); p. 2088 - 2090 View in Reaxys

82 %

With pyridinium chlorochromate on alumina, Time= 2h, T= 20 °C Bhar, Sanjay; Chaudhuri, Subrata Kumar; Tetrahedron; vol. 59; nb. 19; (2003); p. 3493 - 3498 View in Reaxys

82 %

With tert.-butylhydroperoxide, Rh2(Msip)4, sodium hydrogencarbonate in dichloromethane, water, Time= 24h, T= 40 °C , Sealed tube, chemoselective reaction Wusiman, Abudureheman; Lu, Chong-Dao; Applied Organometallic Chemistry; vol. 29; nb. 4; (2015); p. 254 - 258 View in Reaxys

81 %

With Et3N-WS-TEMPO bromide in water, T= 0 °C , Electrochemical reaction

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Kubota, Jun; Shimizu, Yusuke; Mitsudo, Koichi; Tanaka, Hideo; Tetrahedron Letters; vol. 46; nb. 52; (2005); p. 8975 - 8979 View in Reaxys 81 %

With anionic TEMPO in water, T= 20 °C , Electrochemical reaction Mitsudo, Koichi; Kumagai, Hiroki; Takabatake, Fumiko; Kubota, Jun; Tanaka, Hideo; Tetrahedron Letters; vol. 48; nb. 51; (2007); p. 8994 - 8997 View in Reaxys

81 %

Stage 1: With titanium tetrachloride in chloroform, Time= 1h, T= 20 °C , Molecular sieve Stage 2: With tert.-butylhydroperoxide in chloroform, toluene, Time= 24h, T= 20 °C , chemoselective reaction Shei, Chun-Tin; Chien, Hao-Lun; Sung, Kuangsen; Synlett; nb. 7; (2008); p. 1021 - 1026 View in Reaxys

81 %

Typical procedure for the oxidation of alcohols General procedure: To a solution of alcohol (0.1 mmol) in 10 ml of solvent were added Oxone (1.5 mmol), FeSO4·7H2O (5 mol percent) and GO (0.05 g). The resulting mixture was irradiated with an ultrasonic probe for the time indicated in Table 2. The mixture was filtered through a sintered funnel and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. Purification was achieved by recrystallization from EtOAc/n-hexane or by column chromatography using n-hexane/EtOAc: 9:1 as eluent (for entries 2, 4 and 11). The spectroscopic data of the obtained acids were compared with authentic samples. With ferrous(II) sulfate heptahydrate, Oxone in water, Time= 0.5h, T= 20 °C , Sonication, Green chemistry Mirza-Aghayan, Maryam; Molaee Tavana, Mahdieh; Boukherroub, Rabah; Tetrahedron Letters; vol. 55; nb. 2; (2014); p. 342 - 345 View in Reaxys

81 %

General procedure for the oxidation of alcohols with molecular iodine and potassium tertbutoxide General procedure: (Tables 1 and 2, Scheme 1). In a typical run, a reaction flask (25 mL) was chargedwith an indicated amount of I2 (typically, 508 mg, 2 mmol) and potassium tert-butoxide(typically, 470 mg, 4.2 mmol). The mixture was suspended in CH2Cl2 (5 mL) and stirred at 10 oCfor 30 min, then alcohol (1 mmol) was added. The mixture was continually stirred at an indicatedtemperature (typically, at 10 °C) until the consumption of the alcohol (monitoring with TLC,typically, for a few hours), then diluted with CH2Cl2 (10 mL) and washed with saturated aqueoussodium thiosulfate (10 mL). The aqueous phase was extracted with CH2Cl2 (three portions of 10mL each). The combined organic phase was washed with deionized water and saturated aqueousNaCl, dried over anhydrous Na2SO4, and then filtered and concentrated. The crude product waspurified by column chromatography (silica, hexane or hexane/EtOAc mixture as eluent). Theyields are listed in Tables 1 and 2 as well as Scheme 1. With potassium tert-butylate, iodine in dichloromethane, Time= 4h, T= -20 °C Luo, Qun-Li; Nan, Wen-Hui; Li, Yu; Chen, Xiang; Arkivoc; vol. 2014; nb. 4; (2014); p. 350 - 361 View in Reaxys

80 %

With cerous hydroxide in benzene, Time= 1h, Heating Firouzabadi, H.; Iranpoor, N.; Synthetic Communications; vol. 14; nb. 9; (1984); p. 875 - 882 View in Reaxys

80.2 %

With tris(triphenylphosphine)ruthenium(II) chloride, potassium carbonate, acetone, Time= 12h, T= 56 °C Wang, G-Z.; Baeckvall, Jan-E.; Journal of the Chemical Society, Chemical Communications; nb. 4; (1992); p. 337 - 339 View in Reaxys

80 %

With sodium carbonate, acetone, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt, bis(1,5-cyclooctadiene)diiridium(I) dichloride in water, Time= 4h, T= 90 °C , Oppenauer-type oxidation Ajjou, Abdelaziz Nait; Tetrahedron Letters; vol. 42; nb. 1; (2001); p. 13 - 16 View in Reaxys

80 %

With allyltriphenylphopsphonium peroxodisulfate in acetonitrile, Time= 0.666667h, Heating Tajbakhsh; Lakouraj; Fadavi; Synthetic Communications; vol. 34; nb. 7; (2004); p. 1173 - 1181 View in Reaxys

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80 %

With sodium carbonate, acetone, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt, bis(1,5-cyclooctadiene)diiridium(I) dichloride in water, Time= 4h, T= 90 °C Ajjou, Abdelaziz Nait; Pinet, Jean-Louis; Canadian Journal of Chemistry; vol. 83; nb. 6-7; (2005); p. 702 - 710 View in Reaxys

80.3 %

With tert.-butylhydroperoxide, [O-Cu4(triethanolamine)4(BOH)4][BF4]2 in acetonitrile, Time= 6h, T= 69.84 °C Zhu, Mingxia; Li, Bodong; He, Ping; Wei, Xin; Yuan, Youzhu; Tetrahedron; vol. 64; nb. 39; (2008); p. 9239 - 9243 View in Reaxys

80 %

With N-Bromosuccinimide, 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea in dichloromethane, Time= 90h, T= -20 °C , Inert atmosphere Tripathi, Chandra Bhushan; Mukherjee, Santanu; Journal of Organic Chemistry; vol. 77; nb. 3; (2012); p. 1592 - 1598 View in Reaxys

80 %

Typical experimental procedure for the synthesis of Piperonal: (entry 4, Table 1) In a typical experimental procedure a mixture of benzo[d][1,3]dioxol-5-ylmethanol (1 mmol, 152 mg), NaIO4 (1 mmol, 213 mg) in 2 ml of DCM was taken in an open round bottomed flask at room temperature and then NH2OH*HCl (1.5 mmol, 105 mg) was added by portion for 5 min. After completion (TLC), the reaction mixture was diluted with a 1:1 mixture of water/DCM (10 mL) and washed with 10percent (w/v) Na2S2O3 (3 .x. 5 ml). Then the combined organic layer was dried over anhydrous Na2SO4. Evaporation of solvent furnished the crude product which was subjected to column chromatography using ethyl acetate-petroleum ether (1:10) to obtain the analytically pure product as a white solid (122 mg, 80percent). With sodium periodate, hydroxylamine hydrochloride in dichloromethane, T= 20 °C , chemoselective reaction Majee, Adinath; Kundu, Shrishnu Kumar; Santra, Sougata; Hajra, Alakananda; Tetrahedron Letters; vol. 53; nb. 33; (2012); p. 4433 - 4435 View in Reaxys

80 %

With sodium tungstate (VI) dihydrate, dihydrogen peroxide, tricaprylmethylammonium hydrogen sulfate in water, T= 135 °C , Sealed tube, Microwave irradiation Obermayer, David; Znidar, Desiree; Glotz, Gabriel; Stadler, Alexander; Dallinger, Doris; Oliver Kappe; Journal of Organic Chemistry; vol. 81; nb. 23; (2016); p. 11788 - 11801 View in Reaxys

79 %

Oxidation of p-chlorobenzyl alcohol (Table 1, entry 5). Typical procedure: To a solution of p-chlorobenzyl alcohol (143.4 mg, 1.01 mmol) in CH2Cl2 (10 mL) was added K-birnessite (2.98 g). The reaction mixture was stirred at 30 °C for 7 h. Black precipitate was removed by filtration over celite. The filtrate was concentrated to give crude p-benzaldehyde, which was purified through flash chromatography (silica gel/hexane-EtOAc) to give 2c in 90percent yield (129.1 mg). With K-birnessite MnO2 in dichloromethane, Time= 3h, T= 30 °C Kamimura, Akio; Nozaki, Yuichiro; Ishikawa, Shingo; Inoue, Ryota; Nakayama, Masaharu; Tetrahedron Letters; vol. 52; nb. 4; (2011); p. 538 - 540 View in Reaxys

78 %

A.4 :EXAMPLESThe following examples exemplify oxidation reactions on a laboratory scale that were carried out with the inventive process in a flow-through reactor. The present invention is of course not limited to these.Glass tubes with a length of 12 cm and an internal diameter of 8.5 mm were used as the tubular reactor. The tubes were provided with screw connections on both ends so as to be able to attach the HPLC and suitable tubing. After having filled the reactor, the free internal volume for the fluid was 4 ml. For experiments under pressure (example group B and example 4 of the example group C), a PEEK (polyether ether ketone) reactor having the same dimensions was used and was equipped with a reaction pressure regulator. In the following reaction schemes the reactor in the inductor is indicated with the designated graphic symbol "1".The inductor had the following performance characteristics: inductivity: 134 μHenry, winding count for the spool:=16, cross sectional area=2.8 mm2 (the cross sectional area results from the number of the conductor wires in the inductor and their diameter.) The diameter of the gap for receiving the tubular reactor was 12 mm. For all experiments the inductor was operated with a frequency of 25 kHz.In the experiments the specified frequency of 25 kHz was left constant and the heating control was undertaken solely through the PWM (PWM=on/off switch for a square wave signal at a fixed fundamental frequency). In addition, the PWM is given in .per mil. and/or the achieved reaction temperatures in ° C. The induced temperature was measured with a thermocouple and an infrared thermometer. The thermocouple was mounted directly behind the reactor in the fluid so as to permit an accurate as possible

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measurement. However, due to the metallic components of the thermocouple, a minimum distance of 4 cm had to be observed. A laser infrared thermometer with close focus optics was used for the second temperature measurement. The measurement point had a diameter of 1 mm. With this method the surface temperature of the reactor should be measured in order to obtain a second measurement point for the temperature determination. The emission factor of the material is an important constant for an infrared measurement. It is a measure of the heat emission. An emission factor of 0.85 was used and corresponds to that of an average glass.For the example groups A and B, particles of CrO2 were employed as the oxygen carrier; they can be obtained by heating Cr(III) oxide at 300° C. in an oxygen atmosphere for 2 hours. The length and diameter of the particles were approx. 0.3 μm and approx. 0.03 μm respectively. The surface area determined by BET (nitrogen) was approx. 30 m2/g. A commercial product is available under the name MagTrieve.(TM). These particles are themselves not heatable by electromagnetic induction. They were therefore employed as the heating medium in a mixture with manganese ferrite powder (reaction example A1) and in a mixture with MagSilica.(TM). (each in the volume ratio 1:1) for the other reaction examples.For the example group C, particles of NiO2 (nickel peroxide) mixed with MagSilica.(TM). (each in the volume ratio 1:1) as the heating medium.For each reaction the reactor, charged with the oxidizing agent and the heating medium was inserted into the inductor and connected on the inlet side with a pump, on the outlet side with a collection vessel. Initially, toluene was pumped through the reactor until constant flow conditions were obtained. The reaction temperature was then adjusted by regulating the power of the inductor. Once a constant temperature was reached the reaction solution was fed through the reactor. The reaction temperatures and the flow rates as well as the isolated yields are given for the individual examples (yields after distilling off the solvent under vacuum and downstream processing of the residue by flash chromatography (SiO2, ethyl acetate/petroleum ether). The products were identified from their 1H nuclear magnetic resonance spectra and further analytical literature data. The listed yields were each obtained with a single pass of the reactants.Reaction Examples Group A:The starting products were introduced as a solution in toluene (0.15 molar). Comparative: For preparing the target products in the batch process, the following yields were obtained: Product 3: 46percent after 7 hours, Product 5: 95percent after 22 hours, Product 7: 62percent after 7 hours, Product 9: 95percent after 7 hours. Furthermore, the downstream processing (product separation from the heating medium and oxidizing agent) in the inventive process is considerably easier, as the filtration and washing steps are obviated. This applies to all reaction examples. With chromium (VI) oxide in toluene, T= 90 °C Patent; Henkel AG and Co. KGaA; US2011/301363; (2011); (A1) English View in Reaxys 77 %

With 2-Picolinic acid, manganese(II) perchlorate hexahydrate, dihydrogen peroxide, sodium acetate in acetonitrile, T= 0 - 20 °C Dong, Jia Jia; Unjaroen, Duenpen; Mecozzi, Francesco; Harvey, Emma C.; Saisaha, Pattama; Pijper, Dirk; De Boer, Johannes W.; Alsters, Paul; Feringa, Ben L.; Browne, Wesley R.; ChemSusChem; vol. 6; nb. 9; (2013); p. 1774 - 1778 View in Reaxys

76 %

With manganese(IV) oxide in hexane, Time= 8h, Ambient temperature Tsuboi, Sadao; Ishii, Naomi; Sakai, Takashi; Tari, Isao; Utaka, Masanori; Bulletin of the Chemical Society of Japan; vol. 63; nb. 7; (1990); p. 1888 - 1893 View in Reaxys

76 %

With sodium hypochlorite, sodium hydrogencarbonate, potassium bromide, molecularly imprinted polymeric nitroxide catalyst in dichloromethane, Time= 2h, T= 0 °C Anderson, Christopher D.; Shea, Kenneth J.; Rychnovsky, Scott D.; Organic Letters; vol. 7; nb. 22; (2005); p. 4879 - 4882 View in Reaxys

75 %

With mercury(II) oxide in acetonitrile, T= 25 °C , UV-irradiation Habibi; Farhadi; Polish Journal of Chemistry; vol. 78; nb. 5; (2004); p. 741 - 744 View in Reaxys

75 %

With silica supported nickel peroxide, Time= 0.0833333h, neat (no solvent) Kooti, Mohammad; Amirian, Soodabeh; E-Journal of Chemistry; vol. 8; nb. 2; (2011); p. 491 - 494 View in Reaxys

75 %

With C26H30F6MnN6O6S2, dihydrogen peroxide, acetic acid in acetonitrile, Time= 1h, T= 20 °C , chemoselective reaction Shen, Duyi; Miao, Chengxia; Xu, Daqian; Xia, Chungu; Sun, Wei; Organic Letters; vol. 17; nb. 1; (2015); p. 54 - 57 View in Reaxys

75 %

Dehydrogenative oxidation of various secondary alcohols shown in Table 2:

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General procedure: In a flask under argon atmosphere, iridium catalyst 5 (0.50 or 1.0 mol percent), sodium hydroxide (0.50 or 1.0 mol percent), water (2 mL), and alcohol (2.0 mmol) were placed. The mixture was stirred under vigorous reflux (temperature of the oil bath was set at 140 °C) for 20-96 h. After cooling to room temperature, water (4 mL) was added and the mixture was transferred to a separate funnel. Extraction of the organic compounds with dichloromethane (15 mL x 3), dehydration with sodium sulfate, followed by evaporation under vacuum gave crude mixture. For entries 2-11,the conversion of starting alcohol and the yield of ketone were determined by 1H NMR analysis in chloroform-d using triphenylmethane as an internal standard. For entries 1 and 12-14, the conversion of starting alcohol and the yield of ketone were determined by GC analysis using biphenyl as an internal standard. For entries 2-8, 10, and 11, the product was isolated by silica-gel column chromatography (eluent:ethyl acetate/ hexane). With C19H20IrNO2, sodium hydroxide in water, Time= 48h, T= 140 °C , Inert atmosphere Toyomura, Kazuki; Fujita, Ken-Ichi; Chemistry Letters; vol. 46; nb. 6; (2017); p. 808 - 810 View in Reaxys 74 %

With tert.-butylhydroperoxide, 4 A molecular sieve in tetrachloromethane, 2,2,4-trimethylpentane, Time= 96h, T= 60 °C Palombi, Laura; Arista, Luca; Lattanzi, Alessandra; Bonadies, Francesco; Scettri, Arrigo; Tetrahedron Letters; vol. 37; nb. 43; (1996); p. 7849 - 7850 View in Reaxys

74 %

With tert.-butylhydroperoxide, 4 A molecular sieve in tetrachloromethane, 2,2,4-trimethylpentane, Time= 96h, T= 50 °C Palombi, Laura; Bonadiesa, Francesco; Scettri, Arrigo; Tetrahedron; vol. 53; nb. 46; (1997); p. 15867 - 15876 View in Reaxys

72 %

With oxygen, Ni-Al hydrotalcite in toluene, Time= 7h, T= 90 °C Choudary; Kantam, M. Lakshmi; Rahman, Ateeq; Reddy, Ch. Venkat; Rao, K. Koteswara; Angewandte Chemie - International Edition; vol. 40; nb. 4; (2001); p. 763 - 766 View in Reaxys

71 %

With pyridine, 1,4-diaza-bicyclo[2.2.2]octane, tetraethylammonium trichloride in acetonitrile, Ambient temperature Schlama, Thierry; Gabriel, Kiroubagaranne; Gouverneur, Veronique; Mioskowski, Charles; Angewandte Chemie (International Edition in English); vol. 36; nb. 21; (1997); p. 2342 - 2344 View in Reaxys

70 %

With hydrogenchloride, platinum, sodium chloride in chloroform, water, T= 30 °C , Electrolysis Bosco, A. John; Lawrence; Christopher; Radhakrishnan; Joseph Rosario, A. Arul; Raja; Vasudevan; Journal of Physical Organic Chemistry; vol. 28; nb. 9; (2015); p. 591 - 595 View in Reaxys

70 %

2.2. General procedure for the aerobic oxidation of various substrates General procedure: To a dried 45 mL tube equipped with a magnetic stirring, 2 mL acetonitrile, 0.5 mmol substrate and 0.046 mmol NO2 were sequentially added (note: the air in the tube was not removed). Then the reaction tube was sealed and stirred magnetically at a constant-temperature to perform the reaction for 5 h. Once the reaction time was reached, GCanalysis of the mixture provided the GC yields of the products. Then the crude product from another parallel experiment was purified by silicagel chromatography to give the desired product. With Nitrogen dioxide in acetonitrile, Time= 5h, T= 140 °C , p= 760.051Torr , Sealed tube Ren, Fangping; Tian, Xinzhe; Ren, Yun-Lai; Zhao, Shuang; Wang, Jianji; Zhao, Bo; Catalysis Communications; vol. 101; (2017); p. 98 - 101 View in Reaxys

66 %

With tetrabutylammomium bromide, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dichloromethane, water, Time= 4h, T= 20 °C Kuhakarn, Chutima; Kittigowittana, Krisada; Ghabkham, Pattama; Pohmakotr, Manat; Reutrakul, Vichai; Synthetic Communications; vol. 36; nb. 19; (2006); p. 2887 - 2892 View in Reaxys

66 %

General Experimental Procedure

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General procedure: The starting 1-(paratolyl)ethanol (1 mmol), chloramine-T (1 mmol), and In(OTf)3(0.3 mmol) were dissolved in CH3CN (10 mL) in a 100 mLflask equipped with a magnetic stirrer and a reflux condenser.The reaction mixture was heated at reflux for 3 h under anArgon atmosphere and was monitored for completion by TLC.After the reaction mixture was cooled to room temperature,the solvent was removed via rotary evaporation. The residueof the reaction mixture was separated through flash columnchromatography on silica gel. The obtained product was confirmed by spectroscopy. With indium(III) triflate, chloroamine-T in acetonitrile, Time= 3h, Reflux, Inert atmosphere Nakahara, Kazuhide; Kitazawa, Chie; Mineno, Tomoko; Chemical and Pharmaceutical Bulletin; vol. 65; nb. 8; (2017); p. 801 - 804 View in Reaxys 65 %

With oxygen, pivalaldehyde, (Me4N)[Co(L)]*2H2O (L = o-phenylenebis(N'-methyloxamidate) in acetonitrile, Time= 8h, T= 20 °C Fernandez, Isabel; Pedro, Jose R.; Rosello, Antonio L.; Ruiz, Rafael; Castro, Isabel; Ottenwaelder, Xavier; Journaux, Yves; European Journal of Organic Chemistry; nb. 7; (2001); p. 1235 - 1247 View in Reaxys

65 %

2.5. Typical procedure for alcohol oxidation General procedure: The reaction mixture of Primary or secondary alcohol (1 mmol),RuIIICl2 (AsPh3)2 (Ph-DPMP) Schiff base complex (0.1 mmol), NMO(1.1 mmol) and dichloromethane (2 mL) was stirred at room temperature.The filtrate obtained was evaporated under reduced pressureand the residual mass was dissolved in a mixture of ethylacetate/hexane (1:4) and then passed through a short column ofsilica gel using hexane/ethyl acetate (4:1) as eluent. Removal ofsolvent and usual workup gave the corresponding aldehydes andketones, which were identified by comparing their physical andspectral data with those of authentic compounds reported in literature[27]. With RuCl2(AsPh3)2(Ph-DPMP), 4-methylmorpholine N-oxide in dichloromethane, Time= 1.41667h, T= 20 °C Raja, K. Kanmani; Indra Gandhi; Lekha; Easwaramoorthy; Rajagopal; Journal of Molecular Structure; vol. 1060; nb. 1; (2014); p. 49 - 57 View in Reaxys

63 %

With dipyridinium dichromate, adogen 464, dihydrogen peroxide, sodium carbonate in various solvent(s), Time= 24h, Heating, Oxidation Delaval, Nicolas; Bouquillon, Sandrine; Henin, Francoise; Muzart, Jacques; Journal of Chemical Research - Part S; nb. 4; (1999); p. 286 - 287 View in Reaxys

63 %

With [MnIV 2 (μ-O)3(1,4,7-trimethyl-1,4,7-triazacyclononane)2](PF6)2, dihydrogen peroxide, trichloroacetic acid in water, acetonitrile, Time= 16h, T= 20 °C Saisaha, Pattama; Buettner, Lea; Van Der Meer, Margarethe; Hage, Ronald; Feringa, Ben L.; Browne, Wesley R.; De Boer, Johannes W.; Advanced Synthesis and Catalysis; vol. 355; nb. 13; (2013); p. 2591 - 2603 View in Reaxys

62 %

With sodium in tetrahydrofuran, Time= 18h, T= 20 °C Zhou, Li-Hong; Yu, Xiao-Qi; Pu, Lin; Tetrahedron Letters; vol. 51; nb. 3; (2010); p. 475 - 477 View in Reaxys

57 %

With nitric acid in nitromethane, Time= 3.33333h, T= 60 °C Gasparrini, F.; Giovannoli, M.; Misiti, D.; Natile, G.; Palmieri, G.; Synthetic Communications; vol. 18; nb. 1; (1988); p. 69 76 View in Reaxys

55 %

With 6-methyl-2-pyridinecarboxylic acid, 4-chloropicolinic acid, dihydrogen peroxide, iron(II) acetate in acetonitrile, Time= 0.5h, T= 25 °C Tanaka, Shinji; Kon, Yoshihiro; Ogawa, Atsuko; Uesaka, Yumiko; Tamura, Masanori; Sato, Kazuhiko; ChemCatChem; vol. 8; nb. 18; (2016); p. 2930 - 2938 View in Reaxys

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51 %

With 10% rhodium on carbon, sodium carbonate in water, Time= 6h, T= 100 °C , Inert atmosphere Sawama, Yoshinari; Morita, Kosuke; Yamada, Tsuyoshi; Nagata, Saori; Yabe, Yuki; Monguchi, Yasunari; Sajiki, Hironao; Green Chemistry; vol. 16; nb. 7; (2014); p. 3439 - 3443 View in Reaxys

50 %

With poly(1,4-phenylene-2,5-pyridinedicarboxyamide) supported periodic acid in acetonitrile, Time= 1.5h, Reflux Pourali, Ali Reza; Tabaean, Mehrosadat; Nazifi, S. Mohamad Reza; Chinese Chemical Letters; vol. 23; nb. 1; (2012); p. 21 24 View in Reaxys

45 %

With oxygen in toluene, Time= 7h, T= 110 °C Kamimura, Akio; Nozaki, Yuichiro; Nishiyama, Mai; Nakayama, Masaharu; RSC Advances; vol. 3; nb. 2; (2013); p. 468 472 View in Reaxys

28 %

With palladium dichloro <1,1'-bis(diphenylphosphino)ferrocene>, sodium t-butanolate in 1,4-dioxane, Time= 18h, T= 110 °C Bouteiller, Cedric; Becerril-Ortega, Javier; Marchand, Patrice; Nicole, Olivier; Barre, Louisa; Buisson, Alain; Perrio, Cecile; Organic and Biomolecular Chemistry; vol. 8; nb. 5; (2010); p. 1111 - 1120 View in Reaxys

20 %

With bis(pentafluorophenyl)borinic acid, magnesium sulfate, pivalaldehyde in toluene, Time= 5h, Ambient temperature Ishihara, Kazuaki; Kurihara, Hideki; Yamamoto, Hisashi; Journal of Organic Chemistry; vol. 62; nb. 17; (1997); p. 5664 5665 View in Reaxys

10 %

With carbon dioxide, oxygen, T= 130 °C , p= 75007.5Torr , Supercritical conditions Chapman, Adrian O.; Akien, Geoffrey R.; Arrowsmith, Nicholas J.; Licence, Peter; Poliakoff, Martyn; Green Chemistry; vol. 12; nb. 2; (2010); p. 310 - 315 View in Reaxys

Stage 1: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium hydrogencarbonate, sodium carbonate, Time= 2h, T= 20 °C , aq. buffer, Electroliysis Stage 2: With Amberlite IR 120, Time= 0.5h, aq. buffer Kuroboshi, Manabu; Yoshida, Tomonori; Oshitani, Jun; Goto, Kuniaki; Tanaka, Hideo; Tetrahedron; vol. 65; nb. 34; (2009); p. 7177 - 7185 View in Reaxys

With manganese(III) triacetate dihydrate, 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, Time= 12h, T= 22 °C Cosner, Casey C.; Cabrera, Pablo J.; Byrd, Katherine M.; Adams Thomas, Asia M.; Helquist, Paul; Organic Letters; vol. 13; nb. 8; (2011); p. 2071 - 2073 View in Reaxys With chromic acid Wagner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 16; (1884); p. 325; Chemische Berichte; 17 Ref. <1884>, 317 View in Reaxys With chloroform, dinitrogen tetraoxide Grundy; Journal of the Chemical Society; (1957); p. 5087 View in Reaxys

45 % Chromat.

With NH-pyrazole, air, sodium hydride in tetrahydrofuran, Time= 7h, Ambient temperature Ohta, Shunsaku; Tachi, Takao; Okamoto, Masao; Synthesis; nb. 4; (1983); p. 291 - 293 View in Reaxys

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98 % Turnov.

With dipyridinium dichromate, dihydrogen peroxide, sodium carbonate, adogen 464 in 1,2-dichloro-ethane, Time= 24h, T= 80 °C Muzart, Jacques; Ajjou, Abdelaziz N'Ait; Ait-Mohand, Samia; Tetrahedron Letters; vol. 35; nb. 13; (1994); p. 1989 - 1990 View in Reaxys

96 % Chromat.

With acetyl nitrate on montmorillonite K10, Time= 2h, Ambient temperature De Oliveira Filho; Moreira; Moran, Paulo J. S.; Rodrigues, J. Augusto R.; Tetrahedron Letters; vol. 37; nb. 29; (1996); p. 5029 - 5032 View in Reaxys With potassium iodide in water, tert-butyl alcohol, T= 20 °C , electrochemical conditions, Yield given Belmant, Christian; Cognet, Patrick; Berlan, Jacques; Lacoste, Germain; Fabre, Paul-Louis; Jud, Jean-Marc; Bulletin de la Societe Chimique de France; vol. 134; nb. 2; (1997); p. 159 - 166 View in Reaxys bei der Oxydation Wagner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 16; (1884); p. 322; Chemische Berichte; 17 Ref. <1884>, 317 View in Reaxys With tris(triphenylphosphine)ruthenium(II) chloride in various solvent(s), Time= 3h, T= 180 °C , Product distribution Pri-Bar, Ilan; Buchman, Ouri; Schumann, Hebert; Kroth, Heinz J.; Blum, Jochanan; Journal of Organic Chemistry; vol. 45; nb. 22; (1980); p. 4418 - 4428 View in Reaxys With tert.-butylhydroperoxide, chromium aluminophosphate-5 in chlorobenzene, Time= 7h, T= 85 °C , other secondary alcohols, other reagent, var. temp. and time, Product distribution Chen, Ji Dong; Dakka, Jihad; Neeleman, Ernst; Sheldon, Roger A.; Journal of the Chemical Society, Chemical Communications; nb. 18; (1993); p. 1379 - 1380 View in Reaxys in water, Ambient temperature, Irradiation, η-radiolysis; effect of added organic solvents (MeOH, CH3CN) in water on the Gvalue for the product formation Kuroda, Tokuyuki; Hisamura, Koji; Matsukuma, Ikuo; Nishikawa, Hiroshi; Nakamizo, Nobuhiro; Bulletin of the Chemical Society of Japan; vol. 62; nb. 3; (1989); p. 674 - 681 View in Reaxys With ruthenium(IV) oxide, tetrabutylammomium bromide, tetra(n-butyl)ammonium hydroxide in water, acetonitrile, electrooxidation on Pt electrodes; other alcohols, other solvent, Product distribution Torii, Sigeru; Yoshida, Akihito; Chemistry Letters; nb. 5; (1995); p. 369 - 370 View in Reaxys With tert.-butylhydroperoxide, oxygen, CrAPO-5 in chlorobenzene, Time= 19h, T= 110 °C , oxidation of primary and secondary alcohols with TBHP and O2 catalyzed with chromium-substituted aluminophosphates; conversion; selectivity; possible mechanism, Product distribution Chen, Ji Dong; Lempers, Hans E. B.; Sheldon, Roger A.; Journal of the Chemical Society - Faraday Transactions; vol. 92; nb. 10; (1996); p. 1807 - 1813 View in Reaxys With 2,6-dimethylpyridine, chiral nitroxyl radical in acetonitrile, T= 20 °C , Electrochemical reaction, NaClO4 supporting electrolyte; C/Pt electrodes; ref: Ag/AgCl, Oxidation, electrocatalytic oxidation Kashiwagi, Yoshitomo; Kurashima, Futoshi; Kikuchi, Chikara; Anzai, Jun-ichi; Osa, Tetsuo; Bobbitt, James M.; Tetrahedron Letters; vol. 40; nb. 35; (1999); p. 6469 - 6472 View in Reaxys

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28 % Chromat.

With Geotrichum candidum IFO 4597 cells in water, Time= 24h, T= 30 °C , Oxidation Nakamura, Kaoru; Inoue, Yuko; Matsuda, Tomoko; Misawa, Ibuki; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2397 - 2402 View in Reaxys

92 % Spectr.

With 3,3-dimethyldioxirane in acetone, T= 25 °C , Rate constant Baumstark, Alfons L.; Kovac, Franci; Vasquez, Pedro C.; Canadian Journal of Chemistry; vol. 77; nb. 3; (1999); p. 308 - 312 View in Reaxys

54 % Chromat.

With 4 A molecular sieve, oxygen, p-Toluic acid, bis(acetylacetonato)dioxidomolybdenum(VI), copper(II) nitrate in toluene, T= 100 °C , Oxidation Lorber, Christian Y.; Smidt, Sebastian P.; Osborn, John A.; European Journal of Inorganic Chemistry; nb. 4; (2000); p. 655 658 View in Reaxys

100 % Chromat.

With iodosylbenzene, potassium bromide in water, Time= 4h, Oxidation Tohma, Hirofumi; Takizawa, Shinobu; Maegawa, Tomohiro; Kita, Yasuyuki; Angewandte Chemie - International Edition; vol. 39; nb. 7; (2000); p. 1306 - 1308 View in Reaxys With oxoammonium resin in dichloromethane, Time= 2h, T= 20 °C Weik, Steffen; Nicholson, Graeme; Jung, Gnther; Rademann, Jrg; Angewandte Chemie - International Edition; vol. 40; nb. 8; (2001); p. 1436 - 1439 View in Reaxys With tert.-butylhydroperoxide, tetrabutyl-ammonium chloride, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt, sodium carbonate in water, Time= 24h, T= 20 °C Ferguson, Gabriel; Ajjou, Abdelaziz Nait; Tetrahedron Letters; vol. 44; nb. 51; (2003); p. 9139 - 9142 View in Reaxys With amberlyst-15, 3-phenyl-propenal, 2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene, Time= 0.666667h, T= 110 °C , microwave irradiation Sinha, Arun K.; Sharma, Anuj; Swaroop, Anand; Kumar, Vinod; Tetrahedron; vol. 63; nb. 4; (2007); p. 1000 - 1007 View in Reaxys

99 % Chromat.

With oxygen, potassium carbonate, Pd<*>SBA-15 in toluene, Time= 17h, T= 80 °C , p= 760Torr Karimi, Babak; Abedi, Sedigheh; Clark, James H.; Budarin, Vitaly; Angewandte Chemie - International Edition; vol. 45; nb. 29; (2006); p. 4776 - 4779 View in Reaxys With 3-chloro-benzenecarboperoxoic acid, potassium bromide, iodobenzene in acetonitrile, Time= 0.666667h, T= 20 °C Yamamoto, Yukiharu; Kawano, Yuhta; Toy, Patrick H.; Togo, Hideo; Tetrahedron; vol. 63; nb. 22; (2007); p. 4680 - 4687 View in Reaxys

99 % Chromat.

With tert.-butylhydroperoxide, [(Me3tacn)Ru(CF3CO2)2(H2O)]CF3CO2-SiO2 in hexane, Time= 16h, T= 45 °C Cheung, Wai-Hung; Yu, Wing-Yiu; Yip, Wing-Ping; Zhu, Nian-Yong; Che, Chi-Ming; Journal of Organic Chemistry; vol. 67; nb. 22; (2002); p. 7716 - 7723 View in Reaxys

97 % Turnov.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, trichloroisocyanuric acid in dichloromethane, Time= 6h, T= 20 °C De Luca, Lidia; Giacomelli, Giampaolo; Porcheddu, Andrea; Organic Letters; vol. 3; nb. 19; (2001); p. 3041 - 3043 View in Reaxys

100 % Chromat.

With iodosylbenzene, potassium bromide in water, Time= 4h, sonication

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Tohma, Hirofumi; Maegawa, Tomohiro; Takizawa, Shinobu; Kita, Yasuyuki; Advanced Synthesis and Catalysis; vol. 344; nb. 3-4; (2002); p. 328 - 337 View in Reaxys With oxygen, sodium acetate, (neocuproine)Pd(OAc)2 in water, dimethyl sulfoxide, Time= 3h, T= 100 °C , p= 37503.8Torr Ten Brink, Gerd-Jan; Arends, Isabel W. C. E.; Hoogenraad, Marcel; Verspui, Goeran; Sheldon, Roger A.; Advanced Synthesis and Catalysis; vol. 345; nb. 12; (2003); p. 1341 - 1352 View in Reaxys With trimethylaluminum in toluene, Time= 1h, T= 20 °C , Oppenauer oxidation Graves, Christopher R.; Zeng, Bi-Shun; Nguyen, SonBinh T.; Journal of the American Chemical Society; vol. 128; nb. 39; (2006); p. 12596 - 12597 View in Reaxys 98 % Spectr.

With N,N,N',N'-tetramethylguanidine in (2)H8-toluene, Time= 3h, T= 20 °C Matano, Yoshihiro; Suzuki, Takeshi; Shinokura, Tomonori; Imahori, Hiroshi; Tetrahedron Letters; vol. 48; nb. 16; (2007); p. 2885 - 2888 View in Reaxys With (R,R)-1,2-diphenylethylenediamine, potassium tert-butylate, cyclohexanone, [(η6-C6H6)Ru(μ-Cl)Cl]2, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in tetrahydrofuran, Time= 20h, T= 60 °C Adair, Gareth R. A.; Williams, Jonathan M. J.; Chemical Communications; nb. 25; (2007); p. 2608 - 2609 View in Reaxys With ketoreductase, acetone in phosphate buffer, pentane, T= 24.99 °C , pH= 7.3, Equilibrium constant, Further Variations: Solvents Tewari, Yadu B.; Kishore, Nand; Rozzell, J. David; Vanderah, David J.; Schantz, Michele M.; Journal of Chemical Thermodynamics; vol. 38; nb. 10; (2006); p. 1165 - 1171 View in Reaxys

95 % Spectr.

With oxygen, sodium acetate, bis(dibenzylideneacetone)-palladium(0) in toluene, Time= 24h, T= 85 °C , p= 760.051Torr Yang, Min; Yip, Kai-Tai; Pan, Jie-Hui; Chen, Ying-Chun; Zhu, Nian-Yong; Yang, Dan; Synlett; nb. 18; (2006); p. 3057 3060 View in Reaxys

100 % Chromat.

With tetrabutylammomium bromide, oxygen, sodium nitrite, SBA-15-supported TEMPO in acetic acid, Time= 3h, T= 50 °C , p= 760.051Torr Karimi, Babak; Biglari, Abbass; Clark, James H.; Budarin, Vitaly; Angewandte Chemie - International Edition; vol. 46; nb. 38; (2007); p. 7210 - 7213 View in Reaxys With dihydrogen peroxide, [dimethyl dioctadecylammonium]9[EuW10O36], Time= 5h, T= 80 °C Gao, Jinbo; Zhang, Yongna; Jia, Guoqing; Jiang, Zongxuan; Wang, Shouguo; Lu, Hongying; Song, Bo; Li, Can; Chemical Communications; nb. 3; (2008); p. 332 - 334 View in Reaxys

99 %Spectr. With tris(4-chlorophenyl)mesitylbismuthonium tetrafluoroborate, N,N,N',N'-tetramethylguanidine in chloroform-d1, Time= 1h, T= 20 °C Matano, Yoshihiro; Suzuki, Takeshi; Iwata, Takaharu; Shinokura, Tomonori; Imahori, Hiroshi; Bulletin of the Chemical Society of Japan; vol. 81; nb. 12; (2008); p. 1621 - 1628 View in Reaxys With Sphingobium yanoikuyae alcohol dehydrogenase, NADP in water, Enzymatic reaction, Kinetics Lavandera, Ivan; Kern, Alexander; Resch, Verena; Ferreira-Silva, Bianca; Glieder, Anton; Fabian, Walter M. F.; De Wildeman, Stefaan; Kroutil, Wolfgang; Organic Letters; vol. 10; nb. 11; (2008); p. 2155 - 2158 View in Reaxys

26/332

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55 %Chromat.

With NADP, chloroacetone, Time= 24h, T= 30 °C , pH= 7.5, Microbiological reaction, aq. buffer Lavandera, Ivan; Kern, Alexander; Resch, Verena; Ferreira-Silva, Bianca; Glieder, Anton; Fabian, Walter M. F.; De Wildeman, Stefaan; Kroutil, Wolfgang; Organic Letters; vol. 10; nb. 11; (2008); p. 2155 - 2158 View in Reaxys

93 %Chromat.

With 2,2'-azobis(isobutyronitrile), oxygen in acetonitrile, Time= 7h, T= 100 °C , p= 2584.17Torr , Autoclave Bordoloi, Ankur; Sahoo, Suman; Lefebvre; Halligudi; Journal of Catalysis; vol. 259; nb. 2; (2008); p. 232 - 239 View in Reaxys With dihydrogen peroxide in water, Time= 12h, T= 75 °C , chemoselective reaction Zhang, Yugen; Riduan, Siti Nurhanna; Ying, Jackie Y.; Chemistry - A European Journal; vol. 15; nb. 5; (2009); p. 1077 1081 View in Reaxys

85 %Chromat.

With Candida antarctica lipase B immobilized, dihydrogen peroxide in water, Time= 8h, T= 60 °C , Ionic liquid, Enzymatic reaction, chemoselective reaction Sharma, Upendra K.; Sharma, Nandini; Kumar, Rakesh; Kumar, Rajesh; Sinha, Arun K.; Organic Letters; vol. 11; nb. 21; (2009); p. 4846 - 4848 View in Reaxys

89 %Chromat.

With sodium hypochlorite, potassium bromide in dichloromethane, Cyclooctan, water, Time= 0.08h, pH= 9.1, Flow microreactor, Cooling with ice Bogdan, Andrew; McQuade, D. Tyler; Beilstein Journal of Organic Chemistry; vol. 5; (2009); Art.No: A17 View in Reaxys

97 %Chromat.

With oxygen, potassium carbonate in η,η,η-trifluorotoluene, Time= 2.5h, T= 80 °C , p= 760.051Torr Karimi, Babak; Zamani, Asghar; Abedi, Sedigheh; Clark, James H.; Green Chemistry; vol. 11; nb. 1; (2009); p. 109 - 119 View in Reaxys With oxygen in water, Time= 20h, T= 80 °C , p= 760.051Torr Maity, Prasenjit; Gopinath, Chinnakonda S.; Bhaduri, Sumit; Lahiri, Goutam Kumar; Green Chemistry; vol. 11; nb. 4; (2009); p. 554 - 561 View in Reaxys Stage 1: With gold on titanium oxide in water, Time= 0.166667h, T= 90 °C , Inert atmosphere Stage 2: With dihydrogen peroxide in water, Time= 1.08333h, T= 90 °C , Inert atmosphere, chemoselective reaction Ni, Ji; Yu, Wen-Jian; He, Lin; Sun, Hao; Cao, Yong; He, He-Yong; Fan, Kang-Nian; Green Chemistry; vol. 11; nb. 6; (2009); p. 756 - 759 View in Reaxys With NBu4[O2V(O2CC2H2Ph)2], oxygen in acetonitrile, Time= 1h, T= 80 °C , Inert atmosphere, Molecular sieve Ohde, Christian; Limberg, Christian; Chemistry - A European Journal; vol. 16; nb. 23; (2010); p. 6892 - 6899 View in Reaxys With sodium dichromate, sulfuric acid in dimethyl sulfoxide Chang, Lu; Kuang, Yulong; Qin, Bo; Zhou, Xin; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Organic Letters; vol. 12; nb. 10; (2010); p. 2214 - 2217 View in Reaxys

84 %Chromat.

With tert.-butylhydroperoxide, Cu2(μ-O2CC6H5)4(4-Etpy)2 in methanol, water, Time= 4h, T= 65 °C Sarmah, Purabi; Das, Birinchi K.; Phukan, Prodeep; Catalysis Communications; vol. 11; nb. 10; (2010); p. 932 - 935 View in Reaxys With oxygen in water, Time= 10h, T= 50 °C

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Ma, Zhancheng; Yang, Hengquan; Qin, Yong; Hao, Yajuan; Li, Guang; Journal of Molecular Catalysis A: Chemical; vol. 331; nb. 1-2; (2010); p. 78 - 85 View in Reaxys With Oxone, C26H20N2O3V, tetrabutylammomium bromide in dichloromethane, water, Time= 0.0833333h, T= 20 °C Bagherzadeh, Mojtaba; Amini, Mojtaba; Journal of Coordination Chemistry; vol. 63; nb. 21; (2010); p. 3849 - 3858 View in Reaxys With dihydrogen peroxide, acetic acid, sodium bromide in water, Time= 4h, T= 60 °C Qi, Xingyi; Wang, Jing; Zheng, Liwei; Qi, Lin; Synlett; nb. 4; (2011); p. 555 - 558; Art.No: W17410ST View in Reaxys 93 %Chromat.

With ammonium cerium (IV) nitrate, lithium bromide in water, acetonitrile, Time= 5h, T= 65 °C Nikishin; Sokova; Kapustina; Russian Chemical Bulletin; vol. 59; nb. 2; (2010); p. 391 - 395 View in Reaxys

91 %Chromat.

With tert.-butylnitrite, oxygen in acetic acid, Time= 6h, T= 40 °C , chemoselective reaction Karimi, Babak; Badreh, Ebrahim; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4194 - 4198 View in Reaxys

89 %Chromat.

With tert.-butylnitrite, oxygen in water, Time= 14h, T= 50 °C , p= 760.051Torr Karimi, Babak; Farhangi, Elham; Chemistry - A European Journal; vol. 17; nb. 22; (2011); p. 6056 - 6060 View in Reaxys With boron trifluoride diethyl etherate in dichloromethane, Time= 12h Chen, Jiang-Min; Zeng, Xiao-Mei; Middleton, Kyle; Yusubov, Mekhman S.; Zhdankin, Viktor V.; Synlett; nb. 11; (2011); p. 1613 - 1617 View in Reaxys 2.4. Catalytic oxidation experiments General procedure: The reactions were carried out in a stainless steel reactor equipped with a magnetic stirrer. In a typical run, a mixture of the substrate (1.0 mmol), toluene (5 mL), and the catalyst (0.02-0.2 g; ca. 0.45-4.5 wt.percent; Ru: 0.28-2.80 molpercent) was transferred in the reactor. The reactor was pressurized with oxygen to the total pressure of 10 atm and placed in an oil bath; then, the solution was intensively stirred at 80-120 °C for the reported time. The reactions were followed by gas chromatography (GC) (Shimadzu 17 instrument, Carbowax 20 M capillary column). To take the aliquots for the GC analysis at appropriate time intervals, stirring was stopped and the catalyst was quickly settled by the application of an external permanent magnet. The structures of the products were confirmed by GC/MS (Shimadzu QP2010-PLUS instrument, 70 eV). With oxygen in toluene, Time= 7h, T= 80 °C , p= 7600.51Torr , chemoselective reaction Costa, Vinicius V.; Jacinto, Marcos J.; Rossi, Liane M.; Landers, Richard; Gusevskaya, Elena V.; Journal of Catalysis; vol. 282; nb. 1; (2011); p. 209 - 214 View in Reaxys

98 %Spectr. With Br(1-)*C20H27BrN5O2Pd(1+), oxygen, sodium acetate, Time= 48h, T= 20 - 120 °C Urgoitia, Garazi; Sanmartin, Raul; Herrero, Maria Teresa; Dominguez, Esther; Green Chemistry; vol. 13; nb. 8; (2011); p. 2161 - 2166 View in Reaxys 83 %Chromat.

With Oxone, [Mn(2,4,6-tri-(2-pyridyl)-1,3,5-triazine)Cl2(H2O)]*H2O, tetrabutylammomium bromide in dichloromethane, water, Time= 0.0833333h, T= 20 °C Najafpour, Mohammad Mahdi; Amini, Mojtaba; Bagherzadeh, Mojtaba; Boghaei, Davar M.; McKee, Vickie; Transition Metal Chemistry; vol. 35; nb. 3; (2010); p. 297 - 303 View in Reaxys

> 99 %Chromat.

With oxygen, potassium carbonate in η,η,η-trifluorotoluene, Time= 4h, T= 95 °C Karimi, Babak; Elhamifar, Dawood; Clark, James H.; Hunt, Andrew J.; Organic and Biomolecular Chemistry; vol. 9; nb. 21; (2011); p. 7420 - 7426

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View in Reaxys 35 %Chromat.

With dihydrogen peroxide in water, Time= 72h, T= 37 °C , Ionic liquid, Enzymatic reaction, chemoselective reaction Sharma, Nandini; Sharma, Upendra K.; Salwan, Richa; Kasana, Ramesh C.; Sinha, Arun K.; Catalysis Letters; vol. 141; nb. 4; (2011); p. 616 - 622 View in Reaxys With copper(ll) sulfate pentahydrate, sulfuric acid, dihydrogen peroxide in water, Time= 3h, T= 100 °C Ahmad, Jahir Uddin; Raeisaenen, Minna T.; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 411-412; (2012); p. 180 - 187 View in Reaxys With dihydrogen peroxide, sodium bromide in ethanol, Time= 8h, T= 70 °C Qi, Lin; Qi, Xingyi; Wang, Jing; Zheng, Liwei; Catalysis Communications; vol. 16; nb. 1; (2011); p. 225 - 228 View in Reaxys

100 %Chro- With oxygen, caesium carbonate in toluene, Time= 2.5h, T= 20 °C mat. Karimi, Babak; Esfahani, Farhad Kabiri; Advanced Synthesis and Catalysis; vol. 354; nb. 7; (2012); p. 1319 - 1326 View in Reaxys 32 %Chromat.

Representative procedure for the electrochemical selective oxidation of benzyl alcohol General procedure: A solution of benzyl alcohol (Table 1, entry 1) {1.08 g 10 mmol} in 20 ml chloroform was taken in a beaker type undivided cell. To the above solution a 0.83percent sodium nitrate solution containing 2 ml of HCl (36.5percent solution) was added. The carbon anode (15 cm2) and stainless steel cathode (15 cm2) were placed in the upper aqueous phase. The organic phase alone was stirred with a magnetic stirrer at a rate of 50 rpm in such a way that the organic phase does not touch the electrodes. The electrolysis was conducted galvanostatically at a current density of 50 mA/cm2 until the quantity of charge indicated in Table 1 was passed. The electrolysis was monitored by HPLC (Shimadzu) using a shimpack ODS-18 column (250 mm .x. 4.6 mm) as the stationary phase. The eluent consisted of acetonitrile/water (80:20) at a flow rate of 1 ml/min. Samples including authentic samples were analyzed using UV detector at a wavelength of 254 nm. After completion of electrolysis, the organic phase was separated, washed with water (2 .x. 25 ml), dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to afford 1.13 g of crude benzaldehyde. The HPLC analysis of the residue showed 95percent purity. With hydrogenchloride, sodium nitrate in chloroform, water, Electrochemical reaction Christopher; Lawrence; Anbu Kulandainathan; Kulangiappar; Easu Raja; Xavier; Raja; Tetrahedron Letters; vol. 53; nb. 23; (2012); p. 2802 - 2804 View in Reaxys

> 99 %Chromat.

With oxygen, potassium carbonate in water, Time= 15h, T= 40 °C Karimi, Babak; Behzadnia, Hesam; Bostina, Mihnea; Vali, Hojatollah; Chemistry - A European Journal; vol. 18; nb. 28; (2012); p. 8634 - 8640 View in Reaxys With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate, Reflux Hu, Bin; Meng, Meng; Jiang, Shanshan; Deng, Weiping; Chinese Journal of Chemistry; vol. 30; nb. 6; (2012); p. 1289 - 1294 View in Reaxys

97 %Chromat.

2.3. Catalytic oxidation experiments General procedure:The reactions were carried out in a stainless steel reactor equipped with a magnetic stirrer. In a typical run, a mixture of the substrate (0.4-1.2 mmol), solvent (if any) (2 mL), and the catalyst (10-40 mg; ca. 0.6-2.4 wt.percent; Au: 0.01-0.75 molpercent) was transferred in the reactor. The reactor was pressurized with oxygen to the total pressure of 10 atm and placed in an oil bath; then, the solution was intensively stirred at 80-130 °C for the reported time. The reactions were followed by gas chromatography (GC) (Shimadzu 17 instrument, Carbowax 20 M capillary column). At appropriate time intervals, stirring was stopped and after catalyst settling aliquots were taken and analyzed by GC. To ensure correct GC results in solvent-free reactions and in those with high initial substrate concentrations, the aliquots were diluted with methanol before the analysis. The structures of the products were confirmed by GC/MS (Shimadzu QP2010-PLUS instrument, 70 eV). With oxygen in methanol, Time= 2h, T= 130 °C , p= 7600.51Torr , Stainless steel reactor, chemoselective reaction

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Costa, Vinicius V.; Estrada, Miguel; Demidova, Yulia; Prosvirin, Igor; Kriventsov, Vladimir; Cotta, Rafaela F.; Fuentes, Sergio; Simakov, Andrey; Gusevskaya, Elena V.; Journal of Catalysis; vol. 292; (2012); p. 148 - 156 View in Reaxys 91 %Chromat.

With oxygen, Time= 6.5h, T= 70 °C , p= 760.051Torr Karimi, Babak; Elhamifar, Dawood; Yari, Omolbanin; Khorasani, Mojtaba; Vali, Hojatollah; Clark, James H.; Hunt, Andrew J.; Chemistry - A European Journal; vol. 18; nb. 42; (2012); p. 13520 - 13530 View in Reaxys

73 %Chromat.

With oxygen, sodium carbonate in water, Time= 24h, T= 100 °C , p= 760.051Torr , Green chemistry Osako, Takao; Uozumi, Yasuhiro; Chemistry Letters; vol. 38; nb. 9; (2009); p. 902 - 903 View in Reaxys 3.6 Catalytic activity of the [LAphCuCl]2 complex for the oxidation of alcohols General procedure: The oxidation was carried out in an oxygen atmosphere at room temperature. In a typical experiment, alcohol (1 mmol), [LAphCuCl]2 (0.024 g, 5 molpercent) and Cs2CO3 (0.650 g, 2 mmol) in 5 ml of air (oxygen) saturated toluene were taken in a 15-ml two-necked round-bottom flask which was equipped with an air or oxygen balloon. The solution was magnetically stirred for some hours and the mixture was filtered through a plug of silica, then diluted with toluene (2 ml). The progress of the reaction was monitored by gas chromatography. In a separate blank test, a 15-ml two-necked round-bottom flask was charged with a solution of copper(II) chloride or the ligand in a mixed medium of Cs2CO3 (0.650 g, 2 mmol) in 5 ml of air (oxygen) saturated toluene. Then the flask was equipped with an oxygen balloon. The progress of the reaction was monitored by gas chromatography. With oxygen, caesium carbonate in toluene, Time= 8h, T= 20 °C Balaghi, S. Esmael; Safaei, Elham; Rafiee, Mohammad; Kowsari, Mohammad Hossein; Polyhedron; vol. 47; nb. 1; (2012); p. 94 - 103 View in Reaxys

97 %Chromat.

With dmap, palladium(II) pentavalerate, Trimethylacetic acid in toluene, Time= 24h, T= 100 °C , p= 760.051Torr , Reagent/ catalyst, Concentration, Time, Temperature John, Lukas C.; Gunay, Ahmet; Wood, Andrew J.; Emmert, Marion H.; Tetrahedron; vol. 69; nb. 27-28; (2013); p. 5758 5764 View in Reaxys With [ruthenium(II)(η6-benzene)(chloride)(NC5H4CH2SeC6H5)](hexafluorophosphate), 4-methylmorpholine N-oxide in dichloromethane, Time= 2h, Reflux, Reagent/catalyst, Time Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham Lal; Singh, Ajai K.; Dalton Transactions; vol. 42; nb. 24; (2013); p. 8736 - 8747 View in Reaxys With C37H47CuN2O4*C2H3N, oxygen, caesium carbonate in toluene, Time= 6h, T= 24.84 °C , Catalytic behavior, Reagent/catalyst, Temperature Balaghi, S. Esmael; Safaei, Elham; Chiang, Linus; Wong, Edwin W. Y.; Savard, Didier; Clarke, Ryan M.; Storr, Tim; Dalton Transactions; vol. 42; nb. 19; (2013); p. 6829 - 6839 View in Reaxys With oxygen in toluene, Time= 24h, T= 79.84 °C , p= 759.826Torr Muratsugu, Satoshi; Lim, Min Hwee; Itoh, Takahiro; Thumrongpatanaraks, Wipavee; Kondo, Mio; Masaoka, Shigeyuki; Andy Hor; Tada, Mizuki; Dalton Transactions; vol. 42; nb. 35; (2013); p. 12611 - 12619 View in Reaxys 2.3. Procedure for the catalytic oxidation of benzyl alcohol in acetone General procedure: A 50 mL three-necked glass flask was charged with a mixture ofDPPH (98.6 mmg, 0.25 mmol),WO3/Al2O3 (0.844 g,W: 3 mmol), alcohol(50 mmol), and 30 mL acetone. One neck was connected with awater condenser to reflux. Besides, there must be a deflated balloonon the top of the condenser to collect the evaporated acetone. And anotherneck was connected with a dropping funnel to add acetone.Then an oxygen steel cylinder was used to slowly provide the oxygenfor the reaction through the third neck with an air duct. The ventilationspeed must be adjusted according to the size of the balloon. Moreover,to maintain the airtightness of the whole reaction, the liquid level inthe dropping funnel should be kept in a certain height. Then

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themixturewas stirred at 80 °C for 4 h. The reaction mixture was subjected to GCanalysis to supervise the reaction process till the oxidation ended. With 2,2-diphenyl-1-picrylhydrazyl, tungusten oxide/alumina, oxygen in acetone, Time= 2h, T= 80 °C Zhu, Yaoqin; Xu, Jian; Lu, Ming; Catalysis Communications; vol. 48; (2014); p. 78 - 84 View in Reaxys With C24H29ClIrSe2 (1+)*F6P(1-), potassium carbonate, acetone in water, Time= 7h, T= 80 °C , Oppenauer Oxidation, Catalytic behavior, Reagent/catalyst Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham L.; Singh, Ajai K.; Organometallics; vol. 33; nb. 4; (2014); p. 983 - 993 View in Reaxys With 1-acetoxy-5-nitro-1H-1η3-benzo[d][1,2]iodoxol-3-one in N,N-dimethyl-formamide, Time= 24h, T= 60 °C Iinuma, Masataka; Moriyama, Katsuhiko; Togo, Hideo; European Journal of Organic Chemistry; vol. 2014; nb. 4; (2014); p. 772 - 780 View in Reaxys 98 %Chromat.

Typical oxidation of alcohols General procedure: Into a reaction vessel with a reflux condenser were placed Pd-pol (23.1 mg, Pdpercentw = 2.3), benzyl alcohol (108.1 mg, 1.0 mmol), K2CO3 (138.2 mg, 1.0 mmol) and water (5 mL). The resulting mixture was stirred at 100°C under 1 atm of air. After 6 h, the mixture was cooled down to room temperature and the organic product was extracted with ethyl acetate (3 mL). The water phase was washed with ethyl acetate (2×5 mL) and the organic layers were collected. GLC analysis of the ethyl acetate solution using biphenyl as an internal standard gave a 98percent yield of benzyl aldehyde with >99percent selectivity. With potassium carbonate in water, Time= 16h, T= 100 °C , p= 760.051Torr Dell'Anna, Maria Michela; Mali, Matilda; Mastrorilli, Piero; Cotugno, Pietro; Monopoli, Antonio; Journal of Molecular Catalysis A: Chemical; vol. 386; (2014); p. 114 - 119 View in Reaxys With tert.-butylhydroperoxide, F6P(1-)*C25H28ClN4Ru(1+) in water, Time= 3h, T= 20 °C , Green chemistry, Reagent/catalyst Bolje, Aljosa; Hohloch, Stephan; Urankar, Damijana; Pevec, Andrej; Gazvoda, Martin; Sarkar, Biprajit; Kosmrlj, Janez; Organometallics; vol. 33; nb. 10; (2014); p. 2588 - 2598 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 72h, T= 50 °C Shi, Lei; Wang, Yizhan; Li, Bao; Wu, Lixin; Dalton Transactions; vol. 43; nb. 24; (2014); p. 9177 - 9188 View in Reaxys

99 %Chromat.

Typical procedure for oxidation of alcohols by H2O2 General procedure: In a 25 mL round-bottomed flask equipped with a reflux condenser, a mixture of 1 g PWM/SiO2(M = Cr, Mn, Fe, Co, Ni, and Cu)catalyst containing 0.03 mmol POM, 3 mL acetonitrile and 1 mmol of alcohol was added. Then 1 mL of H2O2 30percent was added and the mixture was refluxed for 2 h with stirring. The progress of the reaction was monitored by GC equipped with a flame ionization detector and a silica pack column. At the end of reaction, the catalyst was filtered out and 10 mL NaHCO3 10percent was added. The organic phase extracted with chloroform and dried. Flash chromatography on a short column of silica gel with ethyl acetate:n-hexane as eluent gave pure products. With dihydrogen peroxide in water, acetonitrile, Time= 2.5h, Reflux Farsani, Mostafa Riahi; Yadollahi, Bahram; Journal of Molecular Catalysis A: Chemical; vol. 392; (2014); p. 8 - 15 View in Reaxys

88 %Spectr. General procedure for the oxidation General procedure: DMSO (2 mmol) in DCM was added to a solution of MeSiCl3 (0.5 mmol) in DCM at – 20 °C, after 3 h, low the temperature to – 78 °C, the color of the solution turned milky white, 1 equivalent of alcohol in DCM was slowly added, after being stirred for 3 h, 8 equivalents of Et3N was slowly added, then the reaction mixture was warmed to the room temperature and diluted by DCM, and then the organic solvents was evaporated. The residue was purified by flash chromatography (elution

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with petroleum ether 30 °C – 60 °C/diethyl ether), with dibromomethane or benzyl methyl ether as internal standard for 1HNMR yield. Stage 1: With Methyltrichlorosilane, dimethyl sulfoxide in dichloromethane, Time= 3h, T= -78 °C , Swern Oxidation Stage 2: With triethylamine in dichloromethane, T= -78 - 20 °C , Swern Oxidation, Temperature Wang, Yuanxun; Wang, Chao; Sun, Jian; Synthetic Communications; vol. 44; nb. 20; (2014); p. 2961 - 2965 View in Reaxys 73 %Chromat.

General procedure for oxidation of alcohols to the correspondingcarbonyl compound with 30percent H2O2 General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5 mmol) were added to an equal mixture of water and acetonitrile (1.5 ml). Then, WO4PMO-IL (0.23 g, ~1.5 mol percent) was added to the above solution and the resulting mixture was stirred at 90 °C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (310 ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. With dihydrogen peroxide in water, acetonitrile, Time= 15h, T= 90 °C , Green chemistry Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; nb. 36; (2014); p. 6114 - 6119 View in Reaxys With C27H29CuN3O2, oxygen, potassium hydroxide in acetonitrile, Time= 18h, T= 20 °C , p= 750.075Torr Alaji, Zahra; Safaei, Elham; Chiang, Linus; Clarke, Ryan M.; Mu, Changhua; Storr, Tim; European Journal of Inorganic Chemistry; vol. 2014; nb. 35; (2014); p. 6066 - 6074 View in Reaxys

83 %Chromat.

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], sodium acetate in water, acetic acid, toluene, Time= 24h, T= 100 °C , Mechanism, Reagent/catalyst, Solvent, Time Gunay, Ahmet; Mantell, Mark A.; Field, Kathleen D.; Wu, Wenbo; Chin, Michael; Emmert, Marion H.; Catalysis Science and Technology; vol. 5; nb. 2; (2015); p. 1198 - 1205 View in Reaxys

73 %Chromat.

4.5 General procedure for oxidation of alcohols to the corresponding carbonyl compound with 30percent H2O2 General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5mmol) were added to an equal mixture of water and acetonitrile (1.5ml). Then, WO4 =PMO-IL (0.23g, η1.5 molpercent) was added to the above solution and the resulting mixture was stirred at 90°C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (3×10ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. With dihydrogen peroxide in water, acetonitrile, Time= 15h, T= 90 °C , Green chemistry, chemoselective reaction Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; vol. 70; nb. 36; (2014); p. 6114 - 6119 View in Reaxys

86 %Chromat.

2.3 Catalytic test General procedure: A certain amount of catalysts (30mg) was placedin the two necked, round-bottomed flask and then1 mmol of alcohol and 10mL of solvent (acetonitrile,dichloromethane and ethanol) were introduced into thereactor through a septum. The catalytic experimentswere carried out under reflux and microwave conditionunder atmospheric pressure and magnetic stirring,using t-BHP 70percent, (0.3–0.5mL) or hydrogen peroxide30percent (0.3 mL) as oxidant. The progress of the reactionwas followed using thin layer chromatography. Afterthe reaction was run for the desired time, the productswere filtered out from the catalyst and then oxidationproducts were analyzed using a gas chromatograph witha GC capillary column HP 6890 and a FID detector.

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With tert.-butylhydroperoxide in acetonitrile, Time= 0.5h, T= 80 °C , p= 760.051Torr Shojaei, A. Fallah; Tabatabaeian; Zanjanchi; Moafi, H. Fallah; Modirpanah; Journal of Chemical Sciences; vol. 127; nb. 3; (2015); p. 481 - 491 View in Reaxys With potassium carbonate in toluene, Time= 16h, T= 85 - 90 °C , p= 760.051Torr , Schlenk technique, Inert atmosphere, Sonication, Green chemistry Wang, Dong; Deraedt, Christophe; Salmon, Lionel; Labrugère, Christine; Etienne, Laetitia; Ruiz, Jaime; Astruc, Didier; Chemistry - A European Journal; vol. 21; nb. 17; (2015); p. 6501 - 6510 View in Reaxys 96 %Chromat.

Typical procedure for catalytic oxidation of alcohols General procedure: The catalytic reactions were carried out in a 10-mL roundbottomflask equipped with a magnetic stirring bar and areflux condenser. The Co-STPOM catalyst (0.001 mmol),water (3 mL), alcohol (1 mmol), and H2O2 (9.8 mmol)were charged in the reaction vessel. The reaction was carriedout at reflux and progress of the reaction was detectedby TLC and GC. After completion of the reaction, organicproduct was isolated by ethyl acetate (3 × 2 mL) and theorganic layer was analyzed by gas chromatography or 1HNMR. Products were assigned by comparing experimentaldata with authentic samples. With 10Na(1+)*4Co(2+)*2O34PW9 (9-), dihydrogen peroxide in water, Time= 3h, Reflux, Green chemistry Farsani, Mostafa Riahi; Assady, Elham; Jalilian, Fariba; Yadollahi, Bahram; Rudbari, Hadi Amiri; Journal of the Iranian Chemical Society; vol. 12; nb. 7; (2015); p. 1207 - 1212; Art.No: 583 View in Reaxys General procedure of the catalytic reaction General procedure: 1 mmol benzyl alcohol, 1.375 g catalyst, 20 ml water, and15 ml ether were mixed in a flask (50 ml). A balloon wasused to introduce O2 at ambient pressure, keeping the temperatureat 30 °C for a given time. At the end of the reaction,a few drops of diluted HCl solution (1 mol/L) wereadded to the reaction system, and the pH of water wasadjusted to 3–4. After stirring, the catalyst was transferredinto the water and the upper organic layer was isolated forGC analysis. With oxygen in diethyl ether, water, Time= 10h, T= 30 °C , p= 760.051Torr , chemoselective reaction Zhu, Yaoqin; Xu, Jia; Lu, Ming; Journal of the Iranian Chemical Society; vol. 12; nb. 7; (2015); p. 1213 - 1219; Art.No: 584 View in Reaxys 2.3. Catalytic studies General procedure: Liquid phase oxidation of benzyl alcohol was carried out in a batch reactor at atmospheric pressure. In a typical experiment, 0.1 g of the zeolite catalyst (typically, 66MOR(AT-3.0)), 20 mmol benzyl alcohol (BzOH), 25 mmol aqueous tert-butyl hydroperoxide (TBHP) as the oxidant and 10 ml of acetonitrile as the solvent wereplaced in a round-bottom flask equipped with a water condenser and a thermometer. The resulting mixture was kept at 90 °C for 4 h under stirring, and then cooled to room temperature. The oxidized products after the catalytic reaction were separated by centrifugation. The products were analyzed in a gas chromatograph with a flame ionization detector, using a SGE BPX70 capillary column (70percent cyanopropyl polysilphenylene-siloxane, 30 m 0.53 mm 0.50 lm) and N2 as the carrier gas. With tert.-butylhydroperoxide in [(2)H6]acetone, Time= 4h, T= 90 °C , p= 760.051Torr Narayanan; Vijaya, J. Judith; Sivasanker; Alam, Mahboob; Tamizhdurai; Kennedy, L. John; Polyhedron; vol. 89; (2015); p. 289 - 296 View in Reaxys in N,N-dimethyl-formamide, Time= 2h, T= 120 °C , Inert atmosphere Zhu, Yaoqin; Shen, Mengnan; Xia, Yonggen; Lu, Ming; Applied Organometallic Chemistry; vol. 29; nb. 3; (2015); p. 152 156 View in Reaxys With 1-acetoxy-5-nitro-1H-1η3-benzo[d][1,2]iodoxol-3-one in N,N-dimethyl-formamide, Time= 24h, T= 60 °C , Reagent/catalyst Iinuma, Masataka; Moriyama, Katsuhiko; Togo, Hideo; European Journal of Organic Chemistry; vol. 2014; nb. 4; (2014); p. 772 - 780 View in Reaxys

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With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in tert-Amyl alcohol, Time= 6h, Reflux Wang, Rongzhou; Ma, Juan; Li, Feng; Journal of Organic Chemistry; vol. 80; nb. 21; (2015); p. 10769 - 10776 View in Reaxys 97 %Chromat.

With dihydrogen peroxide in acetonitrile, Time= 2.5h, T= 80 °C Naghdi, Zahra; Farzaeli, Razieh; Aliyan, Hamid; Russian Journal of Applied Chemistry; vol. 88; nb. 8; (2015); p. 1343 1350 View in Reaxys Catalytic oxidation General procedure: In a typical experiment an alcohol (1 mmol), salen–Mn(III) complex (0.02 mmol), NBS (0.13 mmol), and CH2Cl2 (2 mL) was loaded into a 5 mL flask at room temperature. NaOCl (2.3 mmol) was added dropwise within 10 min and progress of the reaction was monitored by GC. Upon completion of the process the reaction mixture was treated twice with10 mL of 10percent NaHSO3 solution and the organic phase was dried over anhydrous sodium sulfate and filtered off. The solvent was removed by distillation. The residue was distilled under low pressure. With sodium hypochlorite, N-Bromosuccinimide, <N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato> manganese(III) chloride in dichloromethane, water, Time= 0.17h, T= 25 °C , chemoselective reaction Zhang; Lü; Cui; Zhao; Russian Journal of General Chemistry; vol. 84; nb. 10; (2014); p. 2021 - 2026; Zh. Obshch. Khim. View in Reaxys

90 %Chromat.

2.4 General procedure for the oxidation of aromatic alcohols General procedure: Alcohols (1 mmol) were added in a two round bottomed glass flask containing a mixture of cobalt chitosan (5 mol percent, 0.023 g) and K2CO3 (0.5 mmol,0.069 g) in 10 mL p-xylene. The flask was fitted with a reflux condenser and mixture was heated at 80°C with continuous bubbling of air with flow rate of 15 mLmin−1. After completion of the reaction (progress of the reaction followed by TLC), catalyst was separated by an external magnet and the reaction mixture was analyzed by gas chromatography using a CP-Sil-8 fused silica capillary column. With potassium carbonate in para-xylene, Time= 1h, T= 80 °C Shaabani, Ahmad; Boroujeni, Mahmoud Borjian; Sangachin, Mona Hamidzad; Journal of Chemical Sciences; vol. 127; nb. 11; (2015); p. 1927 - 1935 View in Reaxys 2.3. Catalytic oxidation of alcohol General procedure: Liquid-phase catalytic oxidation of benzyl alcohol was carriedout in a 25 mL two-neck flask with reflux condenser and magneticallystirred autoclave heated in an oil bath under atmospheric pressure. Dioxygen was bubbled (10 mL/ min) through a solutionof acetonitrile (ACN, 8 mL), benzyl alcohol (108 mg, 1 mmol), IBA (216 mg, 3 mmol), and catalyst (1.9 106 mmol, calculated on the intercalated metlloporphyrin) at 60°C. The product samples were drawn at regular time intervals and analyzed with a gas chromatograph(Shimadzu GC-2010AF) having a Chromopak capillarycolumn and FID detector. The products were further confirmedusing GC–MS (Shimadzu GCMS-2010). The conversions of the reactions were calculated with no allowance for the background. After the reaction, the resulting mixture was cooled and the catalyst was separated by centrifugation and washed with solvent. After drying in vacuum, the recycled catalyst can be reused in the next run under the same conditions. The conversion, yield of benzaldehyde, and selectivity presented here are based on the GC calculations using chlorobenzene as the internal standard reference compound. With oxygen, isobutyraldehyde in acetonitrile, Time= 2.5h, T= 60 °C , p= 760.051Torr , Reflux, Autoclave Zhou, Wei-You; Tian, Peng; Sun, Fu'An; He, Ming-Yang; Chen, Qun; Journal of Catalysis; vol. 335; (2016); p. 105 - 116 View in Reaxys With Pd/TiO2(at)MIL-101, Time= 40h, T= 90 °C , Inert atmosphere Tilgner, Dominic; Friedrich, Martin; Hermannsdörfer, Justus; Kempe, Rhett; ChemCatChem; vol. 7; nb. 23; (2015); p. 3916 - 3922 View in Reaxys 2.4 Catalytic oxidation of alcohols General procedure: In a typical process, into a 5ml two-necked, round-bottom flask equipped with a magnetic stirrer and a thermometer were added the ruthenium complex [Ru(pymieb)(pydic)] (0.002mmol) and the substrate alcohol (2mmol) successively. The mixture was heated to 40°C under stirring. Then t-butyl hydroperoxide (TBHP) was added dropwise to the mixture and the

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temperature was kept at 40°C until completion of the reaction. The reaction samples were analyzed on a Shandong Lunan Ruihong Gas Chromatograph (SP-6800A) equipped with a FID detector and a SE 30 column (30m×0.5mm). The conditions used in gas chromatography were temperature of the detector 280°C, column temperature 130–220°C (varying with alcohols), pressure of the carrier gas 0.05–0.07MPa (varying with alcohols). With tert.-butylhydroperoxide, Ru[2-(2-pyridymethylimino)ethylbenzimidazole]pyridinedicarboxylate in neat (no solvent), Time= 4h, T= 40 °C Zhang, Yuecheng; Liu, Liu; Cao, Xiaohui; Zhao, Jiquan; Polyhedron; vol. 105; (2016); p. 170 - 177 View in Reaxys > 99 %Chromat.

With oxygen in water, Time= 24h, T= 90 °C , p= 759.826Torr , Green chemistry Karimi, Babak; Naderi, Zahra; Khorasani, Mojtaba; Mirzaei, Hamid M.; Vali, Hojatollah; ChemCatChem; vol. 8; nb. 5; (2016); p. 906 - 910 View in Reaxys

87 %Chromat.

With potassium carbonate in water, Time= 17h, T= 100 °C , p= 760.051Torr , Green chemistry Pourjavadi, Ali; Safaie, Niloofar; Hosseini, Seyed Hassan; Bennett, Craig; New Journal of Chemistry; vol. 40; nb. 2; (2016); p. 1729 - 1736 View in Reaxys General procedure for the oxidation reaction General procedure: A mixture of benzyl alcohol (1 mmol), t-BHP 70 percent(0.3 ml) and RuO2(at)ZrO2 4 wtpercent (20 mg) in acetonitrile(5 ml) was stirred magnetically into the reactor through a septum. The progress of the reaction was followed using thin layer chromatography and after completion of the reaction, the products were filtered out from the catalyst.Then, the obtained oxidation products were analyzed using a gas chromatograph with a GC capillary column HP 6890and FID detector. in acetonitrile, Time= 0.116667h, Microwave irradiation, Green chemistry Shojaei, Abdollah Fallah; Tabatabaeian, Khalil; Hamidiyan, Massome; Hejazi, Seyyedeh Zoha; Journal of the Iranian Chemical Society; vol. 13; nb. 5; (2016); p. 803 - 808 View in Reaxys

90 %Chromat.

With porous chitosan–manganese dioxide nanohybrid, air in para-xylene, Time= 1h, T= 80 °C , Green chemistry Shaabani, Ahmad; Borjian Boroujeni, Mahmoud; Laeini, Mohmmad Sadegh; Applied Organometallic Chemistry; vol. 30; nb. 3; (2016); p. 154 - 159 View in Reaxys With Jones reagent in acetone, Time= 0.5h, T= 0 - 20 °C Li, Chengliang; Jin, Tao; Zhang, Xinglu; Li, Chunju; Jia, Xueshun; Li, Jian; Organic Letters; vol. 18; nb. 8; (2016); p. 1916 - 1919 View in Reaxys Typical procedure for catalytic oxidation of alcohols The typical procedure is the following: 3 mL CH3CN,0.01 mmol catalyst, and 1 mmol Benzyl alcohol were added to roundbottomed flask equipped with a reflux condenser.Then, 1 mmol aqueous H2O2 was dropwise added with in 5 min under stirring. The reaction time was counted after the addition of aqueous H2O2, and the reaction mixture was sampled periodically. The typical reaction temperature is 85 °C, and reaction time is 3–7 h. The progress was monitored by TLC (EtOAc/n-hexane, 1/5). After completionof the reaction, the catalyst was separated from the product by filtration and the liquid was analyzed by a gas chromatograph. With dihydrogen peroxide in water, acetonitrile, Time= 3h, T= 85 °C Babahydari, Ali Kazemi; Fareghi-Alamdari, Reza; Hafshejani, Shahrbanou Moradpour; Rudbari, Hadi Amiri; Farsani, Mostafa Riahi; Journal of the Iranian Chemical Society; vol. 13; nb. 8; (2016); p. 1463 - 1470 View in Reaxys

80 %Chromat.

With potassium hydroxide in para-xylene, Time= 5h, T= 80 °C , Green chemistry Shaabani, Ahmad; Shaabani, Shabnam; Afaridoun, Hadi; RSC Advances; vol. 6; nb. 54; (2016); p. 48396 - 48404 View in Reaxys

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93 %Chromat.

With tert.-butylhydroperoxide, Cs5V14As8O42Cl in water, acetone, Time= 48h, T= 20 °C Campbell, McKenzie L.; Sulejmanovic, Dino; Schiller, Jacqueline B.; Turner, Emily M.; Hwu, Shiou-Jyh; Whitehead, Daniel C.; Catalysis Science and Technology; vol. 6; nb. 9; (2016); p. 3208 - 3213 View in Reaxys With oxygen in water, Time= 8h, T= 80 °C , p= 760.051Torr Chen, Lijuan; Feng, Tao; Wang, Pengfei; Chen, Ziwen; Yan, Riqing; Liao, Bo; Xiang, Yujun; Applied Catalysis A: General; vol. 523; (2016); p. 304 - 311 View in Reaxys

85 %Chromat.

With potassium carbonate in para-xylene, Time= 2h, T= 80 °C , Green chemistry Shaabani, Ahmad; Afaridoun, Hadi; Shaabani, Shabnam; Applied Organometallic Chemistry; vol. 30; nb. 9; (2016); p. 772 - 776 View in Reaxys

85 %Chromat.

With potassium hydroxide in para-xylene, Time= 5h, T= 80 °C , Green chemistry Shaabani, Ahmad; Afaridoun, Hadi; Shaabani, Shabnam; Keramati Nejad, Mina; RSC Advances; vol. 6; nb. 99; (2016); p. 97367 - 97375 View in Reaxys With oxygen in ethanol, Time= 16h, T= 80 °C , p= 760.051Torr , Autoclave, Reagent/catalyst Slot, Thierry K.; Eisenberg, David; van Noordenne, Dylan; Jungbacker, Peter; Rothenberg, Gadi; Chemistry - A European Journal; vol. 22; nb. 35; (2016); p. 12307 - 12311 View in Reaxys

99 %Chromat.

With potassium carbonate in water, T= 80 °C , Catalytic behavior Vessally, Esmail; Ghasemisarabbadeih, Mostafa; Ekhteyari, Zeynab; Hosseinzadeh-Khanmiri, Rahim; Ghorbani-Kalhor, Ebrahim; Ejlali, Ladan; RSC Advances; vol. 6; nb. 108; (2016); p. 106769 - 106777 View in Reaxys

99 %Chromat.

With dihydrogen peroxide in water, acetonitrile, Time= 4h, T= 90 °C Zohreh, Nasrin; Tavakolizadeh, Maryam; Hosseini, Seyed Hassan; Jahani, Mahboobeh; Pourjavadi, Ali; Bennett, Craig; New Journal of Chemistry; vol. 40; nb. 12; (2016); p. 10325 - 10332 View in Reaxys

99 %Spectr. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, laccase from Trametes versicolor, oxygen in water, Time= 168h, T= 20 °C , Enzymatic reaction Galletti, Paola; Pori, Matteo; Funiciello, Federica; Soldati, Roberto; Ballardini, Alberto; Giacomini, Daria; ChemSusChem; vol. 7; nb. 9; (2014); p. 2684 - 2689 View in Reaxys 90 %Chromat.

With tert.-butylnitrite, oxygen, acetic acid in toluene, Time= 4h, T= 50 °C , p= 750.075Torr , Reagent/catalyst Karimi, Babak; Farhangi, Elham; Vali, Hojatollah; Vahdati, Saleh; ChemSusChem; vol. 7; nb. 9; (2014); p. 2735 - 2741 View in Reaxys Reaction procedure for benzyl alcohol oxidation General procedure: Liquid-phase catalytic oxidation of benzyl alcohol was carriedout in a 25 mL two-neck-flask with reflux condenser and magnet-ically stirred autoclave heated in an oil bath under atmosphericpressure. Dioxygen was bubbled (10 mL/ min) through a solution oftoluene (8 mL), benzyl alcohol (216 mg, 2 mmol), and catalyst (1.0 g)at 80C. The product samples were drawn at regular time intervalsand analyzed with a gas chromatography (Shimadzu GC-2010AF)having SE-30 capillary column and FID detector. The products werefurther confirmed using GC–MS (Shimadzu GCMS-2010) with a DB-5MS capillary column. After the reaction, the resulting mixture wascooled with ice bath and the catalyst was separated by centrifuga-tion and washed with solvent. After drying at room temperature invacuum, the recycled catalyst can be reused in the next run underthe same conditions. The conversion, yield of benzaldehyde andselectivity presented here are based on the GC calculations usingchlorobenzene as the internal standard reference compound. With oxygen in toluene, Time= 12h, T= 80 °C , p= 760.051Torr , Autoclave, Heating

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Zhou, Weiyou; Tao, Qianyun; Pan, Jiugao; Liu, Jie; Qian, Junfeng; He, Mingyang; Chen, Qun; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 255 - 265 View in Reaxys 2.2 General procedure for the aerobic oxidation ofalcohols using NHPI/O2/CoTPP-Zn2Al-LDH system General procedure: In a typical experiment, a solution of NHPI (0.6 mmol,20 molpercent) and CoTPP-Zn2Al-LDH (0.01 mmol of CoTPP content, 30 mg) in PhCN or CH3CN (10 mL) was prepared in a 25mL round-bottom flask equippedwith magnetic stirrer. To this solution alcohol (3 mmol)was added and the resulting mixture was stirred at100 or 80 °C. Then dioxygen was bubbled through thesolution at a rate of 20mLmin−1. All the productswere identified by GC-MS and quantified at differentintervals during the reaction by GC-FID (ShimadzuGC-2010AF). With N-hydroxyphthalimide, oxygen in benzonitrile, Time= 28h, T= 100 °C , Reagent/catalyst Zhou, Weiyou; Chen, Dongwei; Cui, Aijun; Qian, Junfeng; He, Mingyang; Chen, Qun; Journal of Chemical Sciences; vol. 129; nb. 3; (2017); p. 295 - 299 View in Reaxys With nickel dichloride in water, Time= 6h, T= 20 °C , pH= 9, Inert atmosphere, Irradiation Zhao, Lei-Min; Meng, Qing-Yuan; Fan, Xiang-Bing; Ye, Chen; Li, Xu-Bing; Chen, Bin; Ramamurthy, Vaidhyanathan; Tung, Chen-Ho; Wu, Li-Zhu; Angewandte Chemie - International Edition; vol. 56; nb. 11; (2017); p. 3020 - 3024; Angew. Chem.; vol. 129; nb. 11; (2017); p. 3066 - 3070,5 View in Reaxys With tert.-butylhydroperoxide, Cs11Na3(V15O36)Cl6 in water, acetone, Time= 48h, T= 20 °C , Sealed tube, Reagent/catalyst Campbell, McKenzie L.; Sulejmanovic, Dino; Schiller, Jacqueline B.; Turner, Emily M.; Hwu, Shiou-Jyh; Whitehead, Daniel C.; Helvetica Chimica Acta; vol. 100; nb. 3; (2017) View in Reaxys With water, sodium sulfate, Time= 1h, T= 20 °C , Irradiation, Electrochemical reaction, Green chemistry Zhang, Ruikang; Shao, Mingfei; Li, Zhenhua; Ning, Fanyu; Wei, Min; Evans, David G.; Duan, Xue; Chemistry - A European Journal; vol. 23; nb. 34; (2017); p. 8142 - 8147 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, Trametes versicolor laccase in tert-butyl methyl ether, Time= 16h, T= 30 °C , pH= 5, Enzymatic reaction Martínez-Montero, Lía; Gotor, Vicente; Gotor-Fernández, Vicente; Lavandera, Iván; Green Chemistry; vol. 19; nb. 2; (2017); p. 474 - 480 View in Reaxys 85 %Chromat.

With tert.-butylhydroperoxide in acetonitrile, Time= 0.025h, p= 760.051Torr , Microwave irradiation, Reagent/catalyst, Solvent Shojaei, Abdollah Fallah; Shirini, Farhad; Hedayati, Elaheh; Inorganic and Nano-Metal Chemistry; vol. 47; nb. 9; (2017); p. 1312 - 1317 View in Reaxys

95 %Chromat.

With C66H60Cl2N10P2Ru2 (2+)*2Cl(1-), potassium tert-butylate in toluene, Time= 16h, Reflux, Inert atmosphere, Schlenk technique Wang, Qingfu; Chai, Huining; Yu, Zhengkun; Organometallics; vol. 36; nb. 18; (2017); p. 3638 - 3644 View in Reaxys With [fac-N-(2-(diphenylphosphino)ethyl)-5,6,7,8-tetrahydroquinolin-8-amine]RuCl2(triphenylphosphine), potassium tert-butylate in para-xylene, Time= 24h, Reflux, Inert atmosphere, Catalytic behavior Wang, Zheng; Pan, Bing; Liu, Qingbin; Yue, Erlin; Solan, Gregory A.; Ma, Yanping; Sun, Wen-Hua; Catalysis Science and Technology; vol. 7; nb. 8; (2017); p. 1654 - 1661 View in Reaxys With dihydrogen peroxide in neat (no solvent), Time= 1.25h, T= 80 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent, Temperature Malakooti; Feghhi; New Journal of Chemistry; vol. 41; nb. 9; (2017); p. 3405 - 3413

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View in Reaxys 75 %Spectr. With C30H43ClCoN2P3 (1+)*Cl(1-), potassium tert-butylate in toluene, Time= 48h, T= 125 °C , Sealed tube Xu, Shi; Alhthlol, Latifah M.; Paudel, Keshav; Reinheimer, Eric; Tyer, David L.; Taylor, Daniela K.; Smith, Amberlynn M.; Holzmann, Jonathan; Lozano, Edgar; Ding, Keying; Inorganic Chemistry; vol. 57; nb. 5; (2018); p. 2394 - 2397 View in Reaxys With oxygen in toluene, Time= 4h, T= 80 °C Sun, Fuan; Zhou, Jiacheng; Zhou, Weiyou; Pan, Jiugao; Qian, Junfeng; He, Mingyang; Chen, Qun; New Journal of Chemistry; vol. 42; nb. 6; (2018); p. 4029 - 4035 View in Reaxys > 99 %Spectr.

With 2BF4 (1-)*C21H37IrN2O3 (2+) in toluene, tert-butyl alcohol, Time= 24h, Schlenk technique, Inert atmosphere, Reflux González Miera, Greco; Martínez-Castro, Elisa; Martín-Matute, Belén; Organometallics; vol. 37; nb. 5; (2018); p. 636 644 View in Reaxys O

Rx-ID: 303585 View in Reaxys 2/824 Yield 100 %

Conditions & References With potassium tert-butylate, trimethyl-4,6,9 hexaza-1,3,4,6,7,9 phospha-5 tricyclo<3.3.1.13,7>decane, [(η6-C6H6)Ru(μ-Cl)Cl]2 in tetrahydrofuran, Time= 0.0833333h, T= 75 °C , Product distribution, Further Variations: Catalysts, Solvents Diaz-Alvarez, Alba E.; Crochet, Pascale; Zablocka, Maria; Duhayon, Carine; Cadierno, Victorio; Gimeno, Jose; Majoral, Jean Pierre; Advanced Synthesis and Catalysis; vol. 348; nb. 12-13; (2006); p. 1671 - 1679 View in Reaxys

99 %

With potassium tert-butylate, [RuCl2(η6-p-cymene){η1-(P)-PPh2(OCH2CH2NMe2)}] in tetrahydrofuran, Time= 0.25h, T= 75 °C Crochet, Pascale; Diez, Josefina; Fernandez-Zumel, Mariano A.; Gimeno, Jose; Advanced Synthesis and Catalysis; vol. 348; nb. 1-2; (2006); p. 93 - 100 View in Reaxys

99 %

With [Ru(η3:η3-C10H16)Cl(η2-O,O-CH3CO2)] in aq. phosphate buffer, Time= 2.5h, T= 50 °C , pH= 7, Sealed tube, Inert atmosphere, Reagent/catalyst, chemoselective reaction Ríos-Lombardía, Nicolás; Vidal, Cristian; Liardo, Elisa; Morís, Francisco; García-Álvarez, Joaquín; González-Sabín, Javier; Angewandte Chemie - International Edition; vol. 55; nb. 30; (2016); p. 8691 - 8695; Angew. Chem.; vol. 128; nb. 30; (2016); p. 8833 - 8837,5 View in Reaxys

98 %

With Fe(II)(bis(2-(diisopropylphosphino)ethyl)amine)(CO)(H)(Cl), potassium tert-butylate in toluene, Time= 1h, T= 80 °C , Inert atmosphere Xia, Tian; Wei, Zhihong; Spiegelberg, Brian; Jiao, Haijun; Hinze, Sandra; de Vries, Johannes G.; Chemistry - A European Journal; vol. 24; nb. 16; (2018); p. 4043 - 4049 View in Reaxys

97 %

With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate in toluene, T= 20 °C Bouziane, Asmae; Regnier, Thomas; Carreaux, Francois; Carboni, Bertrand; Bruneau, Christian; Renaud, Jean-Luc; Synlett; nb. 2; (2010); p. 207 - 210 View in Reaxys

95 %

With tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate, potassium carbonate in acetonitrile, Time= 1h, Inert atmosphere, Reflux

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Bouziane, Asmae; Carboni, Bertrand; Bruneau, Christian; Carreaux, Francois; Renaud, Jean-Luc; Tetrahedron; vol. 64; nb. 51; (2008); p. 11745 - 11750 View in Reaxys 95 %

With [RuCl(η5-(3-phenyl)indenyl)(PPh3)2] in toluene, Time= 1h, T= 20 °C Manzini, Simone; Poater, Albert; Nelson, David J.; Cavallo, Luigi; Nolan, Steven P.; Chemical Science; vol. 5; nb. 1; (2013); p. 180 - 188 View in Reaxys

95 %

2.1 General procedure for the catalytic isomerization of allylic alcohols into carbonyl compounds General procedure: The corresponding allylic alcohol (1mmol) and the DES solvent (1g) were introduced into a sealed tube under a nitrogen atmosphere. Complex 1c (0.2–10molpercent) was then introduced at room temperature, and the resulting solution was heated at 75°C for the indicated time. The course of the reaction was monitored by regular sampling and analysis by GC. The validity of this method has been confirmed by analyzing mixtures of the corresponding allylic alcohol/carbonyl compound in known proportions under the same conditions. To evaluate the recyclability of complex 1c, the addition of successive amounts of 1-octen-3-ol to the reaction mixture at regular times was tested. With [Ru(η3:η3-C10H16)Cl2(benzimidazole)] in glycerol, Time= 24h, T= 75 °C , Sealed tube, Inert atmosphere, Green chemistry Vidal, Cristian; Suarez, Francisco J.; Garcia-Alvarez, Joaquin; Catalysis Communications; vol. 44; (2014); p. 76 - 79 View in Reaxys

94 %

With potassium tert-butylate, [Ru(η5-Ph4MeCp)(CO)2Cl] in tetrahydrofuran, toluene, Time= 2.5h, T= 20 °C Martin-Matute, Belen; Bogar, Krisztian; Edin, Michaela; Kaynak, F. Betuel; Baeckvall, Jan-E.; Chemistry - A European Journal; vol. 11; nb. 20; (2005); p. 5832 - 5842 View in Reaxys

92 %

With hydridotris(triphenylphosphine)rhodium in tetrahydrofuran, Heating Uma, Ramalinga; Davies, Maxwell K.; Crevisy, Christophe; Gree, Rene; European Journal of Organic Chemistry; nb. 16; (2001); p. 3141 - 3146 View in Reaxys

92 %

General procedure for the catalytic isomerization of allylic alcohols using complex [RuCl2(η6-C6H6)(PTA-Me)] (3a) General procedure: In a sealed tube, under nitrogen atmosphere, the ruthenium complex [RuCl2( 6-C6H6)(PTA-Me)] (3a) (0.02–0.1 mmol; 0.5–2.5 molpercent of Ru) and K2CO3 (0.05–0.25 mmol; 1.25–6.25 molpercent) were added to a solution of the corresponding allylic alcohol 4a–o (4 mmol) in tetrahydrofuran (4 mL), and the resulting mixture stirred at 75 °C for the indicated time (see Table 4 and Scheme 3). The course of the reaction was monitored by taking regularly samples of ca. 10 L which after dilution with dichloromethane (3 mL) were analyzed by GC. After the reaction was finished, the mixture was cooled to room temperature leading to the partial precipitation of 3a. The solid was separated by filtration and the reaction product isolated by solvent removal and chromatographic workup of the residue on silica-gel using a mixture of EtOAc–hexane (1:10) as eluent. The identity of the resulting carbonyl compounds 5a–o was assessed by comparison of their retention times with those of commercially available pure samples (Sigma–Aldrich or Acros Organics), by their fragmentation in GC/MS, and/or NMR spectroscopy. With C13H21Cl2N3PRu(1+)*Cl(1-), potassium carbonate in tetrahydrofuran, Time= 20h, T= 75 °C , Inert atmosphere, Sealed tube, Catalytic behavior Menendez-Rodriguez, Lucia; Crochet, Pascale; Cadierno, Victorio; Journal of Molecular Catalysis A: Chemical; vol. 366; (2013); p. 390 - 399 View in Reaxys

91 %

With [Ru(η(5)-C5,η-N-Cp(N))(CH3CN)2]PF6 in tetrahydrofuran-d8, Time= 0.8h, T= 60 °C , Inert atmosphere Batuecas, Maria; Esteruelas, Miguel A.; Garcia-Yebra, Cristina; Onate, Enrique; Organometallics; vol. 29; nb. 9; (2010); p. 2166 - 2175 View in Reaxys

90 %

With tetrapropylammonium perruthennate, undecan-2-ol in fluorobenzene, Heating, Isomerization Marko, Istvan E.; Gautier, Arnaud; Tsukazaki, Masao; Llobet, Antoni; Plantalech-Mir, Elena; Urch, Christopher J.; Brown, Stephen M.; Angewandte Chemie - International Edition; vol. 38; nb. 13-14; (1999); p. 1960 - 1962 View in Reaxys

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90 %

With [Ir(OH)(COD)(IiPr)] in toluene, Time= 1h, T= 140 °C , Microwave irradiation, Temperature, Solvent, Reagent/catalyst Nelson, David J.; Fernandez-Salas, Jose A.; Truscott, Byron J.; Nolan, Steven P.; Organic and Biomolecular Chemistry; vol. 12; nb. 34; (2014); p. 6672 - 6676 View in Reaxys

90 %

With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine in toluene, Time= 18h, Sealed tube, Reflux, Reagent/catalyst Martinez-Erro, Samuel; Sanz-Marco, Amparo; Bermejo Gómez, Antonio; Vázquez-Romero, Ana; Ahlquist, Mårten S. G.; Martín-Matute, Belén; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13408 - 13414 View in Reaxys

88%

With tris(triphenylphosphine)ruthenium(II) chloride, sodium acetate, benzaldehyde in 1,2-dichloro-ethane, Time= 4h, T= 90 °C , Schlenk technique, Inert atmosphere Ren, Kai; Hu, Bei; Zhao, Mengmeng; Tu, Yahui; Xie, Xiaomin; Zhang, Zhaoguo; Journal of Organic Chemistry; vol. 79; nb. 5; (2014); p. 2170 - 2177 View in Reaxys

84 %

With iron pentacarbonyl in pentane, Time= 1.5h, UV-irradiation Cherkaoui, Hassan; Soufiaoui, Mohammed; Gree, Rene; Tetrahedron; vol. 57; nb. 12; (2001); p. 2379 - 2383 View in Reaxys

84 %

With 2C25H28N2OP(1-)*2Cl(1-)*2Ru(2+) in tetrahydrofuran, Time= 2h, T= 80 °C , Inert atmosphere, Schlenk technique, Sealed tube Kechaou-Perrot, Manel; Vendier, Laure; Bastin, Stphanie; Sotiropoulos, Jean-Marc; Miqueu, Karinne; Menndez-Rodrguez, Luca; Crochet, Pascale; Cadierno, Victorio; Igau, Alain; Organometallics; vol. 33; nb. 22; (2014); p. 6294 - 6297 View in Reaxys

72 %

With potassium tert-butylate in tetrahydrofuran, T= 20 °C , Schlenk technique, Inert atmosphere Suchand, Basuli; Satyanarayana, Gedu; European Journal of Organic Chemistry; vol. 2017; nb. 26; (2017); p. 3886 - 3895 View in Reaxys

71 %

With sodium hydroxide, di(rhodium)tetracarbonyl dichloride in dichloromethane, T= 25 - 30 °C Alper, Howard; Hachem, Khaled; Journal of Organic Chemistry; vol. 45; nb. 11; (1980); p. 2269 - 2270 View in Reaxys

68 %

With {(η6-p-cymene)RuCl2}{[3-(3,5-diaza-1-azonia-7-phosphatricyclo[3.3.1.13,7]decan-1-yl)propyl]silanetriyltrioxy} supported on silica-coated ferrite nanoparticles in water, Time= 24h, T= 150 °C , p= 5171.62 - 6205.94Torr , Inert atmosphere, Microwave irradiation García-Garrido, Sergio E.; Francos, Javier; Cadierno, Victorio; Basset, Jean-Marie; Polshettiwar, Vivek; ChemSusChem; vol. 4; nb. 1; (2011); p. 104 - 111 View in Reaxys

56 %

With palladium diacetate, p-benzoquinone, lithium tert-butoxide in acetonitrile, Time= 8h, T= 90 °C Chen, Huoji; Huang, Li; Fu, Wei; Liu, Xiaohang; Jiang, Huanfeng; Chemistry - A European Journal; vol. 18; nb. 34; (2012); p. 10497 - 10500 View in Reaxys

40 %

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] in water, acetone, Time= 16h, T= 20 °C , chemoselective reaction Erbing, Elis; Vázquez-Romero, Ana; Bermejo Gómez, Antonio; Platero-Prats, Ana E.; Carson, Fabian; Zou, Xiaodong; Tolstoy, Päivi; Martín-Matute, Belén; Chemistry - A European Journal; vol. 22; nb. 44; (2016); p. 15659 - 15663 View in Reaxys

27 %

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] in tetrahydrofuran, water, Time= 0.5h, T= 75 °C , Catalytic behavior, Time, Reagent/catalyst, Solvent Vázquez-Romero, Ana; Gómez, Antonio Bermejo; Martín-Matute, Belén; ACS Catalysis; vol. 5; nb. 2; (2015); p. 708 - 714 View in Reaxys

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With potassium carbonate Tiffeneau; Bulletin de la Societe Chimique de France; vol. <4> 1; (1907); p. 1212 View in Reaxys With polystyrene-anchored RuCl2(PPh3)3 in 1,3,5-trimethyl-benzene, T= 140 °C , Yield given Zoran, Amikam; Sasson, Yoel; Blum, Jochanan; Journal of Organic Chemistry; vol. 46; nb. 2; (1981); p. 255 - 260 View in Reaxys With polymer-bound RuCl2(PPh3)3 in 1,3,5-trimethyl-benzene, T= 140 °C , other homogeneous and heterogeneous catalysts; rates; Zoran, Amikam; Sasson, Yoel; Blum, Jochanan; Journal of Organic Chemistry; vol. 46; nb. 2; (1981); p. 255 - 260 View in Reaxys 100 % Chromat.

With caesium carbonate, [Ru(η3,η3,η3-C12H18)Cl2], Time= 0.166667h, T= 75 °C Cadierno, Victorio; Garcia-Garrido, Sergio E.; Gimeno, Jose; Chemical Communications; nb. 2; (2004); p. 232 - 233 View in Reaxys

99 % Spectr.

With Cp*RuCl(Ph2P(CH2)2NH2-η2-P,N) in toluene, Time= 1h, T= 30 °C Ito, Masato; Kitahara, Sachiko; Ikariya, Takao; Journal of the American Chemical Society; vol. 127; nb. 17; (2005); p. 6172 - 6173 View in Reaxys

100 % Spectr.

With sodium carbonate, acetone, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt, bis(1,5-cyclooctadiene)diiridium(I) dichloride in water, Time= 1.5h, T= 90 °C Ajjou, Abdelaziz Nait; Pinet, Jean-Louis; Canadian Journal of Chemistry; vol. 83; nb. 6-7; (2005); p. 702 - 710 View in Reaxys

100 % Chromat.

With {Ru(η3:η3-C10H16)(μ-Cl)Cl}2, caesium carbonate, Time= 0.25h, T= 75 °C Cadierno, Victorio; Garcia-Garrido, Sergio E.; Gimeno, Jose; Varela-Alvarez, Adrian; Sordo, Jose A.; Journal of the American Chemical Society; vol. 128; nb. 4; (2006); p. 1360 - 1370 View in Reaxys

94 % Chromat.

With aluminum oxide, Ru(OH)x in toluene, Time= 3h, T= 119.85 °C , p= 760Torr Yamaguchi, Kazuya; Koike, Takeshi; Kotani, Miyuki; Matsushita, Mitsunori; Shinachi, Satoshi; Mizuno, Noritaka; Chemistry - A European Journal; vol. 11; nb. 22; (2005); p. 6574 - 6582 View in Reaxys With H2 activated rhodium-phosphinine complex in 1,4-dioxane, Time= 1h, T= 60 °C Reetz, Manfred T.; Guo, Hongchao; Synlett; nb. 13; (2006); p. 2127 - 2129 View in Reaxys

100 %Spectr.

With tris(triphenylphosphine)ruthenium(II) chloride, Triethoxyvinylsilane in toluene, Time= 2h, T= 140 °C , Inert atmosphere Bartoszewicz, Agnieszka; Martin-Matute, Belen; Organic Letters; vol. 11; nb. 8; (2009); p. 1749 - 1752 View in Reaxys

99 %Chromat.

With [RuCl2(η6-C6H5OCH2CH2OH)(P(OMe)3)], potassium tert-butylate, water, Time= 0.166667h, T= 75 °C Lastra-Barreira, Beatriz; Diez, Josefina; Crochet, Pascale; Green Chemistry; vol. 11; nb. 10; (2009); p. 1681 - 1686 View in Reaxys

> 99 %Spectr.

With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, (1,3,5-triaza-7-phosphaadamantane) in water, Time= 0.0833333h, T= 23 °C , Inert atmosphere, Mechanism, pH-value, Concentration, Reagent/catalyst, Temperature, Time Ahlsten, Nanna; Lundberg, Helena; Martin-Matute, Belen; Green Chemistry; vol. 12; nb. 9; (2010); p. 1628 - 1633 View in Reaxys

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With cis-[Ru(6,6'-Cl2bpy)2(OH2)2](CF3SO3)2, potassium tert-butylate in tetrahydrofuran, Time= 1h, T= 72 °C , Inert atmosphere Liu, Pei Nian; Ju, Kun Dong; Lau, Chak Po; Advanced Synthesis and Catalysis; vol. 353; nb. 2-3; (2011); p. 275 - 280 View in Reaxys > 99 %Chromat.

With [Ru(η3:η3-C10H16)Cl(η2-O,O-CH3CO2)] in water, Time= 0.0833333h, T= 75 °C , Inert atmosphere, Sealed tube, chemoselective reaction Garcia-Alvarez, Joaquin; Gimeno, Jose; Suarez, Francisco J.; Organometallics; vol. 30; nb. 10; (2011); p. 2893 - 2896 View in Reaxys With C40H36Cl2FeN2P2Ru, potassium tert-butylate in tert-butyl alcohol, Time= 2h, T= 120 °C , Inert atmosphere Putignano, Elisabetta; Bossi, Gianluca; Rigo, Pierluigi; Baratta, Walter; Organometallics; vol. 31; nb. 3; (2012); p. 1133 1142 View in Reaxys

89 %Spectr. With Milstein's PNN catalyst in (2)H8-toluene, Time= 24h, Reflux, Inert atmosphere Rigoli, Jared W.; Moyer, Sara A.; Pearce, Simon D.; Schomaker, Jennifer M.; Organic and Biomolecular Chemistry; vol. 10; nb. 9; (2012); p. 1746 - 1749 View in Reaxys > 99 %Chromat.

With C13H18Cl2N2Ru(1+) in water, Time= 1h, T= 75 °C , Inert atmosphere Bellarosa, Luca; Diez, Josefina; Gimeno, Jos; Lledos, Agusti; Suarez, Francisco J.; Ujaque, Gregori; Vicent, Cristian; Chemistry - A European Journal; vol. 18; nb. 25; (2012); p. 7749 - 7765 View in Reaxys

79 %Spectr. With [(η6-p-cymene)RuCl2(Ph2P-(ferrocene-1,1'-diyl)-CONHCH2CH2OH-ηP)], potassium tert-butylate in 1,2-dichloro-ethane, Time= 20h, T= 80 °C , Inert atmosphere, Schlenk technique, Sealed tube, Catalytic behavior, Concentration, Time Schulz, Jiri; Cisarova, Ivana; Stepnicka, Petr; European Journal of Inorganic Chemistry; nb. 31; (2012); p. 5000 - 5010,11 View in Reaxys 83 %Chromat.

With [RuCl{η2N,Nη-C(N-4-C6H4Br)(NiPr)NHiPr}(η6-p-cymene)] in tetrahydrofuran, Time= 12h, T= 80 °C , Inert atmosphere, Sealed tube, Reagent/catalyst, Solvent, Time, Temperature Garcia-Alvarez, Rocio; Suarez, Francisco J.; Diez, Josefina; Crochet, Pascale; Cadierno, Victorio; Antinolo, Antonio; Fernandez-Galan, Rafael; Carrillo-Hermosilla, Fernando; Organometallics; vol. 31; nb. 23; (2012); p. 8301 - 8311 View in Reaxys With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, potassium tert-butylate, lithium chloride, t-butyl [(S)-1-((S)-2-hydroxypropylcarbamoyl)ethyl]carbamate in toluene, Time= 3h, T= 40 °C , Inert atmosphere, Solvent, Reagent/ catalyst Slagbrand, Tove; Lundberg, Helena; Adolfsson, Hans; Chemistry - A European Journal; vol. 20; nb. 49; (2014); p. 16102 16106 View in Reaxys With C17H22Cl2N2Ru, isopropylamine in aq. phosphate buffer, Time= 3h, T= 50 °C , pH= 8.5, Inert atmosphere, Reagent/catalyst, Temperature, Time Ríos-Lombardía, Nicolás; Vidal, Cristian; Cocina, María; Morís, Francisco; García-Álvarez, Joaquín; González-Sabín, Javier; Chemical Communications; vol. 51; nb. 54; (2015); p. 10937 - 10940 View in Reaxys

99 %Chromat.

With [Ru(η3:η3-C10H16)Cl(η2-O,O-CH3CO2)], Time= 0.5h, T= 50 °C , Inert atmosphere, Sealed tube, Green chemistry, Catalytic behavior, Solvent, Temperature Cicco, Luciana; Rodríguez-Álvarez, María J.; Perna, Filippo M.; García-Álvarez, Joaquín; Capriati, Vito; Green Chemistry; vol. 19; nb. 13; (2017); p. 3069 - 3077 View in Reaxys

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94 %Chromat.

With [RuCl{η2-(N,Nη)-hpp}(η3:η3-2,7-dimethylocta-2,6-diene-1,8-diyl)] in water, Time= 1h, T= 80 °C , Inert atmosphere, Sealed tube, Solvent Gámez-Rivera, Sebastián A.; Francos, Javier; Borge, Javier; Cadierno, Victorio; European Journal of Inorganic Chemistry; vol. 2017; nb. 35; (2017); p. 4138 - 4146 View in Reaxys Reaction Steps: 2 1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; Trametes versicolor laccase; oxygen / aq. buffer / 16 h / 30 °C / pH 5 / Enzymatic reaction 2: D-glucose; glucose dehydrogenase-105; NADPH - oxidized form; ene-reductase P1-E01 / aq. buffer / 6 h / 30 °C / Enzymatic reaction With 2,2,6,6-tetramethyl-piperidine-N-oxyl, D-glucose, Trametes versicolor laccase, ene-reductase P1-E01, glucose dehydrogenase-105, oxygen, NADPH - oxidized form in aq. buffer Martínez-Montero, Lía; Gotor, Vicente; Gotor-Fernández, Vicente; Lavandera, Iván; ACS Catalysis; vol. 8; nb. 3; (2018); p. 2413 - 2419 View in Reaxys O

Rx-ID: 551349 View in Reaxys 3/824 Yield 78 %

Conditions & References With aluminium trichloride, Time= 3h, cooling, Friedel-Crafts acylation Xu, Jiaxi; Xia, Jiakun; Lan, Yu; Synthetic Communications; vol. 35; nb. 17; (2005); p. 2347 - 2353 View in Reaxys

78 %

General procedure for the acylation of benzene General procedure: An oven-dried two-necked round bottom flask undernitrogen atmosphere was charged with anhydrous dichloromethane(20 mL) followed by aluminum chloride (4.12 g,30.9 mmol) and benzene 7 (2.90 mL, 34.0 mmol). A solutionof the corresponding acid chloride 8 (30.9 mmol) indichloromethane (10 mL) was then added in a dropwisefashion over a period of an hour and stirring was continuedfor 4 h at room temperature. Upon completion of the reaction,the reaction mixture was poured onto a 15 mL ice-coldsolution of concentrated HCl (3 M) and extracted withdiethyl ether (3 × 10 mL). The combined organic layerswere then washed with brine (10 mL), dried over MgSO4,and concentrated under reduced pressure. The crude productwas then purified by silica gel column chromatographyusing a combination of hexane and ethyl acetate in a 19:1ratio as eluent to afford the corresponding ketone 9. Propiophenone (9a): colorless oil, 78percent (3.23 g); 1HNMR (400 MHz, CDCl3) η: 8.01– 7.90 (m, 2H, Ar), 7.55 (t,J = 7.3 Hz, 1H, Ar), 7.45 (t, J = 7.4 Hz, 2H, Ar), 3.00 (d, J= 7.2 Hz, 2H, H-2), 1.22 (t, J = 7.2 Hz, 3H, H-3); 13C NMR(100 MHz, CDCl3) η: 201.0 (C=O), 136.1 134.0, 128.1,128.0 (Ar), 31.8 (C-2), 7.9 (C-3). The spectroscopic datawere in agreement with the literature report (Liu et al.2014). With aluminum (III) chloride in dichloromethane, Time= 5h, T= 20 °C , Inert atmosphere, Friedel-Crafts Acylation Madumo, Gilbert K.; Moshapo, Paseka T.; Kinfe, Henok H.; Medicinal Chemistry Research; vol. 27; nb. 3; (2018); p. 817 833 View in Reaxys With aluminium trichloride, iron(III) chloride Riddell; Noller; Journal of the American Chemical Society; vol. 54; (1932); p. 290,291, 292 View in Reaxys With carbon disulfide, aluminium trichloride Pampel; Schmidt,G.; Chemische Berichte; vol. 19; (1886); p. 2897 View in Reaxys With aluminium trichloride, T= 50 °C , Zersetzen mit Eis und konz. Salzsaeure Read; Journal of the American Chemical Society; vol. 44; (1922); p. 1753

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View in Reaxys With aluminium trichloride Galewski, Zbigniew; Molecular Crystals and Liquid Crystals (1969-1991); vol. 151; (1987); p. 233 - 242 View in Reaxys With aluminium trichloride in dichloromethane, T= 0 °C , Friedel-Crafts acylation Watanabe, Kazutoshi; Morinaka, Yasuhiro; Hayashi, Yoshio; Shinoda, Masaki; Nishi, Hiroyoshi; Fukushima, Nobuko; Watanabe, Toshiaki; Ishibashi, Akira; Yuki, Satoshi; Tanaka, Masahiko; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 4; (2008); p. 1478 - 1483 View in Reaxys With aluminum (III) chloride Zygadlo; Dardas; Nowicka; Hofmann; Galewski; Molecular Crystals and Liquid Crystals; vol. 509; nb. 1; (2009); p. 283 291 View in Reaxys Friedel-Crafts Acylation Kaczor, Agnieszka Anna; Kronbach, Christiane; Unverferth, Klaus; Pihlaja, Kalevi; Wiinamäki, Kirsti; Sinkkonen, Jari; Kijkowska-Murak, Urszula; Wróbel, Tomasz; Stacha, Tomasz; Matosiuk, Dariusz; Letters in Drug Design and Discovery; vol. 9; nb. 10; (2012); p. 891 - 898 View in Reaxys With aluminum (III) chloride Han, Junru; Li, Guanglei; Wang, Tao; Inorganica Chimica Acta; vol. 392; (2012); p. 374 - 379 View in Reaxys With aluminum (III) chloride, Friedel-Crafts Acylation Khalaf, Abedawn I.; Huggan, Judith K.; Suckling, Colin J.; Gibson, Colin L.; Stewart, Kirsten; Giordani, Federica; Barrett, Michael P.; Wong, Pui Ee; Barrack, Keri L.; Hunter, William N.; Journal of Medicinal Chemistry; vol. 57; nb. 15; (2014); p. 6479 - 6494 View in Reaxys Stage 1: With aluminum (III) chloride in 1,2-dichloro-ethane, Time= 0.166667h, T= 0 °C Stage 2: in 1,2-dichloro-ethane, T= 0 - 50 °C Siddaraju, Yogesh; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 13; nb. 48; (2015); p. 11651 11656 View in Reaxys O

Rx-ID: 1548750 View in Reaxys 4/824 Yield 95 %

Conditions & References With Au nanoparticles covalently bonded to HS/SO3H functionalized periodic mesoporous organosilica (Et) in water, Time= 1.5h, T= 80 °C Zhu, Feng-Xia; Wang, Wei; Li, He-Xing; Journal of the American Chemical Society; vol. 133; nb. 30; (2011); p. 11632 11640 View in Reaxys

91 %

With methanesulfonic acid, iron(II) chloride tetrahydrate in 1,2-dichloro-ethane, Time= 18h, T= 60 °C , Inert atmosphere Park, Jungmin; Yeon, Jihee; Lee, Phil Ho; Lee, Kooyeon; Tetrahedron Letters; vol. 54; nb. 33; (2013); p. 4414 - 4417 View in Reaxys

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90 %

General procedure for hydration of alkynes General procedure: Reactions were performed in a magnetically stirred round bot-tomed flask fitted with a condenser and placed in a temperature controlled oil bath. Zeolite (H) (100 mg) was added to the well stirred solution of alkyne (2 mmol) and H2O (8 mmol) and the reac-tion mixture was allowed to stir at 100 °C. After disappearance of the alkyne (monitored by TLC) or after an appropriate time, the reaction mixture was cooled to room temperature, diluted with ethyl acetate. The catalyst was separated by filtration and the removal of solvent in vacuo yielded residue. and it was further puri-fied by column chromatography using silica gel (100–200 mesh) to afford pure products. All the products were identified on the basisof H1 and C13NMR spectral data. With water in neat (no solvent), Time= 20h, T= 100 °C , Green chemistry, regioselective reaction Mameda, Naresh; Peraka, Swamy; Marri, Mahender Reddy; Kodumuri, Srujana; Chevella, Durgaiah; Gutta, Naresh; Nama, Narender; Applied Catalysis A: General; vol. 505; (2015); p. 213 - 216; Art.No: 15488 View in Reaxys

85 %

With water in Cyclooctan, Time= 2h, T= 100 °C Jin, Xiongjie; Oishi, Takamichi; Yamaguchi, Kazuya; Mizuno, Noritaka; Chemistry - A European Journal; vol. 17; nb. 4; (2011); p. 1261 - 1267 View in Reaxys

84 %

19 : 4.2. General procedure for the synthesis of methyl ketones (2a-x). 4.2.19. Propiophenone (2s) General procedure: To the mixture of terminal alkyne (1mmol), water (2.0 equiv), and acetic acid (2 mL), silver tetrafluoroborate (5 molpercent) was added. The mixture was stirred at 110°C for 10 h. Water (10 mL) was added and the solution was extracted with ethyl acetate (3×8 mL), the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography to give the pure sample. 4.2.19. Propiophenone (2s). 1H NMR (400 MHz, CDCl3): η=7.93 (d, J=7.6 Hz, 2H), 7.49-7.52 (m, 1H), 7.41 (t, J=7.6 Hz, 2H), 2.13-2.98 (m, 2H), 1.19 (t, J=7.6 Hz, 3H). 13C NMR (100 MHz, CDCl3): η=200.7, 136.9, 132.8, 128.5, 127.9, 31.7, 8.2. MS (EI) m/z: 134, 105, 77, 51. With silver tetrafluoroborate, water in acetic acid, Time= 10h, T= 110 °C , regioselective reaction Chen, Zheng-Wang; Ye, Dong-Nai; Qian, Yi-Ping; Ye, Min; Liu, Liang-Xian; Tetrahedron; vol. 69; nb. 30; (2013); p. 6116 6120 View in Reaxys

84 %

Solvent-free and water-medium alkyne hydration reactions General procedure: The solvent-free and water-medium alkyne hydrations were carried out in a 10 mL reaction vial for a specified temperature and time. For solvent-free alkyne hydration, alkyne (0.3 mmol), was added to 50 mg Fe3O4(at)SiO2(at)SiO2SH-Au (containing 0.004 mmol Au); it was then stirred at 70 °C for 2 h. For water-medium alkyne hydration, alkyne (0.3 mmol) and 50 mg Fe3O4(at)SiO2(at)SiO2-SH-Au (containing 0.004 mmol Au) were taken in water (4 ml) and the mixture was stirred at 80°C for 2 h for the synthesis of different ketones. After completion of the reaction, the reaction mixture was filtered and purified by passing through a column of silica gel, eluting with 10 percent EtOAc in hexane to afford the pure products. With water, Time= 2h, T= 80 °C , Green chemistry, Temperature Rostamizadeh, Shahnaz; Estiri, Hamid; Azad, Mohammad; Journal of the Iranian Chemical Society; vol. 13; nb. 7; (2016); p. 1367 - 1374 View in Reaxys

83 %

6.19 : 4.2 General procedure for the hydration of alkynes 1a–1n and 1p–1t General procedure: The reaction mixture of In(OTf)3 (11.2 mg, 2 mol percent), PTSA (57.1 mg, 30 mol percent), DCE (2.0 mL), alkynes 1a–1n or 1p–1t (1.0 mmol) and water (0.2 mL) in a 10 mL flask or in a 10 mL sealed tube was stirred at reflux and monitored periodically by TLC. Upon completion, DCE was removed under reduced pressure using an aspirator, and then the residue was purified by flash chromatography (PE/EA) on silica gel to afford corresponding carbonyl compounds 2a–2n or 2p– 2t. With indium(III) triflate, water, toluene-4-sulfonic acid in 1,2-dichloro-ethane, Time= 12h, Sealed tube, Reflux, regioselective reaction Gao, Qi; Li, Shenyan; Pan, Yingming; Xu, Yanli; Wang, Hengshan; Tetrahedron; vol. 69; nb. 19; (2013); p. 3775 - 3781 View in Reaxys

80 %

With sulfuric acid in water, Time= 1h, T= 280 °C

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An, Jingyi; Bagnell, Laurence; Cablewski, Teresa; Strauss, Christopher R.; Trainor, Robert W.; Journal of Organic Chemistry; vol. 62; nb. 8; (1997); p. 2505 - 2511 View in Reaxys 80 %

With iron(III) chloride, water, silver(I) triflimide in 1,4-dioxane, Time= 60h, T= 95 °C , regioselective reaction Cabrero-Antonino, Jose R.; Leyva-Perez, Antonio; Corma, Avelino; Chemistry - A European Journal; vol. 18; nb. 35; (2012); p. 11107 - 11114 View in Reaxys

74 %

3.3. Typical procedure for synthesis of ketones General procedure: To the mixture of phenylacetylene (1 mmol), water (3.0 mL),silver perfluorooctanesulfonate (5 molpercent) and perfluorooctane sulfonateacid (2 molpercent) was added. The mixture was stirred at 100 Cfor 8 h. The solution was extracted with n-hexane (diethyl ether)(3 5 mL), the combined extract was dried with anhydrous MgSO4. The rest of the solution was used for the next cycle of reaction. Theextraction solvent was removed and the crude product was separatedby column chromatography to give the pure sample. With Perfluorooctanesulfonic acid, C8AgF17O3S*H2O in water, Time= 8h, T= 100 °C , Darkness, regioselective reaction Dong, Qizhi; Li, Ningbo; Qiu, Renhua; Wang, Jinying; Guo, Cancheng; Xu, Xinhua; Journal of Organometallic Chemistry; vol. 799-800; (2015); p. 122 - 127 View in Reaxys

73 %

With phosphoric acid, boron trifluoride in acetonitrile, benzene, Time= 1h, T= 60 - 70 °C Pourzal, Ali-A.; Bonnet, Peter-H.; Monatshefte fuer Chemie; vol. 114; (1983); p. 809 - 812 View in Reaxys

57 %

With ethanol, antimony pentafluoride in 1,2-dichloro-ethane, Time= 2h, T= 90 °C Saito, Akio; Umakoshi, Masaharu; Yagyu, Naomi; Hanzawa, Yuji; Organic Letters; vol. 10; nb. 9; (2008); p. 1783 - 1785 View in Reaxys

56 %

General procedure: To a tube equipped with a condenser was added aniline (1, 0.2 mmol), diphenylacetylene (2, 0.4 mmol), PdCl2 (3.5 mg,0.02 mmol), CuCl2·2H2O (6.8 mg, 0.04 mmol), DPPE (7.9 mg,0.02 mmol), 1,10-phenanthroline monohydrate (15.9 mg, 0.08 mmol), AgOTf (10.3mg, 0.04 mmol), H2O (18 mg, 18 μL, 1 mmol), dioxane (0.25 mL). Themixture was stirred and heated at 100 °C for 24 h until the substratedisappeared as monitored by TLC. The reaction mixture was cooled down to room temperature,dried under vacuum and purified by column chromatography on silica gel toobtain the desired products 3 (petroleumether:ethyl acetate = 20:1). With 1,10-Phenanthroline, copper(II) choride dihydrate, silver trifluoromethanesulfonate, aniline, 1,2-bis-(diphenylphosphino)ethane, palladium dichloride in 1,4-dioxane, water, Time= 24h, T= 100 °C Wang, Zhiwei; Fan, Wenyou; Deng, Guo-Jun; Zhou, Wang; Tetrahedron Letters; vol. 56; nb. 40; (2015); p. 5449 - 5452 View in Reaxys

50 %

With tetrafluoroboric acid in chloroform-d1, water, Time= 1h, T= 60 °C , Reagent/catalyst, Time La Sorella, Giorgio; Sperni, Laura; Ballester, Pablo; Strukul, Giorgio; Scarso, Alessandro; Catalysis Science and Technology; vol. 6; nb. 15; (2016); p. 6031 - 6036 View in Reaxys

35 %

General procedure for the hydration of alkyne 3 catalyzed by S-COPNA (NP) resin General procedure: The mixture of 3 (232 mg, 2.0 mmol) and S-COPNA (NP) resin (59 mg, 0.2 mmol) in H2O (4 mL) was stirred (600 rpm) for 8 h under reflux conditions (bath temp. 120 °C). The catalyst was filtered and washed with H2O and heptane. One drop of saturated NaHCO3 was added and the organic layer was evaporated under reduced pressure. The residue was purified by column chromatography with heptane–acetone (20:1) as eluent to afford 23 (225 mg, 84percent). With water, Time= 8h, Reflux Tanemura, Kiyoshi; Suzuki, Tsuneo; Tetrahedron Letters; vol. 58; nb. 10; (2017); p. 955 - 958 View in Reaxys

80 % Chromat.

With water, bis(trifluoromethanesulfonyl)amide in 1,4-dioxane, Time= 40h, T= 100 °C

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Tsuchimoto; Joya; Shirakawa; Kawakami; Synlett; nb. 12; (2000); p. 1777 - 1778 View in Reaxys 50 % Chromat.

With silver hexafluoroantimonate, copper(I) trifluoromethanesulfonate benzene in dichloromethane, Time= 14h, T= 95 °C Deng, Chen-Liang; Song, Ren-Jie; Guo, Sheng-Mei; Wang, Zhi-Qiang; Li, Jin-Heng; Organic Letters; vol. 9; nb. 24; (2007); p. 5111 - 5114 View in Reaxys

98 %Chromat.

With water, bis(trifluoromethanesulfonyl)amide in 1,4-dioxane, Time= 20h, T= 80 °C , Reagent/catalyst, regioselective reaction Cabrero-Antonino, Jose R.; Leyva-Perez, Antonio; Corma, Avelino; Chemistry - A European Journal; vol. 19; nb. 26; (2013); p. 8627 - 8633 View in Reaxys

85 %Spectr. With gallium(III) triflate, water, acetic acid, Time= 12h, T= 100 °C Liang, Shengzong; Hammond, Gerald B.; Xu, Bo; Chemical Communications; vol. 51; nb. 5; (2015); p. 903 - 906 View in Reaxys 94 %Chromat.

With sulfuric acid, water in 1,4-dioxane, Time= 2h, T= 120 °C , Microwave irradiation Cheng, Yunfeng; Zhao, Qingshan; Li, Yang; Peng, Wenchao; Zhang, Guoliang; Zhang, Fengbao; Fan, Xiaobin; RSC Advances; vol. 6; nb. 80; (2016); p. 76151 - 76157 View in Reaxys With trifluorormethanesulfonic acid, water in 2,2,2-trifluoroethanol, Time= 48h, T= 40 °C , Inert atmosphere Liu, Sensheng; Liu, Huan; Zhou, Haifeng; Liu, Qixing; Lv, Jinliang; Organic Letters; vol. 20; nb. 4; (2018); p. 1110 - 1113 View in Reaxys With trifluorormethanesulfonic acid, water in 2,2,2-trifluoroethanol, Time= 48h, T= 40 °C Liu, Huan; Liu, Sensheng; Zhou, Haifeng; Liu, Qixing; Wang, Chunqin; RSC Advances; vol. 8; nb. 27; (2018); p. 14829 14832 View in Reaxys O O

Rx-ID: 1548754 View in Reaxys 5/824 Yield 97 %

Conditions & References With carbon monoxide, water, platinum(II) chloride in 1,4-dioxane Chang, Hsu-Kai; Datta, Swarup; Das, Arindam; Odedra, Arjan; Liu, Rai-Shung; Angewandte Chemie - International Edition; vol. 46; nb. 25; (2007); p. 4744 - 4747 View in Reaxys

68 %, 22 %

With water, Aliquat 336, PtCl4-CO in various solvent(s), Time= 4.5h, T= 110 °C , p= 1034.3Torr Baidossi, Wael; Lahav, Michal; Blum, Jochanan; Journal of Organic Chemistry; vol. 62; nb. 3; (1997); p. 669 - 672 View in Reaxys

52 %, 43 %

With water, PtCl4-CO in tetrahydrofuran, Time= 3h, T= 80 °C , p= 1034.3Torr Baidossi, Wael; Lahav, Michal; Blum, Jochanan; Journal of Organic Chemistry; vol. 62; nb. 3; (1997); p. 669 - 672 View in Reaxys

28 - 45 %, 18 - 30 %

39; 40 :Example 39 To a solution in which 0.005 g of methyl(triphenylphosphine)gold (0.01 mmol) was dissolved in 3 ml of methanol, 0.12 g of 1phenyl-1-propyne (1 mmol) and an aqueous solution in which 0.05 g of concentrated sulfuric acid (0.5 mmol) was dissolved in 0.5 ml of water were added.

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After stirring at 70° C. for 5 hours, propiophenone was obtained in 45percent yield, and benzyl methyl ketone was obtained in 30percent yield (catalyst turnover number: 75). ; Example 40 A reaction was carried out in the same manner as in Example 39, except for using 0.001 g of methyl(triphenylphosphine)gold (0.002 mmol). As a result, propiophenone was obtained in 28percent yield, and benzyl methyl ketone was obtained in 18percent yield (catalyst turnover number: 230) With water, methyl(triphenylphosphine)gold(I), sulfuric acid in methanol, Time= 5h, T= 70 °C , Product distribution / selectivity Patent; Mizushima, Eiichiro; Hayashi, Teruyuki; Sato, Kazuhiko; Tanaka, Masato; US2005/143597; (2005); (A1) English View in Reaxys 94 % Chromat.

With dimesitylboron hydride, dihydrogen peroxide, 1) THF, 60 min, 25 deg C, 2) THF - NaH2PO4 buffer, Yields of byproduct given. Title compound not separated from byproducts Pelter, Andrew; Singaram, Saraswathi; Brown, Herbert; Tetrahedron Letters; vol. 24; nb. 13; (1983); p. 1433 - 1436 View in Reaxys With {HB(2,4,6-Me3C6H2)2}2, 1) THF, 20 deg C, 5 min, 2) oxidation, Yield given. Multistep reaction. Yields of byproduct given Pelter, Andrew; Smith, Keith; Buss, Dieter; Norbury, Andrew; Tetrahedron Letters; vol. 32; nb. 43; (1991); p. 6239 - 6242 View in Reaxys With dimesitylboron hydride, dihydrogen peroxide, 1) THF, 60 min, 25 deg C, 2) THF - NaH2PO4 buffer; comparison with other hydroboration agents, Product distribution Pelter, Andrew; Singaram, Saraswathi; Brown, Herbert; Tetrahedron Letters; vol. 24; nb. 13; (1983); p. 1433 - 1436 View in Reaxys

76 % Chromat., 24 % Chromat.

With sodium hydroxide, lithium borohydride, dihydrogen peroxide, ethyl acetate, different ratios, Product distribution Brown, Herbert C.; Somayaji, Vishwanatha; Narasimhan, S.; Journal of Organic Chemistry; vol. 49; nb. 25; (1984); p. 4822 - 4827 View in Reaxys With sodium hydroxide, ThxBHI*SMe2, dihydrogen peroxide, directive effect of thexylhaloborane-methyl sulfide in the hydroboration of alkynes; further reagents; multistep reaction, Product distribution Cha, Jin Soon; Min, Soo Jin; Kim, Jong Mi; Kwon, Oh Own; Tetrahedron Letters; vol. 34; nb. 32; (1993); p. 5113 - 5116 View in Reaxys With palladium (II) nitrate, 2-amino-phenol in 1,4-dioxane, Time= 5h, T= 120 °C Shimada, Tomohiro; Yamamoto, Yoshinori; Journal of the American Chemical Society; vol. 124; nb. 43; (2002); p. 12670 12671 View in Reaxys Stage 1: With Me2S-BH2I, iodine in dichloromethane, Time= 24h, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in methanol, dichloromethane, T= 0 - 20 °C , Title compound not separated from byproducts Clay, Julia M.; Vedejs, Edwin; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5766 - 5767 View in Reaxys Stage 1: With Lut*BH2I, iodine in dichloromethane, Time= 24h, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in methanol, dichloromethane, T= 0 - 20 °C , Title compound not separated from byproducts Clay, Julia M.; Vedejs, Edwin; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5766 - 5767 View in Reaxys With silica-supported HgSO4/H2SO4/H2O in dichloromethane, Time= 16h, T= 40 °C Mello, Rossella; Alcalde-Aragones, Ana; Gonzalez-Nunez, Maria Elena; Tetrahedron Letters; vol. 51; nb. 32; (2010); p. 4281 - 4283

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View in Reaxys With methanol, bis(triphenylphosphine)gold(I) hexafluorophosphate, sulfuric acid in water, Inert atmosphere, Sealed tube, Heating Carriedo, Gabino A.; Lopez, Salome; Suarez-Suarez, Silvia; Presa-Soto, David; Presa-Soto, Alejandro; European Journal of Inorganic Chemistry; nb. 9; (2011); p. 1442 - 1447 View in Reaxys With 2CHF3O3S*C29H35NO6P2Pt, water, sodium dodecyl-sulfate, T= 80 °C , Micellar solution Trentin, Francesco; Chapman, Andrew M.; Scarso, Alessandro; Sgarbossa, Paolo; Michelin, Rino A.; Strukul, Giorgio; Wass, Duncan F.; Advanced Synthesis and Catalysis; vol. 354; nb. 6; (2012); p. 1095 - 1104 View in Reaxys 33 %Chromat., 66 %Chromat.

With water, bis(trifluoromethanesulfonyl)amide in 1,4-dioxane, Time= 20h, T= 80 °C , Concentration, regioselective reaction Cabrero-Antonino, Jose R.; Leyva-Perez, Antonio; Corma, Avelino; Chemistry - A European Journal; vol. 19; nb. 26; (2013); p. 8627 - 8633 View in Reaxys With triflato[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I), water, 5-methyl-dihydro-furan-2-one, Time= 2.5h, T= 120 °C , Green chemistry, Time Gatto, Mattia; Baratta, Walter; Belanzoni, Paola; Belpassi, Leonardo; Del Zotto, Alessandro; Tarantelli, Francesco; Zuccaccia, Daniele; Green Chemistry; vol. 20; nb. 9; (2018); p. 2125 - 2134 View in Reaxys O

Rx-ID: 2007966 View in Reaxys 6/824 Yield 93 %

Conditions & References With potassium permanganate, Rexyn 101 H ion exchange resin in dichloromethane, Time= 5.45h, Heating Shaabani, Ahmad; Teimouri, Fatemeh; Lee, Donald G.; Synthetic Communications; vol. 33; nb. 6; (2003); p. 1057 - 1065 View in Reaxys

92 %

With potassium permanganate on Zeolite beta in 1,2-dichloro-ethane, Time= 96h, Ambient temperature Sreekumar; Padmakumar, Raghavakaimal; Tetrahedron Letters; vol. 38; nb. 29; (1997); p. 5143 - 5146 View in Reaxys

92 %

With sodium bromate, sulfuric acid, silica gel, Time= 3h, T= 20 °C Shaabani, Ahmad; Soleimani, Kamal; Bazgir, Ayoob; Synthetic Communications; vol. 34; nb. 18; (2004); p. 3303 - 3315 View in Reaxys

92 %

6.1 :Example 6 Extension of Benzylic OxidationThe mild conditions of the optimized aqueous Rh2(cap)4/tert-Butyl hydroperoxide allylic oxidation reaction of the present invention provides an improved means for conducting benzylic oxidation and dione formation. Anhydrous benzylic reactions are discussed in Catino, A. J. et al. (2005) Org. Lett., 7(23):5167-5170), and involve Rh2(cap)4 (1.0 mol percent); NaHCO3 (50 mol percent), t-BuOOH (5.0 equiv.), DCE, room temperature, 16 hour incubation) (Table 9). A survey of suitable substrates for benzylic oxidation reactions includes the following compounds (see, Catino, A. J. et al. (2005) Org. Lett., 7(23):5167-5170). Reactions were conducted using Rh2(cap)4 (1.0 mol percent); NaHCO3 (50 mol percent), t-BuOOH (5.0 equiv.), DCE, room temperature, 16 hour incubation) (Table 10).General Procedure for Benzylic Oxidations Catalyzed by Dirhodium(II) Caprolactamate in Water. 1-Phenylbutane was stirred vigorously in water at room temperature in a screwcap vial. Rh2(cap)4 (1.0 mol percent) was added to the vial followed by dropwise (2 drops/sec) addition of 5.0 equiv. of T-HYDRO.(R).. The reaction was slightly exothermic, bubbled, and the mixture became dark purple-red in color. The vial was loosely capped and stirred at room temperature or heated to 40° C. while monitored by TLC and gas chromatography. Upon consumption of the starting arylhydrocarbon, the reaction was extracted twice into diethyl ether. The organic extracts were combined, dried over anhydrous MgSO4, filtered, then concentrated on a under reduced pressure to a crude oil which was purified

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via silica gel chromatography (hexanes/ethyl acetate) to afford the desired product. Benzylic oxidations run under aqueous conditions are reported in McLaughlin, E. C.; Doyle, M. P. J. Org. Chem. 2008, 73, 4317 With tert.-butylhydroperoxide, sodium hydrogencarbonate, Rh2(cap)4 in 1,2-dichloro-ethane, T= 20 - 40 °C , Benzylic oxidation Patent; UNIVERSITY OF MARYLAND, COLLEGE PARK; US2009/93638; (2009); (A1) English View in Reaxys 90 %

With potassium permanganate, copper(II) sulfate, Time= 70h, Ambient temperature, other reagent, reaction time, Product distribution Noureldin, Nazih A.; Zhao, Dongyuan; Lee, Donald G.; Journal of Organic Chemistry; vol. 62; nb. 25; (1997); p. 8767 - 8772 View in Reaxys

88 %

With oxygen in water, Time= 6.5h, Reflux Albadi, Jalal; Alihosseinzadeh, Amir; Jalali, Mehdi; Mansournezhad, Azam; Applied Organometallic Chemistry; vol. 32; nb. 3; (2018); Art.No: E4193 View in Reaxys

86 %

With tert.-butylhydroperoxide, dirhodium(II) tetra-2-(methanesulfonylimino)pyrrolidine in water, Time= 20h, T= 20 °C Wusiman, Abudureheman; Tusun, Xiarepati; Lu, Chong-Dao; European Journal of Organic Chemistry; nb. 16; (2012); p. 3088 - 3092 View in Reaxys

86 %

9 : Example 9: Propylbenzene0.2 mmol,Copper powder 0.05mmolAnd Selectfluor 0.06 mmol are added in turn into a 10 mL pressure-resistant sealed container.Add 2 mL of a mixture of acetonitrile and water (CH3CN/H2O = 100:1).The mixture was stirred at room temperature and the reaction was monitored by TLC.After 4 hours, the reaction solution was diluted with 10 mL of dichloromethane.Filter to obtain clear solutionEvaporate the solvent and use column chromatography (eluent ratio: petroleum ether to ethyl acetate volume ratio 20:1)After separation, the eluent was collected and the solvent was distilled off to obtain phenyl acetone in a yield of 86percent. With copper, Selectfluor in water, acetonitrile, Time= 4h, T= 20 °C , Reagent/catalyst, Temperature Patent; Zhejiang University of Technology; Liu Yunkui; Zhang Wei; Zhang Wenxia; (9 pag.); CN105085205; (2018); (B) Chinese View in Reaxys

85 %

With manganese(IV) oxide, potassium permanganate in dichloromethane, Time= 24h, T= 20 °C Shaabani, Ahmad; Mirzaei, Peiman; Naderi, Soheila; Lee, Donald G.; Tetrahedron; vol. 60; nb. 50; (2004); p. 11415 - 11420 View in Reaxys

85 %

With sodium azide, [bis(acetoxy)iodo]benzene, water in acetonitrile, Time= 0.5h, T= 20 °C Telvekar, Vikas N.; Sasane, Kulbhushan A.; Synthetic Communications; vol. 42; nb. 9; (2012); p. 1325 - 1329 View in Reaxys

84 %

With dihydrogen peroxide in water, Time= 9h, T= 80 °C , p= 760.051Torr , Green chemistry Hosseini-Sarvari, Mona; Ataee-Kachouei, Tahereh; Moeini, Fatemeh; RSC Advances; vol. 5; nb. 12; (2015); p. 9050 - 9056 View in Reaxys

83 %

7 : synthesis of propiophenone To the 25 mL Schlenk reaction tube was added 0.5 equivalents of NHPI and dried in vacuo for 15 minutes. The oxygen balloon was added and the acetonitrile lmL, 1.0 part by weight of t-butyl nitrite and 0.5 mmol of propylbenzene were added in an oxygen atmosphere. On the poly tetrafluoro plug after the oil into the pot, 80 ° C reaction 24h After completion of the reaction, the solvent acetonitrile was removed by concentration under reduced pressure, and the column eluting with petroleum ether / ethyl acetate (η: 50: 1) was used to obtain propiophenone Yield 83percent, light yellow solid; With tert.-butylnitrite, N-hydroxyphthalimide in acetonitrile, Time= 24h, T= 80 °C , Schlenk technique

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Patent; University of Science and Technology of China; Kang Yanbiao; Liu Jie; (15 pag.); CN107011133; (2017); (A) Chinese View in Reaxys 82 %

With potassium permanganate, iron(III) chloride in acetone, Time= 16h, T= -78 - 20 °C Lai, Sheng; Lee, Donald G.; Tetrahedron; vol. 58; nb. 49; (2002); p. 9879 - 9887 View in Reaxys

80 %

With Marshall's acid, copper(II) sulfate in water, acetonitrile, Time= 1h, T= 75 - 80 °C Perumal, P. Thirumalai; Bhatt, M. Vivekananda; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 20; nb. 2; (1981); p. 153 - 155 View in Reaxys

80 %

With sodium bromate, tetra(n-butyl)ammonium hydrogensulfate in water, acetonitrile, Time= 24h, T= 80 °C , Product distribution, Further Variations: Reagents Shaabani, Ahmad; Bazgir, Ayoob; Abdoli, Masoomeh; Synthetic Communications; vol. 32; nb. 5; (2002); p. 675 - 678 View in Reaxys

80 %

With ruthenium trichloride, iodobenzene, potassium peroxymonosulfate in water, acetonitrile, Time= 26h, T= 20 °C , Inert atmosphere Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor V.; Tetrahedron; vol. 66; nb. 31; (2010); p. 5745 - 5752 View in Reaxys

80 %

With ruthenium trichloride, Oxone, iodobenzene in water, acetonitrile, Time= 26h, T= 20 °C Yusubov, Mekhman S.; Zhdankin, Viktor V.; Mendeleev Communications; vol. 20; nb. 4; (2010); p. 185 - 191 View in Reaxys

79 %

With sodium bromate, 1-n-butyl-3-methylimidazolim bromide, Time= 11h, T= 70 °C Shaabani, Ahmad; Farhangi, Elham; Rahmati, Abbas; Monatshefte fur Chemie; vol. 139; nb. 8; (2008); p. 905 - 908 View in Reaxys

75 %

With potassium permanganate, manganese(II) sulfate, Time= 5.3h, T= 20 °C Shaabani, Ahmad; Rahmati, Abbas; Sharifi, Masoumeh; Rad, Jafar Mogimi; Aghaaliakbari, Behnaz; Farhangi, Elham; Lee, Donald G.; Monatshefte fur Chemie; vol. 138; nb. 7; (2007); p. 649 - 651 View in Reaxys

72 %

With tert.-butylhydroperoxide, [(pymox-Me2)2RuCl2]+BF4- in water, Time= 16h, T= 20 °C Yi, Chae S.; Kwon, Ki-Hyeok; Lee, Do W.; Organic Letters; vol. 11; nb. 7; (2009); p. 1567 - 1569 View in Reaxys

72.4 %

Experimental Section General procedure: In a general procedure, into a three-neck flask, 3 mmol of aromatics, 5 mL of acetic acid, 5 mol percent of NHPI, and 0.83 mol percent of CoSPc were added. Thereafter, 02 was bubbled at 2.5 mL/s into the flask. The oxidation was carried out at 90°C under stirring. Oxidation process was monitored by TLC. After the original substrate was exhausted, the reaction solution was concentrated under reduced pressure and the reside was separated on silica gel. The products were confirmed by 'H NMR, and the assignments and yields determination of the volatile products, such as benzyl aldehyde, were estimated according to the retention times and peak areas by GC. With N-hydroxyphthalimide, oxygen in acetic acid, Time= 4h, T= 90 °C Zhou, Yulu; Lin, Shasha; Bian, Yinghui; Xia, Daohong; Xiang, Yuzhi; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 55B; nb. 5; (2016); p. 624 - 628 View in Reaxys

70 %

With Montmorillonite-K10, water, potassium bromide, Time= 24h, T= 80 °C Dohi, Toshifumi; Takenaga, Naoko; Goto, Akihiro; Fujioka, Hiromichi; Kita, Yasuyuki; Journal of Organic Chemistry; vol. 73; nb. 18; (2008); p. 7365 - 7368

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View in Reaxys 70 %

2. Experimental details and characterization datafor products 2 General procedure: A mixture of 1 (0.2 mmol), Co(ClO4)2 (0.02 mmol), Oxone (1.2 mmol), CH3CN (2 mL) and H2O (2 mL) was stirred in a sealed tube at 25 °C for 3 h. After the reaction was completed (as monitored by TLC), the mixture was placed and allowed to separate into layers. Then the upper organic layer was separated, dried with anhydrous Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by preparative TLC (petroleum ether/ethyl acetate = 10:1, v/v) to yield 2. With oxone, cobalt(II) perchlorate in water, acetonitrile, Time= 3h, T= 25 °C , Sealed tube Yang, Yiwen; Ma, Hongxia; Tetrahedron Letters; vol. 57; nb. 47; (2016); p. 5278 - 5280 View in Reaxys

69 %

With aluminum oxide, potassium permanganate, water in 1,2-dichloro-ethane, Time= 167h, Ambient temperature Zhao; Lee; Synthesis; nb. 9; (1994); p. 915 - 916 View in Reaxys

64 %

With N-hydroxyphthalimide in pyridine, anodic oxidation Masui, Masaichiro; Hara, Seijiro; Ueshima, Takahiro; Kawaguchi, Tetsuo; Ozaki, Shigeko; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 11; (1983); p. 4209 - 4212 View in Reaxys

62 %

With oxygen, chloroamine-T, meso-tetrakis(tetraphenyl)porphyrin iron(III) chloride in acetonitrile, Time= 24h, T= 20 °C , p= 760Torr Li, Shi-Jun; Wang, Yan-Guang; Tetrahedron Letters; vol. 46; nb. 46; (2005); p. 8013 - 8015 View in Reaxys

62 %

With [bis(acetoxy)iodo]benzene, tert-butyl hydroxyperoxide, 3-chloro-benzenecarboperoxoic acid in 2,2,2-trifluoroethanol, Time= 12h, T= 20 °C Xu, Yuan; Yang, Zhenping; Hu, Jiantao; Yan, Jie; Synthesis (Germany); vol. 45; nb. 3; (2013); p. 370 - 374; Art.No: SS-2012-F0873-OP View in Reaxys

59 %

58 %

With potassium permanganate in acetonitrile, Time= 30h, T= 20 °C Shaabani, Ahmad; Tavasoli-Rad, Farahnaz; Lee, Donald G.; Synthetic Communications; vol. 35; nb. 4; (2005); p. 571 - 580 View in Reaxys

57 %

With potassium permanganate, Montmorillonite K10, Time= 20h, T= 23 °C

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Shaabani, Ahmad; Bazgir, Ayoob; Teimouri, Fatemeh; Lee, Donald G; Tetrahedron Letters; vol. 43; nb. 29; (2002); p. 5165 5167 View in Reaxys 55 %

With iodobenzene, 3-chloro-benzenecarboperoxoic acid, potassium bromide in water, Time= 18h, T= 60 °C Xu, Yuan; Hu, Jian Tao; Yan, Jie; Chinese Chemical Letters; vol. 23; nb. 8; (2012); p. 891 - 894 View in Reaxys

52 %

With tert.-butylhydroperoxide, [C6H5CH2N(CH3)2H]2[Ru(2,6-pyridinedicarboxylate)Cl3] in water, Time= 32h, T= 40 °C , Catalytic behavior Zhang, Yuecheng; Zhao, Liyuan; Zhang, Hongyu; Huang, Rong; Zhao, Jiquan; Applied Organometallic Chemistry; vol. 31; nb. 9; (2017); Art.No: E3709 View in Reaxys

47.3 %

With tert.-butylhydroperoxide, 5Cu(2+)*10C2H8N2*2BH3O3*14H2O*(VO)12O6(B18O36(OH)6)(10-), acetic acid in water, acetonitrile, Time= 24h, T= 65 °C Feng, Yuquan; Zhong, Zhiguo; Wang, Hongwei; Fan, Huitao; Bi, Dongqin; Wang, Lu; Xing, Zhengzheng; Qiu, Dongfang; Chemistry - A European Journal; vol. 23; nb. 41; (2017); p. 9962 - 9967 View in Reaxys

46.8 %

With CuCr2O4, dihydrogen peroxide in acetonitrile, Time= 12h, T= 75 °C Acharyya, Shankha S.; Ghosh, Shilpi; Siddiqui, Nazia; Konathala, L. N. Sivakumar; Bal, Rajaram; RSC Advances; vol. 5; nb. 7; (2015); p. 4838 - 4843 View in Reaxys

44.3 %

With tert.-butylhydroperoxide in acetonitrile, Time= 5h, T= 69.84 °C Zhu, Mingxia; Wei, Xin; Li, Bodong; Yuan, Youzhu; Tetrahedron Letters; vol. 48; nb. 52; (2007); p. 9108 - 9111 View in Reaxys

42 %

With iodosylbenzene, racemic (salen)Mn(III) in acetonitrile, Time= 3h, T= 0 °C Lee, Nam Ho; Lee, Chang-Seob; Jung, Duk-Sang; Tetrahedron Letters; vol. 39; nb. 11; (1998); p. 1385 - 1388 View in Reaxys

38 %

With tert.-butylhydroperoxide, [V12B18Zn3O63H12]*5H2O*10H3N*10H(1+)*3C4H13N3, acetic acid in water, acetonitrile, Time= 24h, T= 65 °C Chen, Hong; Deng, Youqian; Yu, Zhengbao; Zhao, Huishuang; Yao, Qingxia; Zou, Xiaodong; Baeckvall, Jan-E.; Sun, Junliang; Chemistry of Materials; vol. 25; nb. 24; (2013); p. 5031 - 5036 View in Reaxys

37 %

With C26H28F6MnN6O7S2, dihydrogen peroxide, acetic acid in water, acetonitrile, Time= 0.5h, T= 20 °C , Inert atmosphere Shen, Duyi; Miao, Chengxia; Wang, Shoufeng; Xia, Chungu; Sun, Wei; Organic Letters; vol. 16; nb. 4; (2014); p. 1108 1111 View in Reaxys

34 %

30 %

With [MnIV 2 (μ-O)3(1,4,7-trimethyl-1,4,7-triazacyclononane)2](PF6)2, dihydrogen peroxide, trichloroacetic acid in water, acetonitrile, Time= 16h, T= 0 - 20 °C Saisaha, Pattama; Buettner, Lea; Van Der Meer, Margarethe; Hage, Ronald; Feringa, Ben L.; Browne, Wesley R.; De Boer, Johannes W.; Advanced Synthesis and Catalysis; vol. 355; nb. 13; (2013); p. 2591 - 2603 View in Reaxys

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22 % Chromat.

With 3,3-dimethyldioxirane in acetone, Time= 72h, Ambient temperature Kuck, Dietmar; Schuster, Andreas; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 46; nb. 9; (1991); p. 1223 1226 View in Reaxys

75 % Chromat.

With <bis(salicylidene-N-methyl 3-(4'-hydroxy phenyl)propionate)>cobalt, oxygen, isobutyraldehyde in acetonitrile Punniyamurthy; Bhatia, Beena; Reddy, M. Madhava; Maikap, Golak C.; Iqbal, Javed; Tetrahedron; vol. 53; nb. 22; (1997); p. 7649 - 7670 View in Reaxys With cerium(IV) oxide, sodium bromate in 1,4-dioxane, water, acetic acid, Time= 24h, T= 95 °C Shi, Qi-Zeng; Wang, Jian-Ge; Cai, Kun; Synthetic Communications; vol. 29; nb. 7; (1999); p. 1177 - 1181 View in Reaxys

27 % Chromat.

With 1H-imidazole, sodium periodate, Mn(III)meso-(p-sulfonato-Ph)4-η-Br8-porphyrin*Amberl.IRA400 in water, acetonitrile, Time= 10h, T= 20 °C Tangestaninejad; Habibi; Mirkhani; Moghadam; Molecules; vol. 7; nb. 2; (2002); p. 264 - 270 View in Reaxys

55 % Chromat.

With ethoxylated η-cyclodextrin, dihydrogen peroxide, ferric nitrate, Time= 1h, T= 65 °C Maksimov; Ivanova; Karakhanov; Petroleum Chemistry; vol. 44; nb. 6; (2004); p. 432 - 437 View in Reaxys

87 % Chromat.

With dihydrogen peroxide, dinuclear cobalt(III)-copper(II) macrocyclic in water, acetonitrile, Time= 5h, T= 80 °C Golchoubian; Ghaziani, A. Nemati Kharat; Polish Journal of Chemistry; vol. 79; nb. 5; (2005); p. 825 - 830 View in Reaxys

41 % Chromat.

With 1H-imidazole, sodium periodate, Mn(III)-salen supported on Amberlite IRA-200 in water, acetonitrile, Time= 1h, T= 20 °C Mirkhani, Valiollah; Moghadam, Majid; Tangestaninejad, Shahram; Bahramian, Bahram; Monatshefte fur Chemie; vol. 138; nb. 12; (2007); p. 1303 - 1308 View in Reaxys With oxygen in water, acetonitrile, T= 5 - 10 °C , p= 759.826Torr , Irradiation, chemoselective reaction Ni, Lingli; Ni, Ji; Lv, Yuan; Yang, Ping; Cao, Yong; Chemical Communications; nb. 16; (2009); p. 2171 - 2173 View in Reaxys 18 : Examples 11-18 These examples further illustrate the process of this invention for the oxidation of diphenyl methane to benzophenone, n-propyl benzene to propiophenone, n-butyl benzene to n-butyrophenone 4-ethyl toluene to 4-methyl acetophenone and benzhydrol to benzophenone at different reaction conditions. [0122] The oxidation reactions were carried out using the catalyst prepared in Example-10 and by the method similar to that described in Example-1 except that the reaction conditions are different. The results obtained at different reaction conditions are given in Tables 3 and 4. With oxygen, hydrotalcite like catalyst in Nil, Time= 5h, T= 150 °C , p= 1368.09Torr , Conversion of starting material Patent; Council of Scientific and Industrial Research; US2004/192972; (2004); (A1) English View in Reaxys 20 : Examples 19-22 These examples further illustrate the process of this invention for the oxidation of ethyl benzene to acetophenone, n-propyl benzene to propiophenone, n-butyl benzene to n-butyrophenone and diphenyl methane to benzophenone with continuous removal of the reaction water during the oxidation reaction, using the catalyst prepared in Example-1. [0125] The catalytic oxidation reactions were carried out, by the method similar to that described in Example-1 except that a Dean-Stark trap was used between the reactor and the reflux condenser, each of the reactions is carried out with or without using a non-aqueous solvent, each of the reactions was carried out under reflux and the water formed in each of the reactions was removed continuously during the reaction. The results obtained are given in Table 5.

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With oxygen, hydrotalcite like catalyst in Nil, Time= 20h, p= 1140.08Torr , Heating / reflux, Conversion of starting material Patent; Council of Scientific and Industrial Research; US2004/192972; (2004); (A1) English View in Reaxys 107 mg

With ruthenium trichloride, iodobenzene, potassium hydrogen persulfate in water, acetonitrile, Time= 26h, T= 20 °C Yusubov, Mekhman S.; Zagulyaeva, Aleksandra A.; Zhdankin, Viktor V.; Chemistry - A European Journal; vol. 15; nb. 42; (2009); p. 11091 - 11094 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 8h, T= 20 °C , chemoselective reaction Islam; Roy, Anupam Singha; Mondal, Paramita; Mubarak, Manir; Mondal, Sanchita; Hossain, Dildar; Banerjee, Satabdi; Santra; Journal of Molecular Catalysis A: Chemical; vol. 336; nb. 1-2; (2011); p. 106 - 114 View in Reaxys With ruthenium trichloride, Oxone in water, acetonitrile, Time= 24h, T= 20 °C Chen, Jiang-Min; Zeng, Xiao-Mei; Middleton, Kyle; Yusubov, Mekhman S.; Zhdankin, Viktor V.; Synlett; nb. 11; (2011); p. 1613 - 1617 View in Reaxys

92 %Chromat.

With tert.-butylhydroperoxide in water, Time= 12h, T= 80 °C Zou, Chao; Zhang, Zhijuan; Xu, Xuan; Gong, Qihan; Li, Jing; Wu, Chuan-De; Journal of the American Chemical Society; vol. 134; nb. 1; (2012); p. 87 - 90 View in Reaxys With tert.-butylhydroperoxide, Time= 5h, T= 90 °C , Neat (no solvent) Anand, Narani; Reddy, Kannapu Hari Prasad; Prasad, Ganjala Venkata Siva; Rama Rao, Kamaraju Seetha; Burri, David Raju; Catalysis Communications; vol. 23; (2012); p. 5 - 9 View in Reaxys With tert.-butylhydroperoxide, acetic acid in water, acetonitrile, Time= 18h, T= 65 °C Yang, Xiu-Li; Xie, Ming-Hua; Zou, Chao; He, Yabing; Chen, Banglin; O'Keeffe, Michael; Wu, Chuan-De; Journal of the American Chemical Society; vol. 134; nb. 25; (2012); p. 10638 - 10645 View in Reaxys

90 %Chromat.

General procedure General procedure: To a solution of aromatic compound 1a-q (1 mmol) in CH3CN (6 mL) and H2O (0.5 mL) were added KBr (0.5 mmol) and Oxone (2.2 mmol), and the mixture was stirred at 45°C. After completion (monitored by TLC), the reaction mixture was filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous Na2S2O3 and brine, dried over anhydrous Na2SO4. Removal of the solvent under vacuum afforded the crude product, which was purified by column chromatography using hexane/ethyl acetate as eluent (20 - 80 : 1). With Oxone, water, potassium bromide in acetonitrile, T= 45 °C Yin, Lixia; Wu, Jingjing; Xiao, Juan; Cao, Song; Tetrahedron Letters; vol. 53; nb. 33; (2012); p. 4418 - 4421 View in Reaxys General procedure for the oxidation of diphenylmethane to benzophenone General procedure: In a 25 mL pressure tube, ZnBr2 (10 mol percent) and a stirring bar were added. After the addition of diphenylmethane (1 mmol), trifluoroacetic acid (0.2 mL) and 1,4-dioxane (2 mL) by syringe, H2O2 (4 mmol; 30percent aqueous) was added in one pot to the solution and the final solution was kept at 100 °C for 16 h. Then hexadecane (100 mg) and ethyl acetate (3 mL) were injected, a part of solution was taken for GC and GC–MS analysis after properly mixed. All the products are commercially available. #10; With dihydrogen peroxide, trifluoroacetic acid, zinc dibromide in 1,4-dioxane, water, Time= 16h, T= 100 °C Wu, Xiao-Feng; Tetrahedron Letters; vol. 53; nb. 45; (2012); p. 6123 - 6126 View in Reaxys

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54 %Chromat.

With sodium periodate, water in acetonitrile, Time= 6h Saeedi, Mohammad Saleh; Tangestaninejad, Shahram; Moghadam, Majid; Mirkhani, Valiollah; Mohammadpoor-Baltork, Iraj; Khosropour, Ahmad Reza; Polyhedron; vol. 49; nb. 1; (2013); p. 158 - 166 View in Reaxys

75 %Chromat.

General procedure for oxidation of alkanes with NaIO4 catalyzed by [Mn(TNH2PP)Cl(at)MWCNT] General procedure: To a mixture of alkane (1 mmol), [Mn(TNH2PP)Cl(at)MWCNT] (350 mg, 0.05 mmol) and imidazole (0.2 mmol) in CH3CN (10 mL) was added a solution of NaIO4 (2 mmol) in H2O (10 mL). The reaction mixture was stirred magnetically at room temperature. The progress of the reaction was monitored by GC. At the end of the reaction, the reaction mixture was diluted with Et2O (20 mL) and filtered. The catalyst was thoroughly washed with Et2O and combined washings and filtrates were purified on silica-gel plates or with a silica-gel column. IR and 1H NMR spectral data confirmed the identities of the products. With 1H-imidazole, sodium periodate, 5,10,15,20-tetrakis-(4-aminophenyl) manganese(III) porphyrin chloride in water, acetonitrile, Time= 2h, T= 25 °C Araghi, Mehdi; Bokaei, Forough; Polyhedron; vol. 53; (2013); p. 15 - 19 View in Reaxys 2.3 Catalytic activity tests#10; General procedure: Typically, 50 mg of catalyst, 1 mmol of substrate, and 3 mmol of 70percent t-BuOOH (Sigma Aldrich) were taken in a RB flask and constantly stirred at 363 K for 5 h under solvent-free conditions. Unless otherwise specified the above reaction conditions are applicable. The catalyst was separated by filtration and analyzed by GC (GC-17A model, M/s. Shimadzu Instruments, Japan) consisting of FID and OV-1 capillary column (0.53 mm × 30 m) using toluene as external standard. The product identification was made by GC–MS (QP5050 model, M/s. Shimadzu Instruments, Japan) consisting of DB-5 column (0.32 mm dia. and 25 m long, M/s. J & W Scientific, USA). The separated catalyst was washed with methanol and dried under vacuum prior to reuse.#10; With tert.-butylhydroperoxide in neat (no solvent), Time= 5h, T= 89.84 °C Neeli, Chinna Krishna Prasad; Narani, Anand; Marella, Ravi Kumar; Rama Rao, Kamaraju Seetha; Burri, David Raju; Catalysis Communications; vol. 39; (2013); p. 5 - 9 View in Reaxys

75 %Chromat.

With dihydrogen peroxide in water, Time= 10h, T= 60 °C , Catalytic behavior, Reagent/catalyst Islam, Sk. Manirul; Paul, Sumantra; Roy, Anupam Singha; Banerjee, Satabdi; Ghosh, Kajari; Dey, Ram Chandra; Santra; Transition Metal Chemistry; vol. 38; nb. 6; (2013); p. 675 - 682 View in Reaxys

50 %Chromat.

2.3 Catalytic experiments General procedure: All of the reactions were carried out at room temperature with magnetic stirring. To a mixture of alkene or alkane (1 mmol), Mn(TPP)ClIm-MIL-101(100 mg) in CH3CN (10 ml), a solution of NaIO4 (2 mmol) in H2O (10 ml) was added. The reaction mixture was stirred at room temperature. The progress of the reaction was monitored by GC. At the end of the reaction, the mixture was diluted with Et2O (20 ml) and filtered. The catalyst was thoroughly washed with Et2O and the combined washings and filtrates were purified on a silica gel plates or a silica gel column to afford the product. With sodium periodate in water, acetonitrile, Time= 4h, T= 20 °C , Catalytic behavior Zadehahmadi, Farnaz; Tangestaninejad, Shahram; Moghadam, Majid; Mirkhani, Valiollah; Mohammadpoor-Baltork, Iraj; Khosropour, Ahmad R.; Kardanpour, Reihaneh; Journal of Solid State Chemistry; vol. 218; (2014); p. 56 - 63 View in Reaxys With tert.-butylhydroperoxide, acetic acid in water, acetonitrile, Time= 6h, T= 60 °C Song, Guo-Qiang; Lu, Ying-Xun; Zhang, Qi; Wang, Fan; Ma, Xiao-Kun; Huang, Xian-Feng; Zhang, Zhi-Hui; RSC Advances; vol. 4; nb. 57; (2014); p. 30221 - 30224 View in Reaxys With tert.-butylhydroperoxide, C6H2N6 (2-)*Mn(2+)*2Cl(1-)*HO(1-)*Mn(3+), acetic acid, m-dichlorobenzene in water, acetonitrile, Time= 10h, T= 80 °C

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Liao, Pei-Qin; Li, Xu-Yu; Bai, Jie; He, Chun-Ting; Zhou, Dong-Dong; Zhang, Wei-Xiong; Zhang, Jie-Peng; Chen, XiaoMing; Chemistry - A European Journal; vol. 20; nb. 36; (2014); p. 11303 - 11307 View in Reaxys General procedure for oxidation of alkyl aromatics General procedure: Alkyl aromatics (5 mmol) in 10 mL acetonitrile and the polymer supported cobalt catalyst (60 mg) were in turn introduced into a50 mL round bottomed flask equipped with a condenser and a thermometer in an oil bath. The reaction was carried under oxygen atmosphere (1 atm) with 1 mmol H2O2. Then, the catalyst wasremoved by filtration, and the solvent was evaporated in vacuum. The product was filtered, washed thoroughly with water and extracted with ether, then dried with anhydrous Na2SO4 and analyzed by GC and GC-MS. With dihydrogen peroxide, oxygen in water, acetonitrile, Time= 7h, T= 70 °C , p= 760.051Torr , Green chemistry, Catalytic behavior Islam, Sk Manirul; Ghosh, Kajari; Molla, Rostam Ali; Roy, Anupam Singha; Salam, Noor; Iqubal, Md Asif; Journal of Organometallic Chemistry; vol. 774; (2015); p. 61 - 69 View in Reaxys 91 %Chromat.

2.3 A typical procedure for the oxidation of ethylbenzene General procedure: A mixture of Mn-CPF-1 (0.01mmol based on Mn), ethylbenzene (0.1mmol) and TBHP (0.15mmol) in water (5mL) was stirred at room temperature for 12h. The mixture was centrifuged, and the solid was washed with CH3CN for several times. The recovered solid catalyst was used in the successive run. The supernatant was extracted with hexane (2mL). The identity of the product was determined by GC–MS, and compared with the authentic samples analyzed under the same conditions, while the yield was obtained by GC analysis in the presence of an internal standard of naphthalene. With tert.-butylhydroperoxide in water, Time= 12h, T= 20 °C Zou, Chao; Zhao, Min; Wu, Chuan-De; Catalysis Communications; vol. 66; (2015); p. 116 - 120 View in Reaxys

95 %Chromat.

2.3 General procedure for oxidation of alkyl arenes General procedure: Alkyl arenes (1 mmol) were added in a two round bottomed glass flask containing a mixture of cobalt-chitosan (5 mol percent, 0.023 g) and NHPI (1 mol percent, 0.016 g)in 10 mL 1,2-dichlorobenzene. The flask was fitted with a reflux condenser and mixture was heated at 80°C with continuous bubbling of air with flow rate of 15 mL min−1. After completion of the reaction (progress of the reaction followed by TLC), catalyst was separated by an external magnet and the reaction mixture was analyzed by gas chromatography. With N-hydroxyphthalimide in 1,2-dichloro-benzene, Time= 4h, T= 80 °C , Catalytic behavior Shaabani, Ahmad; Boroujeni, Mahmoud Borjian; Sangachin, Mona Hamidzad; Journal of Chemical Sciences; vol. 127; nb. 11; (2015); p. 1927 - 1935 View in Reaxys With tert.-butylhydroperoxide, C73H50CoN4O11*2C3H7NO in acetonitrile, Time= 20h, T= 80 °C Zhang, Zengqi; Li, Jun; Yao, Yahong; Sun, Shu; Crystal Growth and Design; vol. 15; nb. 10; (2015); p. 5028 - 5033 View in Reaxys Oxidation of alkyl aromatics General procedure: In a typical procedure, to a mixture of catalyst (0.5 mmol), acetonitrile (10 mL) and alkyl aromatics (5 mmol) were added tert-butyl hydroperoxide (15 mmol) in turn. Samples were withdrawn periodically. After required hours, the reaction mixture was cooled to room temperature. With tert.-butylhydroperoxide in acetonitrile, Time= 24h, T= 80 °C , Green chemistry Xu; Li; Chen; Asian Journal of Chemistry; vol. 27; nb. 10; (2015); p. 3555 - 3558 View in Reaxys With bismuth(III) tungsten(VI) oxide, oxygen, Time= 5h, Irradiation, Green chemistry Liu, Ying; Chen, Lang; Yuan, Qing; He, Jie; Au, Chak-Tong; Yin, Shuang-Feng; Chemical Communications; vol. 52; nb. 6; (2016); p. 1274 - 1277 View in Reaxys

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95 %Chromat.

With porous chitosan–manganese dioxide nanohybrid, air in para-xylene, Time= 7h, T= 100 °C , Green chemistry Shaabani, Ahmad; Borjian Boroujeni, Mahmoud; Laeini, Mohmmad Sadegh; Applied Organometallic Chemistry; vol. 30; nb. 3; (2016); p. 154 - 159 View in Reaxys

40.6 %Chromat.

2.4. Catalytic oxidation of alkylbenzene General procedure: A mixtureofalkylbenzene(0.4mmol),tert-butylhydroperoxide(TBHP,1.6mmol),catalyst(0.02mmol)andacetonitrile(2.5mL)wasstirredat80 °C for20h.Afterthereaction,theidentityoftheproductwasdeterminedbyusinggas-chromatography(GC),compared withtheauthenticsamplesanalyzedunderthesameconditions. TheyieldofproductwasalsoobtainedbyGCanalysiswith a flame-ionization detector(FID)usingacapillarySE-54column. With tert.-butylhydroperoxide, C52H34CuN4O12 (2-)*2C2H7N*Zn(2+) in acetonitrile, Time= 20h, T= 80 °C Zhang, Zengqi; Su, Xiaoqin; Yu, Fan; Li, Jun; Journal of Solid State Chemistry; vol. 238; (2016); p. 53 - 59 View in Reaxys

82.6 %Chromat.

With tert.-butylhydroperoxide in water, Time= 6h, T= 80 °C , Green chemistry Ma, Zhishuang; Zhang, Hongye; Yang, Zhenzhen; Ji, Guipeng; Yu, Bo; Liu, Xinwei; Liu, Zhimin; Green Chemistry; vol. 18; nb. 7; (2016); p. 1976 - 1982 View in Reaxys 2.4. Typical procedure for catalytic oxidation General procedure: Alkylbenzene (0.1 mmol), tert-butylhydroperoxide (TBHP, 0.5 mmol), catalyst (0.005 mmol)and H2O (2.0 mL) were added into a flask and stirred at 80 °C for 20 h. When the reactionfinished, the identity of the product was determined by using gas chromatography (GC),compared with authentic samples analyzed under the same conditions. The yield of productwas also obtained by GC analysis with a flame-ionization detector (FID) using a capillarySE-54 column. With tert.-butylhydroperoxide, C42H16F10N6 (2-)*Co(2+)*C2H7N in water, Time= 20h, T= 80 °C Xu, Weixia; Zhang, Zengqi; Zhao, Xin; Li, Jun; Journal of Coordination Chemistry; vol. 70; nb. 4; (2017); p. 746 - 755 View in Reaxys

89 %Chromat.

With tert.-butylhydroperoxide in hexane, T= 130 °C , Sealed tube Tan, Jiajing; Zheng, Tianyu; Yu, Yuqi; Xu, Kun; RSC Advances; vol. 7; nb. 25; (2017); p. 15176 - 15180 View in Reaxys

73 %Chromat.

With N-hydroxyphthalimide, Zn3Co2W19, 4Cu(2+)*C52H22N4O16 (10-)*Cu(2+)*30H2O*4C3H7NO*7C2H8N(1+)*7NO3 (1-), tetrabutylammomium bromide, oxygen in acetonitrile, Time= 24h, T= 50 °C , p= 760.051Torr Zhao, Min; Wu, Chuan-De; ChemCatChem; vol. 9; nb. 7; (2017); p. 1192 - 1196 View in Reaxys With oxygen in neat (no solvent), Time= 5h, T= 120 °C , p= 6000.6Torr , Autoclave, Green chemistry Lin, Xiu; Nie, Zhenzhen; Zhang, Liyun; Mei, Shuchuan; Chen, Yuan; Zhang, Bingsen; Zhu, Runliang; Liu, Zhigang; Green Chemistry; vol. 19; nb. 9; (2017); p. 2164 - 2173 View in Reaxys With tert.-butylhydroperoxide in water, Time= 7h, T= 20 °C Liu, Wengang; Zhang, Leilei; Liu, Xin; Liu, Xiaoyan; Yang, Xiaofeng; Miao, Shu; Wang, Wentao; Wang, Aiqin; Zhang, Tao; Journal of the American Chemical Society; vol. 139; nb. 31; (2017); p. 10790 - 10798 View in Reaxys

94 %Chromat.

With tert.-butylhydroperoxide in water, Time= 12h, T= 20 °C Ding, Zheng-Dong; Zhu, Wei; Li, Tao; Shen, Rui; Li, Yunxing; Li, Zaijun; Ren, Xuehong; Gu, Zhi-Guo; Dalton Transactions; vol. 46; nb. 34; (2017); p. 11372 - 11379 View in Reaxys

54 %Chromat.

IV. Synthesis of products 4 General procedure: A mixture of hydrocarbons (0.2 mmol), complex 3b (0.02 mmol), Oxone (1.2 mmol), CH3CN (2 mL) and H2O (2 mL) was stirred in a sealed tube at 25 °C for 16 h. After the reaction was completed (as monitored by TLC or GC), the

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solution was layered. Then the upper solvent was separated and evaporated in vacuo. The resulting residue was purified by preparative TLC (petroleum ether/ethyl acetate = 10:1, v/v) to yield 4. With Oxone, C30H32Cl2I2MnN4O2 in water, acetonitrile, Time= 16h, T= 25 °C , Sealed tube Yang, Yiwen; Zhong, Wei; Nie, Binmei; Chen, Jiangmin; Wei, Zhenhong; Liu, Xiaoming; Journal of Organometallic Chemistry; vol. 853; (2017); p. 136 - 142 View in Reaxys With tert.-butylhydroperoxide in water, Time= 7h, T= 20 °C Li, Xingwei; Chinese Journal of Catalysis; vol. 39; nb. 1; (2018); p. 1 - 3 View in Reaxys 91 %Chromat.

With tert.-butylhydroperoxide, C56H36ClMnN12*2C3H7NO in water, Time= 20h, T= 80 °C , Sealed tube, Catalytic behavior, Reagent/catalyst Yao, Yahong; Du, Yanxia; Li, Jun; Wang, Chen; Zhang, Zengqi; Zhao, Xin; Applied Organometallic Chemistry; vol. 32; nb. 3; (2018); Art.No: E4184 View in Reaxys O

Rx-ID: 3543576 View in Reaxys 7/824 Yield 93 %

Conditions & References With In(OAc)3, phenylsilane in ethanol, Time= 1.5h, T= 20 °C Miura, Katsukiyo; Yamada, Yusuke; Tomita, Mitsuru; Hosomi, Akira; Synlett; nb. 11; (2004); p. 1985 - 1989 View in Reaxys

89 %

With methanol, bis(cyclopentadienyl)titanium (III) chloride in tetrahydrofuran, Time= 2h, T= -25 - 20 °C , Product distribution, Further Variations: Reaction partners Moisan, Lionel; Hardouin, Christophe; Rousseau, Bernard; Doris, Eric; Tetrahedron Letters; vol. 43; nb. 11; (2002); p. 2013 - 2015 View in Reaxys

87 %

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], potassium carbonate, isopropyl alcohol, Time= 5h, T= 85 °C , Inert atmosphere, Schlenk technique, chemoselective reaction Chen, Shu-Jie; Lu, Guo-Ping; Cai, Chun; RSC Advances; vol. 5; nb. 17; (2015); p. 13208 - 13211 View in Reaxys

70 %

With dibutyltin, Dibutyldifluorotin, lithium iodide in tetrahydrofuran, T= 20 °C , Reduction Moriuchi-Kawakami, Takayo; Matsuda, Haruo; Shibata, Ikuya; Miyatake, Masato; Suwa, Toshihiro; Baba, Akio; Bulletin of the Chemical Society of Japan; vol. 72; nb. 3; (1999); p. 465 - 470 View in Reaxys

63 %

With tri-n-butyl-tin hydride, dibutyl tin diiodide in tetrahydrofuran, Time= 1h, Ambient temperature Kawakami, Takayo; Miyatake, Masato; Shibata, Ikuya; Baba, Akio; Journal of Organic Chemistry; vol. 61; nb. 1; (1996); p. 376 - 379 View in Reaxys

60 %

With methyl-cyclopentane, HUSY-zeolite, Time= 15h, T= 130 °C , sealed tube Sani Souna Sido, Abdelkarim; Chassaing, Stefan; Kumarraja, Mayilvasagam; Pale, Patrick; Sommer, Jean; Tetrahedron Letters; vol. 48; nb. 33; (2007); p. 5911 - 5914 View in Reaxys

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With carbon monoxide, cobalt tetracarbonyl hydride in dichloromethane, T= 22 °C , various amount of catalyst, reagent, Rate constant Roth, Jerome A.; Grega, Kevin; Orchin, Milton; Journal of Organometallic Chemistry; vol. 342; (1988); p. 129 - 136 View in Reaxys Reaction Steps: 2 1: neat (no solvent) in neat (no solvent) vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.2, page 97 - 113 View in Reaxys Reaction Steps: 2 1: neat (no solvent) in neat (no solvent) vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.2, page 97 - 113 View in Reaxys Reaction Steps: 2 1: neat (no solvent) in neat (no solvent) vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.2, page 97 - 113 View in Reaxys With D-glucose, ene-reductase P1-E01, glucose dehydrogenase-105, NADPH - oxidized form in aq. buffer, Time= 6h, T= 30 °C , Enzymatic reaction, stereoselective reaction Martínez-Montero, Lía; Gotor, Vicente; Gotor-Fernández, Vicente; Lavandera, Iván; ACS Catalysis; vol. 8; nb. 3; (2018); p. 2413 - 2419 View in Reaxys O

Rx-ID: 5931083 View in Reaxys 8/824 Yield 90 %

Conditions & References 4 :General procedure: 1- (4-bromophenyl) ethanol (201 mg, 1.0 mmol)Was dissolved in 2.0 mL of DMF solvent,To this was added iodic acid (194 mg, 1.1 mmol)And TEMPO (7.8 mg, 0.05 mmol) were mixed.The mixture was stirred in an Ar atmosphere at room temperature for 2 hours.To the reaction mixture was added aqueous sodium thiosulfate solution and extracted with diethyl ether: hexane = 1: 1 (3 × 10 mL).After washing the extract with saturated brine, the aqueous layer was extracted with ether (10 ml), and the organic layers were combined and dried with anhydrous sodium sulfate.The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (ethyl acetate: hexane = 1: 4) to obtain 4'-bromoacetophenone as a final product (yield 99percent). Treatment was carried out in the same manner except that a primary alcohol or a secondary alcohol was used instead of 1- (4-bromophenyl) ethanol used in Example 4 based on the following general formula (3) Were obtained in yields shown in Table 2, respectively. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, iodic acid in N,N-dimethyl-formamide, Time= 2h, T= 20 °C , Inert atmosphere, Reagent/catalyst, Temperature Patent; CHIBA UNIVERSITY; GODO SHIGEN COMPANY LIMITED; TOGO, HIDEO; IMAI, SHO; MIYAMOTO, MICHIHIKO; (10 pag.); JP2018/2680; (2018); (A) Japanese View in Reaxys Herstellung von 1-Phenyl-<1-14 C>propan-1-on Speer; Jeanes; ; (1958); p. 662 View in Reaxys Billek; Herrmann; Monatshefte fuer Chemie; vol. 88; (1957); p. 735,737

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View in Reaxys Herstellung von 1-Phenyl-<2-14 C>propan-1-on Roberts; Brandenberger; Journal of the American Chemical Society; vol. 79; (1957); p. 5484,5485 View in Reaxys Klages,F. et al.; Chemische Berichte; vol. 94; (1961); p. 1464 - 1469 View in Reaxys Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606 View in Reaxys Deuchert,K. et al.; Chemische Berichte; vol. 112; (1979); p. 2045 - 2061 View in Reaxys Olah,G.A. et al.; Journal of the American Chemical Society; vol. 84; (1962); p. 2733 - 2740 View in Reaxys Bloch,R. et al.; Tetrahedron; vol. 24; (1968); p. 5971 - 5989 View in Reaxys Lamm,B.; Samuelsson,B.; Acta Chemica Scandinavica (1947-1973); vol. 24; (1970); p. 561 - 568 View in Reaxys Graf; Graser; Sitzius; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 302; nb. 8; (1969); p. 561 - 571 View in Reaxys Kossanyi,J.; Bulletin de la Societe Chimique de France; (1965); p. 714 - 722 View in Reaxys Fauvarque,J.; Fauvarque,J.-F.; Bulletin de la Societe Chimique de France; (1969); p. 160 - 171 View in Reaxys Rabesiaka,J.; Bulletin de la Societe Chimique de France; (1970); p. 1440 - 1445 View in Reaxys Castelli,F.; Cannone,P.; Bulletin de la Societe Chimique de France; (1974); p. 317 - 330 View in Reaxys Guyon,R.; Villa,P.; Bulletin de la Societe Chimique de France; (1975); p. 2593 - 2598 View in Reaxys Ishido,Y. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1977); p. 521 - 530 View in Reaxys Traynelis,V.J. et al.; Journal of Organic Chemistry; vol. 29; (1964); p. 123 - 129 View in Reaxys Gassman,P.G.; Richmond,G.D.; Journal of Organic Chemistry; vol. 31; (1966); p. 2355 - 2357 View in Reaxys Padwa,A. et al.; Journal of Organic Chemistry; vol. 33; nb. 4; (1968); p. 1317 - 1322 View in Reaxys McKinney,M.A.; So,E.C.; Journal of Organic Chemistry; vol. 37; nb. 18; (1972); p. 2818 - 2822 View in Reaxys Huenig,S.; Wehner,G.; Synthesis; (1975); p. 180 - 182 View in Reaxys Blomberg,C.; Hartog,F.A.; Synthesis; (1977); p. 18 - 30 View in Reaxys Ohno,A. et al.; Tetrahedron Letters; (1972); p. 4993 - 4996 View in Reaxys Rasmussen,J.K.; Hassner,A.; Tetrahedron Letters; (1973); p. 2783 - 2786 View in Reaxys Cuvigny; Normant; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 265; (1967); p. 245 View in Reaxys Henrick et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 2467,2475 View in Reaxys Meyers; Comins; Tetrahedron Letters; (1978); p. 5179 View in Reaxys Suggs; Journal of the American Chemical Society; vol. 101; (1979); p. 489 View in Reaxys Sheehan; Umezawa; Journal of Organic Chemistry; vol. 38; (1973); p. 3771,3773 View in Reaxys

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Balachandran; George; Tetrahedron; vol. 29; (1973); p. 2119,2124, 2127 View in Reaxys Moriconi; Shimakawa; Journal of Organic Chemistry; vol. 37; (1972); p. 196,207 View in Reaxys Warner et al.; Journal of the Chemical Society; (1962); p. 1232 View in Reaxys Schaumann et al.; Chemische Berichte; vol. 112; (1979); p. 1769,1775 View in Reaxys Alper et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 4330,4331 View in Reaxys Watt; Journal of Organic Chemistry; vol. 39; (1974); p. 2799 View in Reaxys Shalaby et al.; Croatica Chemica Acta; vol. 52; (1979); p. 353,359 View in Reaxys Moussa; Abdalla; Journal of Applied Chemistry; vol. 20; (1970); p. 256 View in Reaxys Wasserman; Lipshutz; Tetrahedron Letters; (1975); p. 4611 View in Reaxys Glatz; Razus; Revue Roumaine de Chimie; vol. 11; (1966); p. 551,554 View in Reaxys Olah et al.; Synthesis; (1977); p. 677 View in Reaxys Abe et al.; Chemistry Letters; (1977); p. 645 View in Reaxys Deuchert et al.; Synthesis; (1973); p. 777 View in Reaxys Dahlig et al.; Roczniki Chemii; vol. 34; (1960); p. 401,409; ; nb. 361a; (1961) View in Reaxys Reinheckel; Jahnke; Chemische Berichte; vol. 97; (1964); p. 2661 View in Reaxys Pasynkiewicz et al.; Roczniki Chemii; vol. 38; (1964); p. 67,77 View in Reaxys Maruyama; Bulletin of the Chemical Society of Japan; vol. 34; (1961); p. 105 View in Reaxys Sisti et al.; Journal of Chemical and Engineering Data; vol. 9; (1964); p. 108 View in Reaxys Buttero et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1974); p. 1411 View in Reaxys Meyers; Smith; Journal of the American Chemical Society; vol. 92; (1970); p. 1084 View in Reaxys Alper; Prickett; Inorganic Chemistry; vol. 16; (1977); p. 67,71 View in Reaxys Kende et al.; Synthetic Communications; vol. 8; (1978); p. 59 View in Reaxys Jurjew et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 415,439; ; nb. 24638; (1960) View in Reaxys Dorofeenko et al.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 2424,2476,2478 View in Reaxys Narasaka et al.; Bulletin of the Chemical Society of Japan; vol. 45; (1972); p. 3724 View in Reaxys Olah; Welch; Journal of the American Chemical Society; vol. 100; (1978); p. 5396,5397 View in Reaxys Sahan; Mori; Chemistry Letters; (1972); p. 793,794,795 View in Reaxys Bavin; Journal of Medicinal Chemistry; vol. 9; (1966); p. 52 View in Reaxys Gassman et al.; Journal of the American Chemical Society; vol. 97; (1975); p. 1600 View in Reaxys Bertsch; Reinheckl; Fette, Seifen, Anstrichmittel; vol. 64; (1962); p. 881; ; vol. 58; nb. 6686f; (1963) View in Reaxys

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Kazi; Merchant; Current Science; vol. 35; (1966); p. 255 View in Reaxys Kossanyi; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 250; (1960); p. 3487 View in Reaxys Bestmann; Tetrahedron Letters; nb. 4; (1960); p. 7,9 View in Reaxys Frainnet et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 261; (1965); p. 1329 View in Reaxys House et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 4099,4104 View in Reaxys Sharetkin; Boghosian; Analytical Chemistry; vol. 33; (1961); p. 640,641-644 View in Reaxys Turowa-Poljak et al.; Neftekhimiya; vol. 4; (1964); p. 603; ; p. 240 View in Reaxys Granito; Schultz; Journal of Organic Chemistry; vol. 28; (1963); p. 879 View in Reaxys Fel'dman et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 35; (1962); p. 1364,1309; ; vol. 57; nb. 11064; (1962) View in Reaxys Negeshi; Idacavage; Tetrahedron Letters; (1979); p. 845,847 View in Reaxys Belinka; Hassner; Journal of Organic Chemistry; vol. 44; (1979); p. 4712 View in Reaxys Mukaiyama; Echigo; Chemistry Letters; (1978); p. 49 View in Reaxys Julliard; Guillemonat; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 266; (1968); p. 817; ; vol. 69; nb. 51484t; (1968) View in Reaxys Elkik et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 270; (1970); p. 246 View in Reaxys Heiszwolf; Kloosterziel; Recueil des Travaux Chimiques des Pays-Bas; vol. 89; (1970); p. 1153,1158 View in Reaxys Takeda; Mukaiyama; Chemistry Letters; (1976); p. 477 View in Reaxys Jones et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 3369 View in Reaxys Quellette; Levin; Journal of the American Chemical Society; vol. 93; (1971); p. 471,472-476 View in Reaxys Bratchanskii; Komissarova; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 1661,1650 View in Reaxys Hashimoto; Tetrahedron; vol. 28; (1972); p. 217,218, 221, 225 View in Reaxys Selikson; Watt; Tetrahedron Letters; (1974); p. 3029 View in Reaxys Tufariello; Kissel; Tetrahedron Letters; (1966); p. 6145,6147 View in Reaxys Ito et al.; Bulletin of the Chemical Society of Japan; vol. 48; (1975); p. 2091 View in Reaxys Kakis et al.; Journal of Organic Chemistry; vol. 36; (1971); p. 4117,4122 View in Reaxys Patent; Bombrini-Parodi-Delfino Soc. p. Azioni; IT660910; (1961); ; vol. 62; nb. 7693; (1965) View in Reaxys Patent; Dow Chem.; US3280147; (1966); ; vol. 66; nb. 2372r; (1967) View in Reaxys Mukaiyama et al.; Chemistry Letters; (1972); p. 237 View in Reaxys Mayeda; Journal of the American Chemical Society; vol. 97; (1975); p. 4012,4013 View in Reaxys Barnhardt; McEwen; Journal of the American Chemical Society; vol. 89; (1967); p. 7009,7012 View in Reaxys Habeeb; Tuch; Journal of the Chemical Society, Chemical Communications; (1976); p. 696 View in Reaxys

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Makosza; Goetzen; Roczniki Chemii; vol. 46; (1972); p. 1239 View in Reaxys Turova-Polyak et al.; Moscow University Chemistry Bulletin (English Translation); vol. 22; nb. 3; (1967); p. 49; ; p. 68 View in Reaxys Pines; Goetschel; Journal of Catalysis; vol. 6; (1966); p. 380,383 View in Reaxys Shono et al.; Tetrahedron Letters; (1979); p. 165 View in Reaxys Kimura et al.; Chemistry Letters; (1979); p. 321 View in Reaxys Mukaiyama et al.; Chemistry Letters; (1973); p. 261 View in Reaxys Angelo; Normant; Izvestiya na Otdelenieto za Khimicheski Nauki (Bulgarska Akademiya na Naukite); vol. 8; (1975); p. 5,18,19 View in Reaxys Inoue et al.; Chemistry Letters; (1975); p. 1241 View in Reaxys Schwartz; Cannon; Journal of the American Chemical Society; vol. 96; (1974); p. 4721 View in Reaxys Alvernhe; Laurent; Tetrahedron Letters; (1973); p. 1057,1058 View in Reaxys Uemura; Nippon Kagaku Zasshi; vol. 89; (1968); p. 692,694; ; vol. 70; nb. 19678u View in Reaxys Ohki et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 766,767 View in Reaxys Mikolajczyk et al.; Tetrahedron Letters; (1975); p. 3757,3759 View in Reaxys Masuyama et al.; Chemistry Letters; (1977); p. 1439 View in Reaxys Mukaiyama et al.; Chemistry Letters; (1973); p. 715 View in Reaxys Fauvarque et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 275; (1972); p. 511,513 View in Reaxys Bratchanskii; Komissarova; Sov. Prog. Chem. (Engl. Transl.); vol. 41; nb. 4; (1975); p. 409,72,73 View in Reaxys Pasynkiewicz; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 21; (1964); p. 1,66 View in Reaxys Dimmel et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 3092 View in Reaxys De Puy; Accounts of Chemical Research; vol. 1; (1968); p. 33,41 View in Reaxys Brady; Ting; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1975); p. 456 View in Reaxys Olah et al.; Synthesis; (1979); p. 113 View in Reaxys Mukaiyama et al.; Bulletin of the Chemical Society of Japan; vol. 45; (1972); p. 3723 View in Reaxys Dimmel; Gharpure; Journal of the American Chemical Society; vol. 93; (1971); p. 3991,3994 View in Reaxys Inoue et al.; Bulletin of the Chemical Society of Japan; vol. 52; (1979); p. 469,470 View in Reaxys Alper; Keung; Journal of Organic Chemistry; vol. 37; (1972); p. 2566,2568,2571 View in Reaxys Georgiou et al.; Industrial and Engineering Chemistry Process Design and Development; vol. 13; (1974); p. 253 View in Reaxys Tomson; Eesti NSV Teaduste Akadeemia Toimetised, Keemia, Geoloogia; (1966); p. 447,448-453; ; vol. 66; nb. 94734 View in Reaxys Selikson; Watt; Journal of Organic Chemistry; vol. 40; (1975); p. 267 View in Reaxys

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Corey; Richman; Journal of the American Chemical Society; vol. 92; (1970); p. 5276 View in Reaxys Cainelli et al.; Tetrahedron Letters; (1973); p. 2491 View in Reaxys Jaeckel; Hanack; Chemische Berichte; vol. 110; (1977); p. 199,207 View in Reaxys Kupin; Petrow; J. Gen. Chem. USSR (Engl. Transl.); vol. 31; (1961); p. 2958,2758; ; vol. 57; nb. 2125; (1962) View in Reaxys Tscherkasowa; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 2846,2826 View in Reaxys Borowitz et al.; Journal of Organic Chemistry; vol. 31; (1966); p. 4031,4035 View in Reaxys McFarland; Harris; Journal of Organic Chemistry; vol. 32; (1967); p. 1273 View in Reaxys Wada et al.; Chemistry Letters; (1976); p. 381,383 View in Reaxys Dhami; Stothers; Canadian Journal of Chemistry; vol. 43; (1965); p. 498,499 View in Reaxys Lemetre; Pauri; Chimica e l'Industria (Milan, Italy); vol. 43; (1961); p. 1019 View in Reaxys Brown; Rogic; Journal of the American Chemical Society; vol. 91; (1969); p. 4304 View in Reaxys Henry-Basch et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 262; (1966); p. 598 View in Reaxys Blum et al.; Tetrahedron Letters; (1967); p. 3665 View in Reaxys Lee; Spitzer; Journal of Organic Chemistry; vol. 34; (1969); p. 1493 View in Reaxys Depuy et al.; Journal of Organic Chemistry; vol. 33; (1968); p. 2198 View in Reaxys Piekarski et al.; Bulletin de la Societe Chimique de France; (1968); p. 4063 View in Reaxys House; Larson; Journal of Organic Chemistry; vol. 33; (1968); p. 61,64 View in Reaxys Clesse et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 266; (1968); p. 1799 View in Reaxys Jullien; Thoi-Lai; Bulletin de la Societe Chimique de France; (1968); p. 4669 View in Reaxys Asinger et al.; Tetrahedron Letters; (1967); p. 631 View in Reaxys Pasynkiewicz; Maciaszek; Journal of Organometallic Chemistry; vol. 15; (1968); p. 301 View in Reaxys Freeman et al.; Tetrahedron; vol. 25; (1969); p. 3441 View in Reaxys Adam; Cheng; Journal of the American Chemical Society; vol. 91; (1969); p. 2109 View in Reaxys Noyce; Schiavelli; Journal of Organic Chemistry; vol. 33; (1968); p. 845 View in Reaxys Quellette; Levin; Journal of the American Chemical Society; vol. 90; (1968); p. 6889 View in Reaxys Tada et al.; Journal of Organometallic Chemistry; vol. 16; (1969); p. 215,216 View in Reaxys 5 : Preparation of propiophenone EXAMPLE 5 Preparation of propiophenone A mixture of 16 g/h of benzoic acid, 57 g/h of propionic acid and 14.5 g/h of water was evaporated in an evaporator and passed, together with 10 l/h of nitrogen, at 400° C., over 100 ml of a catalyst which contained 2.5percent by weight of sodium oxide, the remainder being anatase. The reaction gases were then cooled and were collected in a receiver.

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From the discharged two-phase mixture, the organic phase was analyzed by gas chromatography. The conversion of both carboxylic acids was 100percent. The selectivity with respect to propiophenone was 99percent. Patent; BASF Aktiengesellschaft; US4950763; (1990); (A) English View in Reaxys 46.2 : 2. 2. 2-(4-Benzyloxy-3-methoxycarbonylphenyl)-2-ethyl-1,3-dioxolane A mixture of 15 g of the propiophenone prepared above, 6.4 ml of ethylene glycol and 1 g of p-toluenesulphonic acid in 200 ml of toluene is heated under reflux for 10 hours. The toluene phase is then washed with 500 ml of a 5percent solution of sodium carbonate and then with water, dried over sodium sulphate and evaporated to dryness. The residual oil is chromatographed on alumina using toluene as the eluant. 11 g of purified oil are isolated. Patent; Synthelabo; US4690931; (1987); (A) English View in Reaxys 3 :3. Catalytic Hydroacylation of Ethylene Using 3-methyl-2-aminopyridyl Aldimines and Tristriphenylphosphinorhodium (1) Chloride. Into a stainless steel autoclave with a glass liner was placed 1.5 g. of the 3-methyl-2-aminopyridyl aldimine of benzaldehyde, 75 ml of tetrahydrofuran and 0.2 g. of RhCl(PPh3)3. The autoclave was flushed with ethylene, to remove any air, then pressurized with ethylene to 150 psi, followed by heating to 180 degrees C. for 14 hours. Upon cooling the resulting dark red liquid was concentrated to one-fourth its original volume and stirred with moist silica gel in 20 ml of CH2 Cl2 for 1 hour. Solvent was removed on the rotary evaporator and the product propiophenone was obtained by heating the silica gel at 130 degrees and 50 mm and collecting the distillate. Patent; Bell Telephone Laboratories, Incorporated; US4241206; (1980); (A) English View in Reaxys 1800%

3 :The yield of propiophenone, as a clear oil, was 0.45 g., 45percent yield based on starting aldimine and 1800percent yield based on the rhodium catalyst. Patent; Bell Telephone Laboratories, Incorporated; US4241206; (1980); (A) English View in Reaxys Hereinafter there are listed examples of ketones obtainalbe or obtained by the process of the invention: hexanone-3 decanone-4 nonadecan-2-one mesityl oxide propiophenone 3-methoxyacetophenone 3-phenoxyacetophenone o-chloroacetophenone o-chloropropiophenone m-chloroacetophenone ... Patent; Hoechst Aktiengesellschaft; US4266066; (1981); (A) English View in Reaxys 3 :General procedure: Instead of ABBX (4) 770 mg (2mmol) AFBX (2) and the reference example 1-1 similar reaction operation is performed, the organic layer by condensing a 4-methylbenzaldehyde 108 mg (yield 90percent, purity of 90percent)is obtained. The pH of the water layer, using a 1M hydrochloric acid 15 ml to about 2. Filtered precipitates are deposited, by vacuum drying methyltrifluoromethylbenzoic acid 2-iodo-5-bromoethylbenzene 593 mg (yield 91percent)is recovered. This 2-iodo-5-tribromoacetic benzoic acid and using a similar reaction operation embodiment 1-3, filtered precipitates are deposited, by vacuum drying 1-acetoxyethanephosphonate-5-bromo -1, 2- [...] -3-(1H)-one (ABBX (4)) 649 mg (yield 93percent)is obtained. With 1-acetoxy-5-bromo-1,2-benziodoxol-3(1H)-one in chloroform, Time= 24h, T= 60 Â°C , Reagent/catalyst

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Patent; Tokyo Chemical Industry Co., Ltd.; Togo, Hideo; Inuma, Masataka; Moriyama, Katsuhiko; Takatsuki, Kenichi; (9 pag.); JP2015/63501; (2015); (A) Japanese View in Reaxys

O OH

H HO

Rx-ID: 8811903 View in Reaxys 9/824 Yield 59 %

Conditions & References With Arthrobacter atrocyaneus in N,N-dimethyl-formamide, Time= 48h, T= 32 °C , Microbiological reaction, enantioselective reaction Silva, Camila R.; Souza, Juliana C.; Araujo, Lidiane S.; Kagohara, Edna; Garcia, Thais P.; Pelizzari, Vivian H.; Andrade, Leandro H.; Journal of Molecular Catalysis B: Enzymatic; vol. 83; (2012); p. 23 - 28 View in Reaxys

58 %

With palladium dichloro (η-2,5-norbornadiene), oxygen, (-)-sparteine in toluene, Time= 192h, T= 80 °C , Title compound not separated from byproducts Ferreira; Stoltz; Journal of the American Chemical Society; vol. 123; nb. 31; (2001); p. 7725 - 7726 View in Reaxys

58 %

With 3 A molecular sieve, oxygen, (-)-sparteine, palladium dichloro (η-2,5-norbornadiene) in toluene, Time= 192h, T= 80 °C , p= 760Torr Ferreira; Stoltz; Journal of the American Chemical Society; vol. 123; nb. 31; (2001); p. 7725 - 7726 View in Reaxys With immobilized ovalbumin in water, Time= 144h, T= 35 °C , Title compound not separated from byproducts Nagaoka; Kayahara; Wakabayashi; Bioscience, biotechnology, and biochemistry; vol. 65; nb. 3; (2001); p. 634 - 637 View in Reaxys With immobilized pea protein in water, Time= 168h, T= 35 °C , Title compound not separated from byproducts Nagaoka; Kayahara; Wakabayashi; Bioscience, biotechnology, and biochemistry; vol. 65; nb. 3; (2001); p. 634 - 637 View in Reaxys With dichloro bis(acetonitrile) palladium(II), (-)-sparteine in 1,2-dichloro-ethane, T= 70 °C Jensen; Pugsley; Sigman; Journal of the American Chemical Society; vol. 123; nb. 30; (2001); p. 7475 - 7476 View in Reaxys With dichloro bis(acetonitrile) palladium(II), oxygen, (-)-sparteine in 1,2-dichloro-ethane, T= 70 °C , Title compound not separated from byproducts Jensen; Pugsley; Sigman; Journal of the American Chemical Society; vol. 123; nb. 30; (2001); p. 7475 - 7476 View in Reaxys With lyophilized cells of Rhodococcus ruber DSM 44541, acetone in phosphate buffer, Time= 24h, T= 24 °C , pH= 8.0, Title compound not separated from byproducts Stampfer, Wolfgang; Kosjek, Birgit; Faber, Kurt; Kroutil, Wolfgang; Journal of Organic Chemistry; vol. 68; nb. 2; (2003); p. 402 - 406 View in Reaxys With sodium isopropylate, acetone, [RuCl2(PPh3)(ferrocenyloxazolinylphosphine)] in isopropyl alcohol, Time= 0.5h, T= 50 °C Nishibayashi, Yoshiaki; Yamauchi, Akiyoshi; Onodera, Gen; Uemura, Sakae; Journal of Organic Chemistry; vol. 68; nb. 15; (2003); p. 5875 - 5880

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View in Reaxys With 3 A molecular sieve, oxygen, sodium carbonate, Pd((-)-sparteine)2Cl2 in tert-butyl alcohol, Time= 24h, T= 65 °C , Title compound not separated from byproducts Mandal, Sunil K.; Sigman, Matthew S.; Journal of Organic Chemistry; vol. 68; nb. 19; (2003); p. 7535 - 7537 View in Reaxys Stage 1: With MnIII(L-5-t-Bu)(Cl), 1-butyl-2,6-dimethyl-pyridinium; bromide in dichloromethane, water, T= 20 °C Stage 2: With [bis(acetoxy)iodo]benzene in dichloromethane, water, Time= 0.1h, T= 20 °C Cheng, Qigan; Deng, Fanguo; Xia, Chungu; Sun, Wei; Tetrahedron Asymmetry; vol. 19; nb. 20; (2008); p. 2359 - 2362 View in Reaxys With (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.02,7]tridecane, C11H20Br2N2OPd, oxygen, caesium carbonate in chloroform, Time= 60h, T= 20 °C , Molecular sieve, optical yield given as percent ee Breuning, Matthias; Steiner, Melanie; Mehler, Christian; Paasche, Alexander; Hein, David; Journal of Organic Chemistry; vol. 74; nb. 3; (2009); p. 1407 - 1410 View in Reaxys With η-naphthol, C136H102Fe2N4O6 in toluene, Time= 40h, T= 50 °C , optical yield given as percent ee Kunisu, Takashi; Oguma, Takuya; Katsuki, Tsutomu; Journal of the American Chemical Society; vol. 133; nb. 33; (2011); p. 12937 - 12939 View in Reaxys Stage 1: With Br(1-)*C75H107Cl2Mn2N8O4 (1+), potassium bromide in dichloromethane, water, Time= 0.166667h, T= 20 °C Stage 2: With [bis(acetoxy)iodo]benzene in dichloromethane, water, optical yield given as percent ee Li, Chengyong; Zhao, Jiangfeng; Tan, Rong; Peng, Zhigang; Luo, Rongchang; Peng, Ming; Yin, Donghong; Catalysis Communications; vol. 15; nb. 1; (2011); p. 27 - 31 View in Reaxys With bis(1,5-cyclooctadiene)diiridium(I) dichloride, cetyltrimethylammonim bromide, acetone, potassium hydroxide, N,N'bis[o-(diphenylphosphino)benzylidene]-(1S,2S)-diaiminocyclohexane in water, Time= 16h, T= 28 °C , Resolution of racemate, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Zhang, Juanni; Yang, Xiangren; Zhou, Han; Li, Yanyun; Dong, Zhenrong; Gao, Jingxing; Green Chemistry; vol. 14; nb. 5; (2012); p. 1289 - 1292 View in Reaxys 2.5. Typical procedure for the OKR of racemic secondary alcohols General procedure: Racemic secondary alcohols (0.25 mmol), catalyst (1.5 molpercent of substrate), and KBr (0.02 mmol, 0.0024 g) were added to H2O(1.5 mL). The mixture was stirred for 10 min at room temperature, and then PhI(OAc)2 (0.175 mmol, 0.056 g) was added in four equal parts. The reaction progress was monitored by gas chromatography (GC). After achieving the desired oxidation level, the reaction mixture was heated to 40 ηC. The catalyst was precipitated out of the reaction system, washed with diethyl ether(3× 5 mL), dried in a vacuum, and finally recharged with fresh substrate, additive, and oxidant for the next catalytic cycle. The supernatants separated from the reaction system were extractedwith ether three times. The collected organic phase was driedover sodium sulfate and concentrated in a vacuum. The resultantmixture was purified by column chromatography on silica gel athe stationary phase (petroleum ether/ethyl acetate, 90/10). Enantioselectivitywas determined by a Agilent Technologies 6890NGC system equipped with a 19091G-B213 chiral capillary column(30 m×0.32 mm×0.25 m) with an FID. Stage 1: With potassium bromide in water, Time= 0.166667h, T= 25 °C , Resolution of racemate Stage 2: With [bis(acetoxy)iodo]benzene in water, Time= 2h, T= 25 °C , enantioselective reaction Tan, Rong; Dong, Yan; Peng, Ming; Zheng, Weiguo; Yin, Donghong; Applied Catalysis A: General; vol. 458; (2013); p. 1 10 View in Reaxys Typical procedure for the OKR of racemic secondary alcohols with C2-PhI(OAc)2 system General procedure: Typical procedure for the OKR of racemic secondary alcohols with C2-PhI(OAc)2 system To a 5 mL glass reactor substrate (0.25 mmol), catalyst C2 (0.005 mmol, 2 molpercent), CH2Cl2 (0.3 mL) and H2O (0.6 mL) were added and the resulting mass was magnetically stirred for 5 min.

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To the above stirring mass, KBr (4 molpercent) was added at room temperature. The reaction mixture was then cooled to 15 °C and PhI(OAc)2 (0.7 equiv.) was added slowly in small fractions over 15 min and stirring was continued to the specified time. After the completion of the reaction, catalyst was precipitated out by the addition of hexane to the reaction mixture. The recovered catalyst was dried and stored for future use. An aliquot of organic layer was subjected to HPLC analysis to determine enantiomeric excess (ee) of the product. The resulting ketone and enantio-enriched secondary alcohol were separated by silica gel flash chromatography. With [bis(acetoxy)iodo]benzene, C36H50ClMnN2O6, potassium bromide in dichloromethane, water, Time= 0.5h, T= 15 °C Bera, Prasanta Kumar; Maity, Nabin Ch.; Abdi, Sayed H.R.; Khan, Noor-Ul H.; Kureshy, Rukhsana I.; Bajaj, Hari C.; Applied Catalysis A: General; vol. 467; (2013); p. 542 - 551 View in Reaxys 2.2. Catalytic procedure. General procedure: In a typical process, a mixture of (±)-1-phenylethanol (0.122 g, 1 mmol), chiral Mn(III)-salen complex (0.0127 g, 2 molpercent), Br2 (4.1 μL, 8 molpercent), KOAC (0.1962 g, 2 mmol), CH2Cl2 (2.0 mL), and water (4.0 mL) was magnetically stirred in a 10-mL two-necked flask at 20 °C. The oxidant NaClO (0.289 g, 0.80 mmol) was then added slowly within 40 min, and the reaction was monitored by GC/HPLC equipped with a suitable chiral column. With sodium hypochlorite, C38H56ClMnN2O2, bromine, potassium acetate in dichloromethane, water, Time= 0.666667h, T= 20 °C , Kinetics, Mechanism, enantioselective reaction Zhang, Yuecheng; Zhou, Qiao; Ma, Wenchan; Zhao, Jiquan; Catalysis Communications; vol. 45; (2014); p. 114 - 117 View in Reaxys With lyophilised cells of Escherichia coli overexpressing the solvent-tolerant alcohol dehydrogenase from Rhodococcus ruber DSM44541 in aq. buffer, Time= 24h, T= 30 °C , pH= 7.5, Resolution of racemate, Enzymatic reaction Paul, Caroline E.; Lavandera, Ivan; Gotor-Fernandez, Vicente; Kroutil, Wolfgang; Gotor, Vicente; ChemCatChem; vol. 5; nb. 12; (2013); p. 3875 - 3881 View in Reaxys With (R,R)-1,2-di(1-naphthyl)-1,2-ethanediamine, tert.-butylhydroperoxide, potassium carbonate in water, acetonitrile, Time= 5h, T= 29 °C , Molecular sieve Al-Hunaiti, Afnan; Räisänen, Minna; Pihko, Petri; Leskelä, Markku; Repo, Timo; European Journal of Organic Chemistry; vol. 2014; nb. 28; (2014); p. 6141 - 6144 View in Reaxys With NADP in acetone, Time= 22h, T= 50 °C , pH= 8, Resolution of racemate Popłoński, Jarosław; Reiter, Tamara; Kroutil, Wolfgang; ChemCatChem; vol. 10; nb. 4; (2018); p. 763 - 768 View in Reaxys O O Br

Rx-ID: 35618810 View in Reaxys 10/824 Yield 64 %

Conditions & References With tetrabutylammomium bromide, water, cobalt(II) acetate, triphenylphosphine, sodium hydroxide, silicon, Time= 24h, T= 100 °C Gevorgyan, Ashot; Mkrtchyan, Satenik; Grigoryan, Tatevik; Iaroshenko, Viktor O.; ChemPlusChem; vol. 83; nb. 5; (2018); p. 375 - 382 View in Reaxys

38 %

A typical procedure of the electroreductive coupling of aryl bromide1 with catalytic amounts of [OctV2+][Tf2N]2 and Pd species isas follows. Into an undivided cell fitted with a Zn anode(1.5 1 cm2) and a Pt cathode (1.5 1 cm2) was added a DMF(3 mL) solution of 4-bromopropiophenone (1a, 0.25 mmol),[Bu4N+][Tf2N] (0.3 mmol), [OctV2+][Tf2N]2 (0.075 mmol,30 mol percent), and PdCl2(PPh3)2 (0.0125 mmol, 5 mol percent). The wholemixture was electrolyzed at 60 C under constant current(10

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mA) conditions until 2 F/mol—1a of electricity was passed.The reaction mixture was poured into 5percent aq HCl and extractedwith AcOEt. Purification by column chromatography (SiO2, toluene/AcOEt = 10/1) afforded 4,40-dipropanoylbiphenyl (2a) in 94percentyield With 1,1'-dioctyl-4,4'-bipyridinium bis(trifluimide), palladium diacetate, tetrabutylammonium bis(trifluoromethanesulfonyl)imide in N,N-dimethyl-formamide, T= 60 °C , Electrochemical reaction, Solvent, Reagent/catalyst Kuroboshi, Manabu; Shiba, Takuya; Tanaka, Hideo; Tetrahedron Letters; vol. 54; nb. 28; (2013); p. 3666 - 3668 View in Reaxys O

Rx-ID: 36435213 View in Reaxys 11/824 Yield 89 %

Conditions & References With (OTf )2Sc-SO3-Ph-PMO catalyst in water, Time= 12h, T= 10 °C , Mukaiyama Aldol Addition, Mechanism, Reagent/catalyst, Temperature, chemoselective reaction Zhang, Fang; Liang, Chao; Chen, Mingzheng; Guo, Haibing; Jiang, Huangyong; Li, Hexing; Green Chemistry; vol. 15; nb. 10; (2013); p. 2865 - 2871 View in Reaxys

77.3 %

With Yb(OTf)3 immobilized on sodium propylsulphonate and phenyl group co-functionalized magnetic core–mesoporous silica shell composite in water, Time= 16h, T= 20 °C , Green chemistry, Mukaiyama Aldol Addition, Reagent/catalyst Zhang, Fang; Wu, Xiaotao; Liang, Chao; Li, Xiaoyan; Wang, Zhen; Li, Hexing; Green Chemistry; vol. 16; nb. 8; (2014); p. 3768 - 3777 View in Reaxys With ytterbium triflate ordered mesoporous polymer in water, Time= 12h, T= 20 °C , Mukaiyama Aldol Addition, Catalytic behavior, Reagent/catalyst Zhang, Fang; Liang, Chao; Wang, Zhen; Li, Hexing; ChemCatChem; vol. 10; nb. 4; (2018); p. 818 - 824 View in Reaxys O O B

Rx-ID: 47638202 View in Reaxys 12/824 Yield 97 %

Conditions & References With bis(1,5-cyclooctadiene)nickel (0), caesium carbonate, tricyclohexylphosphine in hexane, toluene, Time= 16h, T= 60 °C , Sealed tube, Glovebox, Suzuki-Miyaura Coupling, chemoselective reaction Chatupheeraphat, Adisak; Liao, Hsuan-Hung; Srimontree, Watchara; Guo, Lin; Minenkov, Yury; Poater, Albert; Cavallo, Luigi; Rueping, Magnus; Journal of the American Chemical Society; vol. 140; nb. 10; (2018); p. 3724 - 3735 View in Reaxys

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O O

Rx-ID: 47999816 View in Reaxys 13/824 Yield

Conditions & References

35 %Chromat., 22 %Chromat., 11 %Chromat., 32 %Chromat.

3.2. General Procedure for the Isomerization of Epoxides1 Using LDA under MW Irradiations General procedure: A solution of LDA (1 mmol) in organic solvent (pentane,THF, DEE, DME or 1,4-dioxane, 0.5 M) was prepared at−78° C (in the case of 1,4-dioxane, the temperature was notbelow 20° C in order to avoid the solvent freezing) from nBuLi (1.6 M solution in hexanes, 1 mmol) and diisopropylamine(1 mmol) in a vessel for MW reactions under nitrogenatmosphere. After 30’, the epoxide 1 (0.5 mmol) wasadded and the resulting reaction mixture was placed in a microwaveoven. The solution was, then, diluted in Et2O andH2O. The two phases were separated and the aqueous portionwas extracted with ether. The combined organic layers were,subsequently, washed with H2O and brine, anhydride overNa2SO4, filtered and concentrated in vacuum to afford theisomerization products, which were furthermore analyzed byGC/MS. With n-butyllithium, diisopropylamine in hexane, pentane, Reflux, Inert atmosphere, Schlenk technique Consiglio, Gabriella Barozzino; Mordini, Alessandro; Letters in Organic Chemistry; vol. 15; nb. 5; (2018); p. 447 - 454 View in Reaxys O

Rx-ID: 47999826 View in Reaxys 14/824 Yield

Conditions & References Reaction Steps: 2 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C / Inert atmosphere; Schlenk technique 2: n-butyllithium; diisopropylamine / hexane; pentane / Reflux; Inert atmosphere; Schlenk technique With n-butyllithium, diisopropylamine, 3-chloro-benzenecarboperoxoic acid in hexane, dichloromethane, pentane Consiglio, Gabriella Barozzino; Mordini, Alessandro; Letters in Organic Chemistry; vol. 15; nb. 5; (2018); p. 447 - 454 View in Reaxys O O

N O

H 2N

S NH

Rx-ID: 48010896 View in Reaxys 15/824 Yield 75 %

Conditions & References With 1,10-Phenanthroline, water, palladium diacetate in N,N-dimethyl-formamide, Time= 6h, T= 100 °C , p= 760.051Torr Meng, Mengting; Yang, Liangfeng; Cheng, Kai; Qi, Chenze; Journal of Organic Chemistry; vol. 83; nb. 6; (2018); p. 3275 3284 View in Reaxys O O

Rx-ID: 2007968 View in Reaxys 16/824 Yield 32 %, 60 %

Conditions & References 4. Typical procedure for oxidation of alkylbenzenes and toluene

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General procedure: Ethylbenzene (3a) (0.0531 g, 0.5 mmol), K2S2O8 (0.2703 g, 1.0 mmol), pyridine (0.0158 g, 0.2 mmol) and CH3CN (1.0 mL) were added to an oven-dried pressure vessel with a magnetic stir bar. Then the pressure vessel was filled with dioxygen and the reaction mixture was stirred at 80 °C for 16 hours (oil bath). After the completion of the reaction, the solvent was evaporated and the reaction mixture was purified with column chromatography (eluenet: ethyl acetate/PE = 1/10) to give acetophenone (4a) (0.0535 g yield 89percent). With pyridine, dipotassium peroxodisulfate, oxygen in acetonitrile, Time= 16h, T= 80 °C , p= 760.051Torr , Green chemistry Hu, Yixin; Zhou, Lihong; Lu, Wenjun; Synthesis (Germany); vol. 49; nb. 17; (2017); p. 4007 - 4016 View in Reaxys 12.2 % Chromat., 74.9 % Chromat.

With oxygen, MnBr2(pyridine)2, dibromobis(pyridine)cobalt(II) in acetic acid, Time= 0.833333h, T= 140 °C , p= 7500.6Torr , other time, Product distribution Hronec, Milan; Holotik, Stefan; Ilavsky, Jan; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 3; (1980); p. 880 - 887 View in Reaxys 7 : 7. Oxidation of Propylbenzene In a 50 cm3 round bottomed flask, equipped with a magnetic stirrer and reflux condenser, was added propylbenzene (1.21 g, 10 mmol) and [bmim] [OMs] (1.0 g). 67percent Nitric acid (0.45 g, 5 mmol) was cautiously added and the mixture heated under reflux. After 54, 80 hours the mixture was analysed by gas chromatography and found to give 15percent conversion. Three products were identified (GCMS) as: propiophenone, benzoic acid and 3-phenylpentane in the ratio (2:1:trace). With nitric acid, 1-n-butyl-3-methylimidazolium methanesulfonate in water, Time= 80h, Heating / reflux Patent; Earle, Martyn John; Katdare, Suhas Prabhakar; US2004/15009; (2004); (A1) English View in Reaxys O OH

Rx-ID: 8940491 View in Reaxys 17/824 Yield 90 % Chromat., 8 % Chromat.

Conditions & References With Sphingomonas paucimobilis NCIMB 8195 in water, N,N-dimethyl-formamide, Time= 120h Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys 3 :An 8 ml glass vial was charged with 1.2mg peptoid (7mers, lxlηηnol), 0.25 ml CH2Cl2, 0.125 ml of 0.5M KBr in water and lxlηηnol substrate (alcohol), placed in an ice bath and cooled to 0°C under stirring. The reaction started with the addition of 0.310 ml 0.5M NaOCl solution [1 equivalent of 1.8M NaOCl (that contains 10-13percent Cl) and 2.6 equivalents of water]. After two hours, 1 ml CH2Cl2 was added, the aqueous layer was separated and a sample from the CH2Cl2 solution was analyzed by GC. With sodium hypochlorite, potassium bromide, H-NtempoNspeNpm(Nspe)2NpmNspe-NH2 in dichloromethane, water, Time= 2h, T= 0 °C , Product distribution / selectivity Patent; NEW YORK UNIVERSITY SCHOOL OF MEDICINE; WO2009/139922; (2009); (A2) English View in Reaxys Typical procedure for the OKR of racemic secondary alcohols with C2-NBS system General procedure: Typical procedure for the OKR of racemic secondary alcohols with C2-NBS system To a 5 mL glass reactor substrate (0.25 mmol), catalyst C2 (0.0037 mmol, 1.5 molpercent), KOAc (0.8 equiv.), CH2Cl2 (0.5 mL) and H2O (1 mL) were added and the resulting mass was magnetically stirred for 5 min. To the stirring mass NBS (0.7 equiv.) was added slowly in small fractions over 20 min and stirring was continued for the specified time. After the completion of the reaction, catalyst was precipitated out by the addition of hexane to the reaction mixture. The recovered catalyst was dried and stored for further use. An aliquot of organic layer was subjected to HPLC analysis to determine enantiomeric excess (ee) of the product. The resulting ketone and enantio-enriched secondary alcohol were separated by silica gel flash chromatography.

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With N-Bromosuccinimide, C36H50ClMnN2O6, potassium acetate in dichloromethane, water, T= 20 °C Bera, Prasanta Kumar; Maity, Nabin Ch.; Abdi, Sayed H.R.; Khan, Noor-Ul H.; Kureshy, Rukhsana I.; Bajaj, Hari C.; Applied Catalysis A: General; vol. 467; (2013); p. 542 - 551 View in Reaxys With (R,R)-1,2-di(1-naphthyl)-1,2-ethanediamine, tert.-butylhydroperoxide, potassium carbonate in decane, dichloromethane, Time= 20h, T= 29 °C , Molecular sieve Al-Hunaiti, Afnan; Räisänen, Minna; Pihko, Petri; Leskelä, Markku; Repo, Timo; European Journal of Organic Chemistry; vol. 2014; nb. 28; (2014); p. 6141 - 6144 View in Reaxys With Fusarium proliferatum mycelia in aq. phosphate buffer, pH= 7.2, Microbiological reaction, Resolution of racemate, enantioselective reaction Jadhav, Dipesh D.; Patil, Harshal S.; Chaya, Patil S.; Thulasiram, Hirekodathakallu V.; Tetrahedron Letters; vol. 57; nb. 41; (2016); p. 4563 - 4567 View in Reaxys With sulfuric acid, MnII((1R,2R)-N,N'-dimethyl-N,N'-bis((R)-(3,5-di-tert-butylphenyl)-2-pyridinylmethyl)cyclohexane-1,2-diamine)(OTf)2, dihydrogen peroxide in water, acetonitrile, Time= 1h, T= 0 °C , Inert atmosphere, Schlenk technique Miao, Chengxia; Li, Xiao-Xi; Lee, Yong-Min; Xia, Chungu; Wang, Yong; Nam, Wonwoo; Sun, Wei; Chemical Science; vol. 8; nb. 11; (2017); p. 7476 - 7482 View in Reaxys O HO

Rx-ID: 11207938 View in Reaxys 18/824 Yield 7 %, 93 %

Conditions & References 2.3. General procedure for the 1-phenyl-2-propene-1-ol allylic isomerization in THF General procedure: A solution containing 6.4 × 10−3mmol of precatalyst and0.13 mmol of substrate (20 equiv.) in 2 mL of THF was transferred into a 5 mL glass vial which was then placed under argon into a stainless steel autoclave equipped with a magnetic stirring bar. The reaction vessel was pressurized with H2 to 30 bar and stirred for the desired time at room temperature. Then pressure was released andthe reaction vessel was stirred for the desired time at controlledtemperature under a dihydrogen atmosphere at 1 bar. Alterna-tively, after venting the H2pressure used for the catalyst activation,the residual H2was purged with argon by continuous flushingbefore continuing the reaction. The pure products were obtainedby chromatography of the reaction mixture on silica gel using dichloromethane as eluent and then analyzed by NMR spectrosopyand chiral GC for the determination of the yields and enantiomeric excesses. With C35H41FePRhS, hydrogen, sodium methylate in tetrahydrofuran, Time= 16h, T= 82 °C , p= 22502.3Torr , Autoclave, Inert atmosphere Titova, Ekaterina M.; Rahaman, S.M. Wahidur; Shubina, Elena S.; Poli, Rinaldo; Belkova, Natalia V.; Manoury, Eric; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 376 - 380 View in Reaxys

5 % Spectr., With triethylamine, 10 wt. % palladium on activated carbon in toluene, Time= 3h, T= 150 °C 91 % Coquerel, Yoann; Bremond, Paul; Rodriguez, Jean; Journal of Organometallic Chemistry; vol. 692; nb. 22; (2007); p. 4805 Spectr. 4808 View in Reaxys 82 %Chromat.

With {(η3:η2:η3-C12H18)RuCl2}, water, sodium formate, Time= 24h, T= 100 °C , Inert atmosphere Cadierno, Victorio; Crochet, Pascale; Francos, Javier; Garcia-Garrido, Sergio E.; Gimeno, Jose; Nebra, Noel; Green Chemistry; vol. 11; nb. 12; (2009); p. 1992 - 2000 View in Reaxys

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O H

Rx-ID: 21547510 View in Reaxys 19/824 Yield

Conditions & References Reaction Steps: 2 2: 2<HRh(CO)(PPh3)>,3e<Me3SiC(CH2)C(O)Ph> / benzene / 20 h / 105 °C / in sealed tube With 2<HRh(CO)(PPh3)>, 2-trimethylsilyl-1-phenyl-2-propen-1-one in benzene Matsuda, Isamu; Sato, Susumu; Izumi, Yusuke; Tetrahedron Letters; vol. 24; nb. 27; (1983); p. 2787 - 2790 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 2 h / -10 °C / Inert atmosphere 2: benzaldehyde; tris(triphenylphosphine)ruthenium(II) chloride; sodium acetate / 1,2-dichloro-ethane / 4 h / 90 °C / Schlenk technique; Inert atmosphere With tris(triphenylphosphine)ruthenium(II) chloride, sodium acetate, benzaldehyde in tetrahydrofuran, 1,2-dichloro-ethane Ren, Kai; Hu, Bei; Zhao, Mengmeng; Tu, Yahui; Xie, Xiaomin; Zhang, Zhaoguo; Journal of Organic Chemistry; vol. 79; nb. 5; (2014); p. 2170 - 2177 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; t-butyl [(S)-1-((S)-2-hydroxypropylcarbamoyl)ethyl]carbamate; lithium chloride; potassium tert-butylate / toluene / 3 h / 40 °C / Inert atmosphere With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, potassium tert-butylate, lithium chloride, t-butyl [(S)-1-((S)-2-hydroxypropylcarbamoyl)ethyl]carbamate in tetrahydrofuran, toluene Slagbrand, Tove; Lundberg, Helena; Adolfsson, Hans; Chemistry - A European Journal; vol. 20; nb. 49; (2014); p. 16102 16106 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 0 °C 2: Jones reagent / acetone / 0.5 h / 0 - 20 °C With Jones reagent in tetrahydrofuran, acetone Li, Chengliang; Jin, Tao; Zhang, Xinglu; Li, Chunju; Jia, Xueshun; Li, Jian; Organic Letters; vol. 18; nb. 8; (2016); p. 1916 - 1919 View in Reaxys Reaction Steps: 3 1.1: lithium diisopropyl amide / tetrahydrofuran / 2.5 h / -78 °C 1.2: 2.5 h / -78 °C 2.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 3.1: nano-Pd1Ni4 /MIL-100(Fe) / water / 6 h / 180 °C / Inert atmosphere With sodium tetrahydroborate, lithium diisopropyl amide in tetrahydrofuran, water Zhang, Jia-Wei; Lu, Guo-Ping; Cai, Chun; Green Chemistry; vol. 19; nb. 19; (2017); p. 4538 - 4543 View in Reaxys O

Rx-ID: 34265976 View in Reaxys 20/824

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Yield

Conditions & References

92 %

With sodium hydride in diethyl ether, Time= 1h, T= 25 °C Shipilovskikh, Sergei A.; Rubtsov, Aleksandr E.; Malkov, Andrei V.; Organic Letters; vol. 19; nb. 24; (2017); p. 6760 - 6762 View in Reaxys

59 %

With tetrafluoroboric acid, iodosylbenzene in 1,4-dioxane, water, Time= 108h, T= 20 °C , Inert atmosphere Havare, Nizam; Plattner, Dietmar A.; Organic Letters; vol. 14; nb. 19; (2012); p. 5078 - 5081,4 View in Reaxys

O OH

H HO

Rx-ID: 39087131 View in Reaxys 21/824 Yield

Conditions & References

66 %

2.3. General procedure for the 1-phenyl-2-propene-1-ol allylic isomerization in THF General procedure: A solution containing 6.4 × 10−3mmol of precatalyst and0.13 mmol of substrate (20 equiv.) in 2 mL of THF was transferred into a 5 mL glass vial which was then placed under argon into a stainless steel autoclave equipped with a magnetic stirring bar. The reaction vessel was pressurized with H2 to 30 bar and stirred for the desired time at room temperature. Then pressure was released andthe reaction vessel was stirred for the desired time at controlledtemperature under a dihydrogen atmosphere at 1 bar. Alterna-tively, after venting the H2pressure used for the catalyst activation,the residual H2was purged with argon by continuous flushingbefore continuing the reaction. The pure products were obtainedby chromatography of the reaction mixture on silica gel using dichloromethane as eluent and then analyzed by NMR spectrosopyand chiral GC for the determination of the yields and enantiomeric excesses. With C34H41ClFePRhS, hydrogen, sodium methylate in tetrahydrofuran, Time= 16h, T= 82 °C , p= 22502.3Torr , Autoclave, Inert atmosphere Titova, Ekaterina M.; Rahaman, S.M. Wahidur; Shubina, Elena S.; Poli, Rinaldo; Belkova, Natalia V.; Manoury, Eric; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 376 - 380 View in Reaxys With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, potassium tert-butylate, lithium chloride, t-butyl [(S)-1-((S)-2-hydroxypropylcarbamoyl)ethyl]carbamate in tetrahydrofuran, ethanol, Time= 3h, T= 40 °C , Inert atmosphere, Concentration, enantioselective reaction Slagbrand, Tove; Lundberg, Helena; Adolfsson, Hans; Chemistry - A European Journal; vol. 20; nb. 49; (2014); p. 16102 16106 View in Reaxys O

H 2N

Rx-ID: 39863416 View in Reaxys 22/824 Yield

Conditions & References

25 %Spectr. With 4-tert-butyl-5-methoxy-1,2-benzoquinone, oxygen in acetonitrile, Time= 48h, T= 60 °C , Schlenk technique Qin, Yan; Zhang, Long; Lv, Jian; Luo, Sanzhong; Cheng, Jin-Pei; Organic Letters; vol. 17; nb. 6; (2015); p. 1469 - 1472 View in Reaxys Reaction Steps: 3 1: N-chloro-succinimide / 0.17 h / 20 °C / Milling 2: triethylamine / 0.17 h / 20 °C / Milling

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3: water; hydrogenchloride / tetrahydrofuran / 2 h / 20 °C With hydrogenchloride, N-chloro-succinimide, water, triethylamine in tetrahydrofuran Gaspa, Silvia; Porcheddu, Andrea; Valentoni, Antonio; Garroni, Sebastiano; Enzo, Stefano; De Luca, Lidia; European Journal of Organic Chemistry; vol. 2017; nb. 37; (2017); p. 5519 - 5526 View in Reaxys O

O O

Rx-ID: 44456676 View in Reaxys 23/824 Yield

Conditions & References in methanol, T= 20 °C , Irradiation Griesbeck, Axel G.; Porschen, Björn; Kropf, Christian; Landes, Agnieszka; Hinze, Olga; Huchel, Ursula; Gerke, Thomas; Synthesis (Germany); vol. 49; nb. 3; (2017); p. 539 - 553; Art.No: SS-2016-E0569-FA View in Reaxys O

Rx-ID: 44461503 View in Reaxys 24/824 Yield

Conditions & References

73 %Chromat.

With N-Methyldicyclohexylamine, chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II) in toluene, Time= 3h, T= 100 °C , Heck Reaction Orr, Robert K.; Campeau, Louis-Charles; Chobanian, Harry R.; McCabe Dunn, Jamie M.; Pio, Barbara; Plummer, Christopher W.; Nolting, Andrew; Ruck, Rebecca T.; Synthesis (Germany); vol. 49; nb. 3; (2017); p. 657 - 666; Art.No: SS-2016-M0494-OP View in Reaxys O

HO B

O HO

Rx-ID: 45566986 View in Reaxys 25/824 Yield 74 %

Conditions & References With potassium phosphate, [(1,3-bis-2',6'-diisopropylphenylimidazol-2-ylidene)PdCl(η-cinnamyl)], water in tetrahydrofuran, Time= 2h, T= 90 °C , Inert atmosphere, Sealed tube, Schlenk technique, Suzuki-Miyaura Coupling Halima, Taoufik Ben; Zhang, Wanying; Yalaoui, Imane; Hong, Xin; Yang, Yun-Fang; Houk, Kendall N.; Newman, Stephen G.; Journal of the American Chemical Society; vol. 139; nb. 3; (2017); p. 1311 - 1318 View in Reaxys

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O HO

Rx-ID: 45640258 View in Reaxys 26/824 Yield 100 %

Conditions & References Oxidation of 4-t-butylcyclohexanaol General procedure: O.1 mole of 4-t-butylcyclohexanol (ACROS) was weighed and placed in a 50 mL Erlenmeyer flask with stir bar and 10 mL ethyl acetate (Fisher). 1.0 g trichloroisocyanuric acid (Leslie’s Swimming Pool Supplies) was weighed into a 30 mL beaker and dissolved in 10 mL ethyl acetate. 1.0 mL (0.12 mol) pyridine (Aldrich) was delivered to the alcohol mixture by pipet. The TCICA solution was transferred to a dropping funnel and added dropwise to the stirring alcohol solution. Following addition, stirring was continued for 20 minutes and the mixture was filtered. The filtrate was washed with 10 mL 1 M HCl, 10 mL 5percent NaHCO3, and 5 mL saturated NaCl. The organic layer was dried over MgSO4, a GC sample removed, filtered and evaporated to dryness. Yield 1.50 g (100percent), nmr attached. With picoline, trichloroisocyanuric acid in ethyl acetate, Time= 0.333333h, T= 20 °C , Reagent/catalyst, Time Dip, Irene; Gethers, Christina; Rice, Tonya; Straub, Thomas S.; Tetrahedron Letters; vol. 58; nb. 28; (2017); p. 2720 - 2722 View in Reaxys

O O HO

Rx-ID: 45726980 View in Reaxys 27/824 Yield 15 %, 70 %

Conditions & References With potassium tert-butylate in tetrahydrofuran, Time= 6h, T= 80 °C , Schlenk technique, Inert atmosphere, Reagent/catalyst Suchand, Basuli; Satyanarayana, Gedu; European Journal of Organic Chemistry; vol. 2017; nb. 26; (2017); p. 3886 - 3895 View in Reaxys

48 %, 10 %

With potassium tert-butylate in tetrahydrofuran, Time= 8h, T= 80 °C , Schlenk technique, Inert atmosphere, Solvent Suchand, Basuli; Satyanarayana, Gedu; European Journal of Organic Chemistry; vol. 2017; nb. 26; (2017); p. 3886 - 3895 View in Reaxys

Cl Mg

H 2N

Rx-ID: 45950890 View in Reaxys 28/824 Yield 88 %, 12 %

Conditions & References Stage 1: With methanol, water in dibutyl ether, Time= 0.0166667h, T= 20 °C , Inert atmosphere, Schlenk technique Stage 2: With methanol, water in dibutyl ether, Time= 0.0833333h, T= 20 °C , Inert atmosphere, Schlenk technique Dilauro, Giuseppe; Dell'Aera, Marzia; Vitale, Paola; Capriati, Vito; Perna, Filippo Maria; Angewandte Chemie - International Edition; vol. 56; nb. 34; (2017); p. 10200 - 10203; Angew. Chem.; vol. 129; nb. 34; (2017); p. 10334 - 10337,4 View in Reaxys

83 %

Stage 1: With water in dibutyl ether, Time= 0.0166667h, T= 20 °C , Inert atmosphere, Schlenk technique Stage 2: With water in dibutyl ether, Time= 0.0833333h, T= 20 °C , Inert atmosphere, Schlenk technique, chemoselective reaction

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Dilauro, Giuseppe; Dell'Aera, Marzia; Vitale, Paola; Capriati, Vito; Perna, Filippo Maria; Angewandte Chemie - International Edition; vol. 56; nb. 34; (2017); p. 10200 - 10203; Angew. Chem.; vol. 129; nb. 34; (2017); p. 10334 - 10337,4 View in Reaxys

O H 2N

Rx-ID: 45950899 View in Reaxys 29/824 Yield

Conditions & References

87 %

Stage 1: With water in hexane, Time= 0.0166667h, T= 20 °C , Inert atmosphere, Schlenk technique Stage 2: With water in hexane, Time= 0.0833333h, T= 20 °C , Inert atmosphere, Schlenk technique, chemoselective reaction Dilauro, Giuseppe; Dell'Aera, Marzia; Vitale, Paola; Capriati, Vito; Perna, Filippo Maria; Angewandte Chemie - International Edition; vol. 56; nb. 34; (2017); p. 10200 - 10203; Angew. Chem.; vol. 129; nb. 34; (2017); p. 10334 - 10337,4 View in Reaxys O

N Cl

Rx-ID: 46364965 View in Reaxys 30/824 Yield

Conditions & References Reaction Steps: 2 1: triethylamine / 0.17 h / 20 °C / Milling 2: water; hydrogenchloride / tetrahydrofuran / 2 h / 20 °C With hydrogenchloride, water, triethylamine in tetrahydrofuran Gaspa, Silvia; Porcheddu, Andrea; Valentoni, Antonio; Garroni, Sebastiano; Enzo, Stefano; De Luca, Lidia; European Journal of Organic Chemistry; vol. 2017; nb. 37; (2017); p. 5519 - 5526 View in Reaxys Cl

Rx-ID: 46364993 View in Reaxys 31/824 Yield 0.149 g

Conditions & References With hydrogenchloride, water in tetrahydrofuran, Time= 2h, T= 20 °C Gaspa, Silvia; Porcheddu, Andrea; Valentoni, Antonio; Garroni, Sebastiano; Enzo, Stefano; De Luca, Lidia; European Journal of Organic Chemistry; vol. 2017; nb. 37; (2017); p. 5519 - 5526 View in Reaxys

O HO

O O

Rx-ID: 46381342 View in Reaxys 32/824

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Yield

Conditions & References Reaction Steps: 2 1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 2: nano-Pd1Ni4 /MIL-100(Fe) / water / 6 h / 180 °C / Inert atmosphere With sodium tetrahydroborate in tetrahydrofuran, water Zhang, Jia-Wei; Lu, Guo-Ping; Cai, Chun; Green Chemistry; vol. 19; nb. 19; (2017); p. 4538 - 4543 View in Reaxys

O O

Rx-ID: 46381348 View in Reaxys 33/824 Yield

Conditions & References With nano-Pd1Ni4 /MIL-100(Fe) in water, Time= 6h, T= 180 °C , Inert atmosphere Zhang, Jia-Wei; Lu, Guo-Ping; Cai, Chun; Green Chemistry; vol. 19; nb. 19; (2017); p. 4538 - 4543 View in Reaxys O

HO O

Rx-ID: 46517677 View in Reaxys 34/824 Yield

Conditions & References

30 %Chromat., 24 %Chromat.

With potassium hydroxide, Time= 24h, T= 120 °C

6 %Chromat., 90 %Chromat.

With potassium hydroxide, Time= 24h, T= 120 °C

Jiang, Lei; Guo, Fang; Shi, Zhenghai; Li, Yang; Hou, Zhaomin; ChemCatChem; vol. 9; nb. 20; (2017); p. 3827 - 3832 View in Reaxys

Jiang, Lei; Guo, Fang; Shi, Zhenghai; Li, Yang; Hou, Zhaomin; ChemCatChem; vol. 9; nb. 20; (2017); p. 3827 - 3832 View in Reaxys O

HO O

Rx-ID: 46517678 View in Reaxys 35/824 Yield 17 %Chromat.

Conditions & References With potassium hydroxide, Time= 24h, T= 90 °C , Reagent/catalyst, Temperature Jiang, Lei; Guo, Fang; Shi, Zhenghai; Li, Yang; Hou, Zhaomin; ChemCatChem; vol. 9; nb. 20; (2017); p. 3827 - 3832 View in Reaxys O

Rx-ID: 46564344 View in Reaxys 36/824

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Yield

Conditions & References With 18-crown-6 ether, potassium hydroxide in toluene, Time= 24h, T= 70 °C Zhang, Bing; Wang, Huai-Wei; Kang, Yan-Shang; Zhang, Ping; Xu, Hua-Jin; Lu, Yi; Sun, Wei-Yin; Organic Letters; vol. 19; nb. 21; (2017); p. 5940 - 5943 View in Reaxys

O HO

OH H HO

Rx-ID: 46594807 View in Reaxys 37/824 Yield

Conditions & References With ferredoxin reductase, ferredoxin, P450 monooxygenase CYP101B1 from a Novosphingobium bacterium, H85F mutant, NADH, bovine liver catalase in aq. buffer, T= 30 °C , pH= 7.4, Enzymatic reaction, Kinetics, Reagent/catalyst, enantioselective reaction Sarkar, Md. Raihan; Lee, Joel H. Z.; Bell, Stephen G.; ChemBioChem; vol. 18; nb. 21; (2017); p. 2119 - 2128 View in Reaxys O

Rx-ID: 46735736 View in Reaxys 38/824 Yield 7 %Chromat., 31 %Chromat., 54 %Chromat., 79 %Chromat.

Conditions & References With hydrogen in methanol, Time= 6h, T= 180 °C , p= 7500.75Torr , High pressure Zhang, Chaofeng; Li, Hongji; Lu, Jianmin; Zhang, Xiaochen; Macarthur, Katherine E.; Heggen, Marc; Wang, Feng; ACS Catalysis; vol. 7; nb. 5; (2017); p. 3419 - 3429 View in Reaxys

O OH H

Rx-ID: 46906670 View in Reaxys 39/824 Yield

Conditions & References With methanol, recombinant evolved peroxygenase from Agrocybe aegerita, oxygen in aq. phosphate buffer, Time= 70h, T= 30 °C , pH= 7, Irradiation, Enzymatic reaction, Catalytic behavior, Overall yield = 72 percentChromat. Zhang, Wuyuan; Burek, Bastien O.; Fernández-Fueyo, Elena; Alcalde, Miguel; Bloh, Jonathan Z.; Hollmann, Frank; Angewandte Chemie - International Edition; vol. 56; nb. 48; (2017); p. 15451 - 15455; Angew. Chem.; vol. 129; nb. 48; (2017); p. 15654 - 15658,5 View in Reaxys

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O O

Rx-ID: 46923031 View in Reaxys 40/824 Yield

Conditions & References Reaction Steps: 2 1.1: methyllithium / diethyl ether; tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 1.2: -78 - 20 °C / 750.08 Torr / Inert atmosphere; Schlenk technique 2.1: diethyl ether; tetrahydrofuran / 20 h / -20 - 20 °C / Inert atmosphere; Schlenk technique 2.2: 20 °C / Inert atmosphere; Schlenk technique With methyllithium in tetrahydrofuran, diethyl ether Berton, Mateo; Mello, Rossella; Williard, Paul G.; González-Núñez, María Elena; Journal of the American Chemical Society; vol. 139; nb. 48; (2017); p. 17414 - 17420 View in Reaxys O

O–

Li+

Rx-ID: 46923039 View in Reaxys 41/824 Yield

Conditions & References Stage 1: in tetrahydrofuran, diethyl ether, Time= 20h, T= -20 - 20 °C , Inert atmosphere, Schlenk technique Stage 2: With hydrogenchloride, water in tetrahydrofuran, diethyl ether, T= 20 °C , Inert atmosphere, Schlenk technique Berton, Mateo; Mello, Rossella; Williard, Paul G.; González-Núñez, María Elena; Journal of the American Chemical Society; vol. 139; nb. 48; (2017); p. 17414 - 17420 View in Reaxys O

O–

Li+

ILi

Rx-ID: 46923043 View in Reaxys 42/824 Yield

Conditions & References

72 %Chromat.

Stage 1: With 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, diethyl ether, Time= 0.5h, T= 20 °C , Inert atmosphere, Schlenk technique Stage 2: in tetrahydrofuran, diethyl ether, Time= 15h, T= 20 °C , Inert atmosphere, Schlenk technique Stage 3: With hydrogenchloride, water in tetrahydrofuran, diethyl ether Berton, Mateo; Mello, Rossella; Williard, Paul G.; González-Núñez, María Elena; Journal of the American Chemical Society; vol. 139; nb. 48; (2017); p. 17414 - 17420 View in Reaxys O

Rx-ID: 667354 View in Reaxys 43/824

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Yield 96 %

Conditions & References With decaborane, 10 wt. % palladium on activated carbon in methanol, Time= 3h, T= 20 °C Seung Hwan Lee; Yeon Joo Jung; Young Jin Cho; Choon-Ock Maing Yoon; Han-Joon Hwang; Yoon; Synthetic Communications; vol. 31; nb. 15; (2001); p. 2251 - 2254 View in Reaxys

94 %

With sodium dithionite in water, N,N-dimethyl-formamide, Time= 5h, Ambient temperature Chung, Sung-Kee; Hu, Qing-Yu; Synthetic Communications; vol. 12; nb. 4; (1982); p. 261 - 266 View in Reaxys

93 %

With water, monomethylgallium di-iodide in tetrahydrofuran, N,N-dimethyl-formamide, Time= 4h, Ambient temperature Han, Ying; Huang, Yao-Zeng; Tetrahedron Letters; vol. 39; nb. 42; (1998); p. 7751 - 7754 View in Reaxys

92 %

With bismuth, ammonium fluoride-hydrogen fluoride in water, Time= 4h, T= 20 °C Lee, Yoon Joo; Chan, Tak Hang; Canadian Journal of Chemistry; vol. 82; nb. 2; (2004); p. 71 - 74 View in Reaxys

91.9 %

With bismuth(III) chloride, sodium tetrahydroborate in tetrahydrofuran, Time= 4h, Ambient temperature Ren, Ping-Da; Jin, Qi-Hui; Yao, Zi-Peng; Synthetic Communications; vol. 27; nb. 15; (1997); p. 2577 - 2581 View in Reaxys

87 %

With potassium fluoride, bis(triphenylstannyl)tellurium in acetonitrile, Time= 5h, Ambient temperature Li; Harpp, David N.; Tetrahedron Letters; vol. 32; nb. 12; (1991); p. 1545 - 1548 View in Reaxys

87 %

With sodium tetrahydroborate, antimony(III) bromide in tetrahydrofuran, dimethyl sulfoxide, T= 0 - 22 °C Sayama, Shinsei; Inamura, Yutaka; Chemistry Letters; nb. 8; (1996); p. 633 - 634 View in Reaxys

86 %

With triphenyl phosphite, sodium hydrogencarbonate, (BrBu2Te)2O in water, N,N-dimethyl-formamide, Time= 3h, T= 80 °C Huang, Zheng-Zheng; Tang, Yong; Journal of Organic Chemistry; vol. 67; nb. 15; (2002); p. 5320 - 5326 View in Reaxys

85 %

With bis(cyclopentadienyl)titanium dichloride, samarium in tetrahydrofuran, Time= 1h, Ambient temperature Zhang; Yu; Bao; Synthetic Communications; vol. 25; nb. 12; (1995); p. 1825 - 1830 View in Reaxys

85 %

With water, 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate, Time= 0.0666667h, T= 125 °C , p= 2585.74Torr , microwave irradiation Ranu, Brindaban C.; Chattopadhyay, Kalicharan; Jana, Ranjan; Tetrahedron; vol. 63; nb. 1; (2007); p. 155 - 159 View in Reaxys

83.8 %

With indium, acetic acid in methanol, Time= 1h, T= 20 °C Lee, Seung Hwan; Cho, Min Young; Nam, Mi Hye; Park, Young Sang; Yoo, Byung Woo; Lee, Chi-Woo; Yoon, Cheol Min; Synthetic Communications; vol. 35; nb. 10; (2005); p. 1335 - 1341 View in Reaxys

81 %

With N,N,N,N,-tetramethylethylenediamine, diisobutylaluminium hydride, tin(ll) chloride in tetrahydrofuran, toluene, Time= 0.166667h, T= -78 °C Oriyama, Takeshi; Mukaiyama, Teruaki; Chemistry Letters; (1984); p. 2069 - 2070 View in Reaxys

81 %

With rongalite in ethanol, Time= 1h, Heating Harris, Alan R.; Synthetic Communications; vol. 17; nb. 13; (1987); p. 1587 - 1592

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View in Reaxys 78 %

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, meso-5,10,15,20-tetraphenyl-21-monothiaporphyrin, N-ethylN,N-diisopropylamine in N,N-dimethyl-formamide, Time= 18h, T= 22 °C , Irradiation Lee, Jingyu; Papatzimas, James W.; Bromby, Ashley D.; Gorobets, Evgueni; Derksen, Darren J.; RSC Advances; vol. 6; nb. 64; (2016); p. 59269 - 59272 View in Reaxys

65 %

With potassium fluoride, 1,3-di-tert-butyl-1,1,3,3-tetramethyldisilatellurane in acetonitrile, Time= 24h, Ambient temperature Schultz, Erwin K. V.; Harpp, David N.; Synthesis; nb. 8; (1998); p. 1137 - 1140 View in Reaxys

50 %

With ammonium chloride, zinc in ethanol, Time= 0.00833333h, T= 80 °C , microwave irradiation Li, Jian; Ye, Deju; Liu, Hong; Luo, Xiaoming; Jiang, Hualiang; Synthetic Communications; vol. 38; nb. 4; (2008); p. 567 575 View in Reaxys With potassium carbonate Kohler; American Chemical Journal; vol. 41; (1909); p. 425 View in Reaxys With methanol, triphenylantimony, 1.) CD3CN, 70 deg C, 3 d, Yield given. Multistep reaction Akiba, Kin-ya; Shimizu, Akiyoshi; Ohnari, Hideyuki; Ohkata, Katsuo; Tetrahedron Letters; vol. 26; nb. 27; (1985); p. 3211 - 3214 View in Reaxys in methanol, Irradiation, Yield given Izawa, Yasuji; Watoh, Yasushi; Tomioka, Hideo; Chemistry Letters; (1984); p. 33 - 36 View in Reaxys With hydrogen selenide, triethylamine in methanol, Time= 3h, T= -30 °C , Yield given Asinger, Friedrich; Schmitz, Maria Karoline; Monatshefte fuer Chemie; vol. 113; (1982); p. 1191 - 1212 View in Reaxys Reaction Steps: 2 1.1: sulfuric acid / water / 120 h / 20 °C 1.2: 24 h / 20 °C 2.1: methanol; potassium chloride; sodium chloride; calcium chloride; sodium hydroxide; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid / water / pH 7.2 / Photolysis With methanol, sulfuric acid, potassium chloride, sodium chloride, calcium chloride, sodium hydroxide, magnesium chloride, N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid in water, 1.1: Pechmann condensation Fonseca, Andrea S.C.; Goncalves, M. Sameiro T.; Costa, Susana P.G.; Tetrahedron; vol. 68; nb. 38; (2012); p. 8024 - 8032 View in Reaxys

92 %Spectr. With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate in acetonitrile, Time= 24h, T= 20 °C , Irradiation Luo, Jian; Zhang, Xiang; Zhang, Jian; ACS Catalysis; vol. 5; nb. 4; (2015); p. 2250 - 2254 View in Reaxys O

Rx-ID: 2063304 View in Reaxys 44/824 Yield 98 %

Conditions & References General experimental procedure for deoximation to the corresponding carbonyl compounds

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General procedure: Oximes (1.0 mmol), Amberlyst-15 (0.02 g), FPA53-NO2(0.02 g), and solvent (1.5 mL) were introduced into a 25-cm-high, 90-mL autoclave with a glass tube inside equipped with magnetic stirrer (Scheme 2). Then the autoclave was charged with oxygen to 0.1 MPa. The reaction mixture was stirred at desirable temperature for special time. Progress of the reaction was monitored by thin-layer chromatography (TLC) or gas chromatography (GC). After the reaction, the resin (Amberlyst-15 and FPA53-NO2) was separated from the reaction mixture by filtration and extracted with 3 mL CH3CN (2 1.5 ml). The solvent was removed under reduced pressure. The residue was further purified by column chromatography on silica gel (300 mesh) with hexane/ethyl acetate to give the corresponding carbonyl compounds. With water, oxygen in acetonitrile, Time= 2h, T= 60 °C , p= 760.051Torr , Autoclave, Green chemistry Guo, Shu; Zeng, Renyou; Li, Caiye; Synthetic Communications; vol. 46; nb. 17; (2016); p. 1446 - 1453 View in Reaxys 95 %

With 2,6-dicarboxypyridinium fluorochromate, Time= 0.25h Tajbakhsh, Mahmood; Hosseinzadeh, Rahman; Ramzanian-Lahmali, Farhad; Sadatshahabi, Marzieh; Journal of the Chinese Chemical Society; vol. 52; nb. 5; (2005); p. 1005 - 1009 View in Reaxys

92 %

With 1,3,5-tribromo-hexahydro-<1,3,5>triazine-2,4,6-trione in acetonitrile, Time= 2.33h, T= 20 °C Habibi, Davood; Zolfigol, Mohammad Ali; Faraji, Ali Reza; Rahmani, Payam; Monatshefte fur Chemie; vol. 143; nb. 5; (2012); p. 809 - 814 View in Reaxys

91 %

With sodium perborate in acetic acid, Time= 1.5h, T= 90 - 95 °C Bandgar; Shaikh; Iyei, Suresh; Synthetic Communications; vol. 26; nb. 6; (1996); p. 1163 - 1168 View in Reaxys

91 %

With Montmorillonite K10, bis(trimethylsilyl)chromate, microwave irradiation Heravi, Majid M.; Ajami, Dariush; Tajbakhsh, Mahmood; Ghassemzadeh, Mitra; Monatshefte fur Chemie; vol. 131; nb. 10; (2000); p. 1109 - 1113 View in Reaxys

90 %

With formic acid, silica gel, Time= 0.0666667h, microwave irradiation Zhou, Jian-Feng; Tu, Shu-Jiang; Feng, Jun-Cai; Synthetic Communications; vol. 32; nb. 7; (2002); p. 959 - 962 View in Reaxys

89 %

With poly[N-(4-pyridinumdichromate)-p-styrenesulphonamide] in acetonitrile, Time= 3.5h, Heating Vaghei, Ramin Ghorbani; Khazaei, Ardeshir; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 1; (2004); p. 55 - 59 View in Reaxys

89 %

With phosphoric acid in water, Time= 4h, T= 95 °C Bhar, Sanjay; Guha, Sharmistha; Synthetic Communications; vol. 35; nb. 9; (2005); p. 1183 - 1188 View in Reaxys

89 %

With calcium hypochlorite, montmorillonite K-10 in chloroform, Time= 2h, T= 20 °C Movassagh, Barahman; Dahaghin, Ebrahim; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 45; nb. 6; (2006); p. 1541 - 1543 View in Reaxys

84 %

With alumina supported chromium(VI) oxide, Time= 0.0111111h, microwave irradiation, deoximination Heravi, Majid M.; Ajami, Dariush; Hekmatshoar, Rahim; Beheshtiha, Yahya Sh.; Assadollah, Karim; Ghassemzadeh, Mitra; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 55; nb. 5; (2000); p. 431 - 433 View in Reaxys

84 %

With alumina supported chromium(VI) oxide in dichloromethane, Time= 0.666667h

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Heravi, Majid M.; Ajami, Darush; Shoar, Rahim Hekmat; Sarmad, Nooshin; Faridbod, Farnoush; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 12; (2004); p. 2423 - 2427 View in Reaxys 82 %

With manganese(IV) oxide, potassium permanganate, Time= 0.5h, T= 20 °C Shaabani, Ahmad; Naderi, Soheila; Rahmati, Abbas; Badri, Zahra; Darvishi, Maria; Lee, Donald G.; Synthesis; nb. 18; (2005); p. 3023 - 3025; Art.No: P07005SS View in Reaxys

82 %

With oxygen, sodium nitrite in dichloromethane, water, Time= 9h, T= 25 °C , p= 760.051Torr , Sealed system Zhang, Guofu; Wen, Xin; Wang, Yong; Mo, Weimin; Ding, Chengrong; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4665 - 4668 View in Reaxys

80 %

With ammonium chlorochromate, montmorillonite K-10, Time= 0.1h, microwave irradiation, deoximation Heravi, Majid M.; Beheshtiha, Yahya S.; Ghasemzadeh, Mitra; Hekmatshoar, Rahim; Sarmad, Nooshin; Monatshefte fur Chemie; vol. 131; nb. 2; (2000); p. 187 - 190 View in Reaxys

80 %

With sodium bromate, ion exchange resin, Time= 0.25h, T= 25 - 30 °C , ultrasonic irradiation Shaabani, Ahmad; Rahmati, Abbas; Naderi, Soheila; Synthetic Communications; vol. 37; nb. 22; (2007); p. 4035 - 4042 View in Reaxys

78 %

With dinitrogen tetraoxide in tetrahydrofuran, Time= 0.166667h, T= -40 °C Shim, Sung Bo; Kim, Kweon; Kim, Yong Hae; Tetrahedron Letters; vol. 28; nb. 6; (1987); p. 645 - 648 View in Reaxys

77 %

With bismuth(lll) trifluoromethanesulfonate, bismuth(III) bromide in water, acetone, acetonitrile, Time= 2h, Heating Arnold, Joshua N.; Hayes, Patrick D.; Kohaus, Robert L.; Mohan, Ram S.; Tetrahedron Letters; vol. 44; nb. 51; (2003); p. 9173 - 9176 View in Reaxys

100 %Chro- With oxygen in acetonitrile, Time= 4h, T= 20 - 32 °C , p= 760.051Torr , Irradiation mat. Abedi, Sedigheh; Karimi, Babak; Kazemi, Foad; Bostina, Mihnea; Vali, Hojatollah; Organic and Biomolecular Chemistry; vol. 11; nb. 3; (2013); p. 416 - 419 View in Reaxys 100 %Chro- With oxygen in acetonitrile, Time= 24h, p= 760.051Torr , Irradiation mat. Abedi, Sedigheh; Morsali, Ali; New Journal of Chemistry; vol. 39; nb. 2; (2015); p. 931 - 937 View in Reaxys O HO

Rx-ID: 28530071 View in Reaxys 45/824 Yield

Conditions & References With tert.-butylhydroperoxide, [(pymox-Me2)2RuCl2]+BF4- in water, T= 20 °C Yi, Chae S.; Kwon, Ki-Hyeok; Lee, Do W.; Organic Letters; vol. 11; nb. 7; (2009); p. 1567 - 1569 View in Reaxys

6 %Chromat., 94 %Chromat.

2.1.4. General procedure for the oxidation of ethyl benzenes General procedure: A mixture containing substrate (0.5 mmol), t-butyl hydroperox-ide (TBHP) (1 mmol) and Au/rGO (15 mg) was mixed in acetonitrile(5 mL). The resulting mixture was stirred at 70C for 24 h. Progressof the reaction was monitored by TLC (silica gel; n-hexane/ethylacetate). After desired time, the crude material was extracted withethyl acetate and the extract

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concentrated under reduced pressure.The obtained material was analyzed by gas chromatography usingdodecane as internal standard. With tert.-butylhydroperoxide in acetonitrile, Time= 24h, T= 70 °C , Catalytic behavior, Reagent/catalyst Pocklanova, Radka; Gawande, Manoj B.; Rathi, Anuj K.; Datta, Kasibhatta Kumara Ramanatha; Ranc, Vaclav; Cepe, Klara; Petr, Martin; Varma, Rajender S.; Kvitek, Libor; Zboril, Radek; Journal of Molecular Catalysis A: Chemical; vol. 424; (2016); p. 121 - 127 View in Reaxys O NH 2

H 2N

Rx-ID: 28538751 View in Reaxys 46/824 Yield 49 %Chromat.

Conditions & References With transaminase ATA-114, pyridoxal 5'-phosphate, sodium pyruvate, Time= 24h, T= 30 °C , pH= 7.0, aq. phosphate buffer, Resolution of racemate, Enzymatic reaction, optical yield given as percent ee Koszelewski, Dominik; Clay, Dorina; Rozzell, David; Kroutil, Wolfgang; European Journal of Organic Chemistry; nb. 14; (2009); p. 2289 - 2292 View in Reaxys

72 %Chromat.

Stage 1: With transaminase ATA-114, pyridoxal 5'-phosphate, sodium pyruvate, Time= 24h, T= 30 °C , pH= 7.0, aq. phosphate buffer, Resolution of racemate, Enzymatic reaction Stage 2: With D-Alanine, transaminase ATA-117, Time= 24h, T= 30 °C , aq. phosphate buffer, Enzymatic reaction, optical yield given as percent ee Koszelewski, Dominik; Clay, Dorina; Rozzell, David; Kroutil, Wolfgang; European Journal of Organic Chemistry; nb. 14; (2009); p. 2289 - 2292 View in Reaxys With L-amino acid oxidase, ATA-113, pyridoxal 5'-phosphate, 2-oxo-propionic acid, Time= 3h, T= 30 °C , pH= 8, Resolution of racemate, aq. phosphate buffer, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Truppo, Matthew D.; Turner, Nicholas J.; Rozzell, J. David; Chemical Communications; nb. 16; (2009); p. 2127 - 2129 View in Reaxys With water in dimethyl sulfoxide, Time= 18h, T= 30 °C , pH= 7, aq. phosphate buffer, Microbiological reaction, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Leisch, Hannes; Grosse, Stephan; Iwaki, Hiroaki; Hasegawa, Yoshie; Lau, Peter C.K.; Canadian Journal of Chemistry; vol. 90; nb. 1; (2012); p. 39 - 45 View in Reaxys Determination of activity in kinetic resolution mode. General procedure: The activity measurements were performed in a TECAN Infinite 200 PRO reader, and all measurements were performed at least in triplicate. A direct photometric assay was used28, in which the enzymatic reaction took place in CHES buffer (50 mM, pH 9.0) at 30 °C in a total volume of 200 μl. 1 mM racemic amine (1a–4a) and 2 mM pyruvate were added to the buffer (final concentrations) containing the TA of interest. Due to the preparation of the amine stock solution in organic solvent, 5percent (vol/vol) 2-propanol or dimethylsulfoxide (DMSO, 0.1percent for compounds 5–7) was present in the final reaction medium. The kinetic resolution was initiated by the addition of the amine acceptor (pyruvate). The final concentration of the enzyme varied between 2 and 800 μg ml−1, depending on the specific activity towards the substrates under examination. The production of the corresponding ketones (1b–7b) was monitored at the optimum wavelength for each compound (1b, 16,562M−1 cm−1 at 264 nm; 2b, 9,646 M−1 cm−1at 245 nm; 3b, 5,714 M−1 cm−1 at 340 nm; 4b, 6,115 M−1 cm−1 at 245 nm (ref. 27);5b and 6b, 6,530 M−1 cm−1 at 242 nm (ref. 15); and 7b, 7,098 M−1 cm−1at 252 nm (ref. 14)). With pyridoxal 5'-phosphate, fold class I transaminase from Ruegeria sp. TM1040(Y59W/Y87F/Y152F/T231A), piruvate in dimethyl sulfoxide, T= 30 °C , pH= 9, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Pavlidis, Ioannis V.; Weiß, Martin S.; Genz, Maika; Spurr, Paul; Hanlon, Steven P.; Wirz, Beat; Iding, Hans; Bornscheuer, Uwe T.; Nature Chemistry; vol. 8; nb. 11; (2016); p. 1076 - 1082

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View in Reaxys O O

Rx-ID: 29600986 View in Reaxys 47/824 Yield

Conditions & References With toluene-4-sulfonic acid, benzyl alcohol, Heating Sonawane, Manoj R.; Cisaova, Ivana; Lyapkalo, Ilya M.; Chemical Communications; vol. 46; nb. 15; (2010); p. 2656 - 2658 View in Reaxys With trifluorormethanesulfonic acid, trimethyl orthoformate in chloroform-d1 Malmedy, Florence; Wirth, Thomas; Chemistry - A European Journal; vol. 22; nb. 45; (2016); p. 16072 - 16077 View in Reaxys O

Rx-ID: 40744690 View in Reaxys 48/824 Yield

Conditions & References With oxygen, Time= 0.25h, T= 120 °C , Sonication Santiago-Portillo, Andrea; Navalón, Sergio; Cirujano, Francisco G.; Xamena, Francesc X. Llabrés I; Alvaro, Mercedes; Garcia, Hermenegildo; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3216 - 3224 View in Reaxys With [(copper(II))0.5(lanthanum(III))2(monoacid 3,5-pyridinedicarboxylate)(3,5-pyridinedicarboxylate)2(sulfate)(H2O)2] monohydrate, oxygen in neat (no solvent), T= 120 °C , p= 760.051Torr Cancino; Vega; Santiago-Portillo, Andrea; Navalon, Sergio; Alvaro, Mercedes; Aguirre; Spodine; García, Hermenegildo; Catalysis Science and Technology; vol. 6; nb. 11; (2016); p. 3727 - 3736 View in Reaxys

Rx-ID: 42519710 View in Reaxys 49/824 Yield

Conditions & References Peroxidation of n-propylbenzene under air saturated conditions In a 50 mL, two-neck round bottom flask, catalyst (100 mg) and cumene hydroperoxide (140 mmol) were added to 10 mL of npropylbenzene and the reaction was heated to 40 or 80 °C. An aliquot was taken from thereaction mixture every hour, centrifuged and subsequently analyzed by HPLC. Control reactions were carried out using the support itself and in the absence of catalyst. With Cumene hydroperoxide, T= 40 °C , Temperature Crites, Charles-Oneil L.; Netto-Ferreira, José Carlos; Hallett-Tapley, Geniece L.; Scaiano, Juan Cesar; Journal of the Brazilian Chemical Society; vol. 27; nb. 2; (2016); p. 334 - 340

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View in Reaxys O O

HO HO

OH O

Rx-ID: 42690700 View in Reaxys 50/824 Yield

Conditions & References With copper-doped magnesium-aluminum mixed porous metal oxide, T= 310 °C , High pressure, Autoclave, Sealed tube, Mechanism Bernt, Christopher M.; Bottari, Giovanni; Barrett, Jacob A.; Scott, Susannah L.; Barta, Katalin; Ford, Peter C.; Catalysis Science and Technology; vol. 6; nb. 9; (2016); p. 2984 - 2994 View in Reaxys O

Rx-ID: 43000250 View in Reaxys 51/824 Yield

Conditions & References Catalyzed epoxidation of olefin General procedure: Compound 1 (0.01 mmol, 5.0 mg), olefin (1 mmol), TBHP (tertbutylhydroperoxide, 2 mmol), acetonitrile (2 mL) were added to a glass tube, then the catalytic reaction was performed on a Wattecs Parallel Reactor at 75 °C for 24 h. After the reaction was completed, the resulting mixture was analyzed by GC–MS and GC. With tert.-butylhydroperoxide, [Zn(1-ethylimidazole)3]2V4O12 in acetonitrile, Time= 24h Niu, Yan-Hong; Yang, Song; Li, Ji-Kun; Xu, Yan-Qing; Hu, Chang-Wen; Chinese Chemical Letters; vol. 27; nb. 5; (2016); p. 649 - 654 View in Reaxys

O O

Rx-ID: 1752600 View in Reaxys 52/824 Yield 92 %

Conditions & References With tetrachlorosilane in dichloromethane, Time= 0.333333h, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Hazarkhani, Hassan; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 177; nb. 12; (2002); p. 2847 - 2858

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View in Reaxys 84 %

With sodium tetrahydroborate, nickel(II) chloride hexahydrate in methanol, Time= 5h, Reflux, chemoselective reaction Khurana, Jitender M.; Dawra, Kiran; Sharma, Purnima; RSC Advances; vol. 5; nb. 16; (2015); p. 12048 - 12051 View in Reaxys With tellurium, sodium tetrahydroborate, water, 1.) EtOH, 25 deg C, 30 min, Yield given. Multistep reaction Lue, Ping; Fan, Wei-Qiang; Zhou, Xun-Jun; Synthesis; nb. 9; (1989); p. 692 - 693 View in Reaxys O

Rx-ID: 2032312 View in Reaxys 53/824 Yield

Conditions & References

88 %

With water in 1,4-dioxane, Time= 5h, Heating Kulinkovich, O.G.; Sviridov, S.V.; Vasilevskii, D.A.; Savchenko, A.I.; Pritytskaya, T.S.; Journal of Organic Chemistry USSR (English Translation); vol. 27; nb. 2; (1991); p. 250 - 253; Zhurnal Organicheskoi Khimii; vol. 27; nb. 2; (1991); p. 294 298 View in Reaxys

80 %

With copper diacetate, Time= 8h, Reflux, Reagent/catalyst Shen, Mei-Hua; Lu, Xiao-Long; Xu, Hua-Dong; RSC Advances; vol. 5; nb. 120; (2015); p. 98757 - 98761 View in Reaxys

70 %

Time= 12.5h, T= 220 - 225 °C Barluenga, Jose; Florez, Josefa; Yus, Miguel; Synthesis; nb. 8; (1983); p. 647 - 649 View in Reaxys O Cl

Rx-ID: 9600579 View in Reaxys 54/824 Yield 93 %

Conditions & References With 1-dodecyl-3-methylimidazolium iron chloride, periodic acid, Time= 2h, T= 30 °C Hu, Yu Lin; Liu, Qi Fa; Lu, Ting Ting; Lu, Ming; Catalysis Communications; vol. 11; nb. 10; (2010); p. 923 - 927 View in Reaxys

89 %

With dihydrogen peroxide in ethanol, Time= 6h, Reflux, Green chemistry Bayat, Ahmad; Shakourian-Fard, Mehdi; Ramezanpour, Shaghayegh; Mahmoodi Hashemi, Mohammad; New Journal of Chemistry; vol. 39; nb. 5; (2015); p. 3845 - 3851 View in Reaxys

72 %

With dihydrogen peroxide, vanadia, Aliquat 336 in water, Time= 10h, Heating Li, Chunbao; Zheng, Pengwu; Li, Jie; Zhang, Hang; Cui, Yi; Shao, Qiyun; Ji, Xiujie; Zhang, Jian; Zhao, Pengying; Xu, Yanli; Angewandte Chemie - International Edition; vol. 42; nb. 41; (2003); p. 5063 - 5066 View in Reaxys

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NH 2

Rx-ID: 37344855 View in Reaxys 55/824 Yield

Conditions & References With Paracoccus denitrificans η-transaminase, piruvate in aq. phosphate buffer, T= 37 °C , pH= 7, Enzymatic reaction, Reagent/ catalyst Park, Eul-Soo; Park, Sae-Rom; Han, Sang-Woo; Dong, Joo-Young; Shin, Jong-Shik; Advanced Synthesis and Catalysis; vol. 356; nb. 1; (2014); p. 212 - 220 View in Reaxys With 2-oxo-propionic acid in aq. phosphate buffer, T= 37 °C , pH= 7, Enzymatic reaction, Kinetics, Reagent/catalyst Han, Sang-Woo; Park, Eul-Soo; Dong, Joo-Young; Shin, Jong-Shik; Advanced Synthesis and Catalysis; vol. 357; nb. 12; (2015); p. 2712 - 2720 View in Reaxys

O O

Rx-ID: 39423790 View in Reaxys 56/824 Yield

Conditions & References

18 %Chromat., 81 %Chromat.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, copper(II) bis(trifluoromethanesulfonate), caesium carbonate, (2,6-bis[(4S)-(-)-isopropyl-2-oxazolin-2-yl]pyridine), potassium iodide in toluene, Time= 24h, T= 100 °C , Inert atmosphere Xu, Tao; Hu, Xile; Angewandte Chemie - International Edition; vol. 54; nb. 4; (2015); p. 1307 - 1311; Angew. Chem.; vol. 127; nb. 4; (2015); p. 1323 - 1327,5 View in Reaxys O

NH O

Rx-ID: 39863399 View in Reaxys 57/824 Yield

Conditions & References Reaction Steps: 2 1.1: hydrogenchloride / water / 1 h / Reflux 1.2: pH 10 2.1: 4-tert-butyl-5-methoxy-1,2-benzoquinone; oxygen / acetonitrile / 48 h / 60 °C / Schlenk technique With hydrogenchloride, 4-tert-butyl-5-methoxy-1,2-benzoquinone, oxygen in water, acetonitrile Qin, Yan; Zhang, Long; Lv, Jian; Luo, Sanzhong; Cheng, Jin-Pei; Organic Letters; vol. 17; nb. 6; (2015); p. 1469 - 1472 View in Reaxys

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O HO

Rx-ID: 39986863 View in Reaxys 58/824 Yield

Conditions & References Reaction Steps: 2 1: N,N-dimethyl acetamide / 24 h / 120 °C 2: hydrogen; 5% Rh/C / ethanol / 12 h / 20 °C With 5% Rh/C, hydrogen in ethanol, N,N-dimethyl acetamide Borah, Ashwini; Goswami, Limi; Neog, Kashmiri; Gogoi, Pranjal; Journal of Organic Chemistry; vol. 80; nb. 9; (2015); p. 4722 - 4728 View in Reaxys O

O HO

Rx-ID: 39986874 View in Reaxys 59/824 Yield

Conditions & References With 5% Rh/C, hydrogen in ethanol, Time= 12h, T= 20 °C , Reagent/catalyst Borah, Ashwini; Goswami, Limi; Neog, Kashmiri; Gogoi, Pranjal; Journal of Organic Chemistry; vol. 80; nb. 9; (2015); p. 4722 - 4728 View in Reaxys O HO

Rx-ID: 40107377 View in Reaxys 60/824 Yield

Conditions & References With [Ru(η3:η3-C10H16)Cl2]2 in water, Time= 1h, T= 75 °C Vázquez-Romero, Ana; Gómez, Antonio Bermejo; Martín-Matute, Belén; ACS Catalysis; vol. 5; nb. 2; (2015); p. 708 - 714 View in Reaxys O

Mg Br

Rx-ID: 40116702 View in Reaxys 61/824 Yield 75 %

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dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the desired amine 6. Stage 1: With 2,6-di-tert-butyl-4-methylpyridine, trifluoromethylsulfonic anhydride in dichloromethane, Time= 2h, T= -78 - 0 °C , Inert atmosphere Stage 2: in diethyl ether, dichloromethane, Time= 2h, T= -78 °C , Inert atmosphere, chemoselective reaction Huang, Pei-Qiang; Wang, Yu; Xiao, Kai-Jiong; Huang, Ying-Hong; Tetrahedron; vol. 71; nb. 24; (2015); p. 4248 - 4254; Art.No: 26677 View in Reaxys O

N Mg Br

Rx-ID: 40116706 View in Reaxys 62/824 Yield 51 %

Conditions & References 7 : 4.2. General procedure for the direct transformation of tertiary amides into ketones and amines General procedure: Tf2O (1.2 equiv) was added dropwise to a cooled (−78 °C) solution of amide 5 (1.0 equiv) and DTBMP (1.2 equiv) in CH2Cl2 (5 mL). The reaction was allowed warming to 0 °C over 2 h. A solution of Grignard reagent (1.0 equiv) in Et2O was added dropwise to the resultant mixture at −78 °C, and the mixture was stirred at the same temperature for 2 h. The reaction mixture was then quenched with an aqueous solution of 15percent HCl (5 mL). The organic layer was separated and the aqueous phase was extracted with diethyl ether (3×5 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the desired ketone 1. To isolate the corresponding amine, the aqueous solution layer was basified with an aqueous solution of 15percent NaOH (6 mL), and extracted with dichloromethane (3×10 mL), the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the desired amine 6. Stage 1: With 2,6-di-tert-butyl-4-methylpyridine, trifluoromethylsulfonic anhydride in dichloromethane, Time= 2h, T= -78 - 0 °C , Inert atmosphere Stage 2: in diethyl ether, dichloromethane, Time= 2h, T= -78 °C , Inert atmosphere, chemoselective reaction Huang, Pei-Qiang; Wang, Yu; Xiao, Kai-Jiong; Huang, Ying-Hong; Tetrahedron; vol. 71; nb. 24; (2015); p. 4248 - 4254; Art.No: 26677 View in Reaxys O

Rx-ID: 40177683 View in Reaxys 63/824 Yield 96 %

Conditions & References With tert.-butylhydroperoxide, palladium diacetate, toluene-4-sulfonic acid in water, acetonitrile, Time= 6h, T= 20 °C , Wacker Oxidation, Catalytic behavior, Solvent, Reagent/catalyst, chemoselective reaction Zhao, Jinwu; Liu, Li; Xiang, Shijian; Liu, Qiang; Chen, Huoji; Organic and Biomolecular Chemistry; vol. 13; nb. 20; (2015); p. 5613 - 5616 View in Reaxys Reaction Steps: 2 1: palladium diacetate; tert.-butylhydroperoxide; toluene-4-sulfonic acid / water; acetonitrile / 3 h / 20 °C 2: palladium diacetate; tert.-butylhydroperoxide; toluene-4-sulfonic acid / water; acetonitrile / 6 h / 20 °C With tert.-butylhydroperoxide, palladium diacetate, toluene-4-sulfonic acid in water, acetonitrile, 1: |Wacker Oxidation / 2: | Wacker Oxidation Zhao, Jinwu; Liu, Li; Xiang, Shijian; Liu, Qiang; Chen, Huoji; Organic and Biomolecular Chemistry; vol. 13; nb. 20; (2015); p. 5613 - 5616

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View in Reaxys O O

Rx-ID: 40177684 View in Reaxys 64/824 Yield

Conditions & References With tert.-butylhydroperoxide, palladium diacetate, acetic acid in water, acetonitrile, Time= 6h, T= 20 °C , Wacker Oxidation, Catalytic behavior, Solvent, Overall yield = 25 percentSpectr.; chemoselective reaction Zhao, Jinwu; Liu, Li; Xiang, Shijian; Liu, Qiang; Chen, Huoji; Organic and Biomolecular Chemistry; vol. 13; nb. 20; (2015); p. 5613 - 5616 View in Reaxys With tert.-butylhydroperoxide, palladium diacetate in water, acetonitrile, Time= 6h, T= 20 °C , Wacker Oxidation, Catalytic behavior, Solvent, Reagent/catalyst, Overall yield = 36 percentSpectr.; chemoselective reaction Zhao, Jinwu; Liu, Li; Xiang, Shijian; Liu, Qiang; Chen, Huoji; Organic and Biomolecular Chemistry; vol. 13; nb. 20; (2015); p. 5613 - 5616 View in Reaxys O

Rx-ID: 40177686 View in Reaxys 65/824 Yield 13 %, 68 %

Conditions & References With tert.-butylhydroperoxide, palladium diacetate, toluene-4-sulfonic acid in water, acetonitrile, Time= 3h, T= 20 °C , Wacker Oxidation, chemoselective reaction Zhao, Jinwu; Liu, Li; Xiang, Shijian; Liu, Qiang; Chen, Huoji; Organic and Biomolecular Chemistry; vol. 13; nb. 20; (2015); p. 5613 - 5616 View in Reaxys O

Rx-ID: 40177688 View in Reaxys 66/824 Yield 98 %

Conditions & References With tert.-butylhydroperoxide, palladium diacetate, toluene-4-sulfonic acid in water, acetonitrile, Time= 6h, T= 20 °C , Wacker Oxidation, chemoselective reaction Zhao, Jinwu; Liu, Li; Xiang, Shijian; Liu, Qiang; Chen, Huoji; Organic and Biomolecular Chemistry; vol. 13; nb. 20; (2015); p. 5613 - 5616 View in Reaxys O

Rx-ID: 40289704 View in Reaxys 67/824

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Yield

Conditions & References

53 %, 18 %, With iron(III) trifluoromethanesulfonate, C65H77N5O4S2, oxygen in 1,2-dichloro-ethane, Time= 8h, T= 75 °C , p= 760.051Torr , 7% Inert atmosphere Gonzalez-De-Castro, Angela; Xiao, Jianliang; Journal of the American Chemical Society; vol. 137; nb. 25; (2015); p. 8206 8218 View in Reaxys

N H

O H 2N Cl

Rx-ID: 40804013 View in Reaxys 68/824 Yield 88 %

Conditions & References General procedure for N-deacylation of secondary amides General procedure: Tf2O (185μL, 1.1mmol) was added dropwise to a cooled (0°C) solution of amide (1.0mmol) and 2-fluoropyridine (103μL, 1.2mmol) in dichloromethane (4mL). After stirring at 0°C for 30min, the mixture was cannulated to a freshly prepared organocerium reagent/complex (3.0mmol) in THF (15mL) at −78°C and stirred for 2h. Aqueous HCl solution (3mol/L, 5mL) was added to quench the reaction and the mixture was allowed to warm to r.t. and stirred for 2h. Ammonium hydroxide solution (25percent, 5mL) was then added to the mixture. The organic layer was separated and the aqueous phase was extracted with diethyl ether (3× 10mL). The combined organic layers were washed with brine (3× 3mL) and concentrated under reduced pressure to about 1/3 volume. The residual organic phase was then extracted with aqueous HCl solution (3mol/L, 3× 5mL). The separated organic phase was washed with brine (5mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to afford ketone. The aqueous phases were combined, washed with diethyl ether (5mL), basified with an ammonium hydroxide solution (25percent, 5mL) and back-extracted with diethyl ether (5× 20mL). The ether layers were combined, washed with brine (5mL), dried over anhydrous MgSO4, filtered, acidified with a solution of HCl in ethyl acetate (3mol/L, 5mL) and concentrated under reduced pressure to afford the desired amine hydrochloride salt. Stage 1: With 2-fluoropyridine, trifluoromethylsulfonic anhydride in dichloromethane, Time= 0.5h, T= 0 °C Stage 2: With cerium(III) chloride in tetrahydrofuran, dichloromethane, Time= 2h, T= -78 °C Stage 3: With hydrogenchloride in ethyl acetate Wang, Ai-E.; Chang, Zong; Liu, Yong-Peng; Huang, Pei-Qiang; Chinese Chemical Letters; vol. 26; nb. 9; (2015); p. 1055 1058 View in Reaxys

O O

N H

Mg Br

H 2N

Rx-ID: 40804017 View in Reaxys 69/824 Yield 76 %

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with diethyl ether (3× 10mL). The combined organic layers were washed with brine (3× 3mL) and concentrated under reduced pressure to about 1/3 volume. The residual organic phase was then extracted with aqueous HCl solution (3mol/L, 3× 5mL). The separated organic phase was washed with brine (5mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to afford ketone. The aqueous phases were combined, washed with diethyl ether (5mL), basified with an ammonium hydroxide solution (25percent, 5mL) and back-extracted with diethyl ether (5× 20mL). The ether layers were combined, washed with brine (5mL), dried over anhydrous MgSO4, filtered, acidified with a solution of HCl in ethyl acetate (3mol/L, 5mL) and concentrated under reduced pressure to afford the desired amine hydrochloride salt. Stage 1: With 2-fluoropyridine, trifluoromethylsulfonic anhydride in dichloromethane, Time= 0.5h, T= 0 °C Stage 2: With cerium(III) chloride in tetrahydrofuran, dichloromethane, Time= 2h, T= -78 °C Stage 3: With hydrogenchloride in ethyl acetate Wang, Ai-E.; Chang, Zong; Liu, Yong-Peng; Huang, Pei-Qiang; Chinese Chemical Letters; vol. 26; nb. 9; (2015); p. 1055 1058 View in Reaxys O

N H

Mg Br

H 2N

Rx-ID: 40804019 View in Reaxys 70/824 Yield 63 %

H 2N

Rx-ID: 40804020 View in Reaxys 71/824 Yield 87 %

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solution (25percent, 5mL) was then added to the mixture. The organic layer was separated and the aqueous phase was extracted with diethyl ether (3× 10mL). The combined organic layers were washed with brine (3× 3mL) and concentrated under reduced pressure to about 1/3 volume. The residual organic phase was then extracted with aqueous HCl solution (3mol/L, 3× 5mL). The separated organic phase was washed with brine (5mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to afford ketone. The aqueous phases were combined, washed with diethyl ether (5mL), basified with an ammonium hydroxide solution (25percent, 5mL) and back-extracted with diethyl ether (5× 20mL). The ether layers were combined, washed with brine (5mL), dried over anhydrous MgSO4, filtered, acidified with a solution of HCl in ethyl acetate (3mol/L, 5mL) and concentrated under reduced pressure to afford the desired amine hydrochloride salt. Stage 1: With 2-fluoropyridine, trifluoromethylsulfonic anhydride in dichloromethane, Time= 0.5h, T= 0 °C Stage 2: With cerium(III) chloride in tetrahydrofuran, dichloromethane, Time= 2h, T= -78 °C Stage 3: With hydrogenchloride in ethyl acetate Wang, Ai-E.; Chang, Zong; Liu, Yong-Peng; Huang, Pei-Qiang; Chinese Chemical Letters; vol. 26; nb. 9; (2015); p. 1055 1058 View in Reaxys O

N H

NH 2

Rx-ID: 40804021 View in Reaxys 72/824 Yield 70 %

O O

Mg Br

NH 2

Rx-ID: 40804022 View in Reaxys 73/824 Yield 77 %

Conditions & References General procedure for N-deacylation of secondary amides

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General procedure: Tf2O (185μL, 1.1mmol) was added dropwise to a cooled (0°C) solution of amide (1.0mmol) and 2-fluoropyridine (103μL, 1.2mmol) in dichloromethane (4mL). After stirring at 0°C for 30min, the mixture was cannulated to a freshly prepared organocerium reagent/complex (3.0mmol) in THF (15mL) at −78°C and stirred for 2h. Aqueous HCl solution (3mol/L, 5mL) was added to quench the reaction and the mixture was allowed to warm to r.t. and stirred for 2h. Ammonium hydroxide solution (25percent, 5mL) was then added to the mixture. The organic layer was separated and the aqueous phase was extracted with diethyl ether (3× 10mL). The combined organic layers were washed with brine (3× 3mL) and concentrated under reduced pressure to about 1/3 volume. The residual organic phase was then extracted with aqueous HCl solution (3mol/L, 3× 5mL). The separated organic phase was washed with brine (5mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to afford ketone. The aqueous phases were combined, washed with diethyl ether (5mL), basified with an ammonium hydroxide solution (25percent, 5mL) and back-extracted with diethyl ether (5× 20mL). The ether layers were combined, washed with brine (5mL), dried over anhydrous MgSO4, filtered, acidified with a solution of HCl in ethyl acetate (3mol/L, 5mL) and concentrated under reduced pressure to afford the desired amine hydrochloride salt. Stage 1: With 2-fluoropyridine, trifluoromethylsulfonic anhydride in dichloromethane, Time= 0.5h, T= 0 °C Stage 2: With cerium(III) chloride in tetrahydrofuran, dichloromethane, Time= 2h, T= -78 °C Stage 3: With hydrogenchloride in ethyl acetate Wang, Ai-E.; Chang, Zong; Liu, Yong-Peng; Huang, Pei-Qiang; Chinese Chemical Letters; vol. 26; nb. 9; (2015); p. 1055 1058 View in Reaxys O NH 2 H

Rx-ID: 40846846 View in Reaxys 74/824 Yield

Conditions & References With 2-oxo-propionic acid in aq. phosphate buffer, T= 37 °C , pH= 7, Enzymatic reaction, Kinetics, Reagent/catalyst Han, Sang-Woo; Park, Eul-Soo; Dong, Joo-Young; Shin, Jong-Shik; Advanced Synthesis and Catalysis; vol. 357; nb. 12; (2015); p. 2712 - 2720 View in Reaxys

O O

Br Br

O O

Rx-ID: 40928945 View in Reaxys 75/824 Yield

Conditions & References 2.3.5.2. Rearrangement of 2-bromopropiophenone ethylene acetal. With PdCl2: a solution of 2-bromopropiophenone ethyleneacetal (75.76 mg, 0.2947 mmol, 1 equiv.) in 1,2-dichlorobenzene(3.29 mL) was poured onto catalyst (mass corresponding to0.01238 mmol of Pd, 0.04 equiv.), with water (5.31 L, 0.2947 mmol1 equiv.). The resulting suspension was stirred at 180C for 20 h.The mixture reaction was analyzed by GC–MS as described above. With palladium dichloride in water, 1,2-dichloro-benzene, Time= 20h, T= 180 °C Garel, Claire; Renard, Brice-Loc; Escande, Vincent; Galtayries, Anouk; Hesemann, Peter; Grison, Claude; Applied Catalysis A: General; vol. 504; (2015); p. 272 - 286 View in Reaxys

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O HO O

B N

Rx-ID: 41237243 View in Reaxys 76/824 Yield

Conditions & References

95 %

With trifluorormethanesulfonic acid, water, palladium diacetate, 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine, Time= 5h, T= 60 °C Yousuf, Md; Das, Tuluma; Adhikari, Susanta; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8763 - 8770 View in Reaxys

O O

HO O

S NH

Rx-ID: 41503804 View in Reaxys 77/824 Yield

Conditions & References With copper diacetate in toluene, Time= 12h, Reflux, Reagent/catalyst, Solvent Shen, Mei-Hua; Lu, Xiao-Long; Xu, Hua-Dong; RSC Advances; vol. 5; nb. 120; (2015); p. 98757 - 98761 View in Reaxys O

Rx-ID: 2064377 View in Reaxys 78/824 Yield 78 %

Conditions & References 2.1 Biotransformations with D. carota roots General procedure: Edible carrot (D. carota) roots were purchased in a local market in Montevideo, Uruguay. The roots were thoroughly washed with running tap water and the external layer was removed with a sterile knife. Then, the plant tissue was washed with sterile distilled water, disinfected with 10percent sodium hypochlorite solution for 3min, and rinsed with sterile distilled water. Next, the plant parts were soaked in 70percent aq. ethanol for 3min and rinsed three times with sterile distilled water. Disinfected plant tissues were sliced with a sterile knife. Immediately, 90g of plant fragments were transferred to a 250mL sterile Erlenmeyer flask and suspended in 100mL of sterile water containing 90mg of the appropriate substrate. The culture was incubated at 28°C and 150rpm in a ZHICHENG ZHWY-211B orbital shaker for 48h. With Carrot (Daucus carota), Time= 48h, T= 28 °C , Microbiological reaction, Enzymatic reaction, Reagent/catalyst Coronel, Camila; Arce, Gabriel; Iglesias, Cesar; Noguera, Cynthia Magallanes; Bonnecarrere, Paula Rodriguez; Giordano, Sonia Rodriguez; Gonzalez, David; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 94 - 98 View in Reaxys in N,N,N,N,N,N-hexamethylphosphoric triamide, Ambient temperature, Irradiation, Rate constant, Mechanism Kimura, Norio; Takamuku, Setsuo; Bulletin of the Chemical Society of Japan; vol. 64; nb. 8; (1991); p. 2433 - 2437 View in Reaxys Reaction Steps: 2 1: azide(1-) / N,N-dimethyl-formamide 2: Carrot (Daucus carota) / 48 h / 28 °C / Microbiological reaction; Enzymatic reaction With azide(1-) in N,N-dimethyl-formamide

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Coronel, Camila; Arce, Gabriel; Iglesias, Cesar; Noguera, Cynthia Magallanes; Bonnecarrere, Paula Rodriguez; Giordano, Sonia Rodriguez; Gonzalez, David; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 94 - 98 View in Reaxys 36 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Rhodotorula glutinis KCh 242 in acetone, Time= 6h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

Rx-ID: 2064378 View in Reaxys 79/824 Yield 58 %, 30 %

Conditions & References in ethanol, Time= 16h, T= 20 °C , bakers' yeast in aq. glucose solution Fronza; Fuganti; Grasselli; Mele; Journal of Organic Chemistry; vol. 56; nb. 21; (1991); p. 6019 - 6023 View in Reaxys 2.2.1. General procedure for biotransformations with yeast strains General procedure: Fresh plates of each yeast strain were streaked from the frozen stock in PDA. A single colony was used to inoculate 100mL of YM Broth. The culture was incubated at 28°C and 150rpm for 48h and the cells were collected by centrifugation at 4000rpm and 4°C for 15min. The pellet was washed three times with 50mL physiological serum. Afterward, 2g of yeast cells (wet weight) were suspended in 20mL of 10percent dextrose solution and 30mg of the appropriate substrate were added. The culture was incubated at 28°C and 150rpm in an orbital shaker ZHICHENG ZHWY-211B for 48h. With yeast strain Pichia sp. CR, Time= 48h, T= 28 °C , Microbiological reaction, Enzymatic reaction Coronel, Camila; Arce, Gabriel; Iglesias, Cesar; Noguera, Cynthia Magallanes; Bonnecarrere, Paula Rodriguez; Giordano, Sonia Rodriguez; Gonzalez, David; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 94 - 98 View in Reaxys O O

Rx-ID: 8868700 View in Reaxys 80/824 Yield 46 %, 45 %

Conditions & References With tetrafluoroboric acid, oxygen, palladium diacetate, p-benzoquinone in N,N-dimethyl acetamide, water, acetonitrile, Time= 16h, T= 20 °C , Overall yield = 91 percent; regioselective reaction Morandi, Bill; Wickens, Zachary K.; Grubbs, Robert H.; Angewandte Chemie - International Edition; vol. 52; nb. 10; (2013); p. 2944 - 2948; Angew. Chem.; (2013); p. 3016 - 3020 View in Reaxys

46 %, 45 %

4.6 : Example 4.3 [0122] General Procedure 2 (Table 2 and Scheme 1): Palladium acetate (11.5 mg, 0.05 mmol, 5 mol percent) and benzoquinone (108 mg, 1.00 mmol) were charged in a resealable 20-mL vial under air. A mixture of DMA (2.2 mL), MeCN (2.2 mL) and

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water (0.63 mL) was added, followed by the addition of aqueous HBF4 (0.18 mL, 48percent in water, 1.38 mmol). After the addition of the corresponding substrate (1.00 mmol), the homogenous reaction mixture was stirred for 16 h at room temperature. The crude reaction mixture was then diluted with brine (30 mL) and ether (30 mL), the phases were separated and the aqueous phase was further extracted (2×) with ether. The combined organic phases were then dried over Na2SO4, filtered, and evaporated in vacuo. In some cases, NMR-analysis of the crude mixture was performed to determine the regioselectivity of the process. The crude product was then further purified by column chromatography on silica gel using pentane/ether as eluent. [0129] Propiophenone and phenyl acetone (Table 2, Entry 6) were obtained from trans-η-methyl styrene following a modified General Procedure 2 using MeCN/ H2O (4.4 mL/0.63 mL) as the solvent. Crude ratio by NMR was 1:1. The products could be separated by column chromatography, giving two clear oils (A: 62 mg, 0.46 mmol, 46percent and B: 60 mg, 0.45 mmol, 45percent). A: 1H NMR: 7.98-7.94 (m, 2H), 7.57-7.52 (m, 1H), 7.48-7.43 (m, 2H), 3.00 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H). 13C NMR: η 200.8, 136.9, 132.9, 128.5, 128.0, 31.8, 8.2. B: 1H NMR: η 7.36-7.32 (m, 2H), 7.30-7.25 (m, 1H), 7.23-7.19 (m, 2H), 3.70 (s, 2H), 2.15 (s, 3H). 13C NMR: η 206.3, 134.2, 129.4, 128.8, 127.1, 51.0, 29.3. Values were in accordance with a commercial sample. With tetrafluoroboric acid, water, palladium diacetate, p-benzoquinone in acetonitrile, Time= 16h, T= 20 °C Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; MORANDI, Bill; GRUBBS, Robert H.; WICKENS, Zachary K.; US2014/194604; (2014); (A1) English View in Reaxys With water, oxygen, copper(l) iodide, palladium dichloride in N,N-dimethyl-formamide, Time= 24h, T= 50 °C , Wacker oxidation, Title compound not separated from byproducts. Gaunt; Yu; Spencer; Chemical Communications; nb. 18; (2001); p. 1844 - 1845 View in Reaxys O O

Rx-ID: 35100987 View in Reaxys 81/824 Yield 56 %, 35 %

56 %, 35 %

4.7 : Example 4.7 [0122] General Procedure 2 (Table 2 and Scheme 1): Palladium acetate (11.5 mg, 0.05 mmol, 5 mol percent) and benzoquinone (108 mg, 1.00 mmol) were charged in a resealable 20-mL vial under air. A mixture of DMA (2.2 mL), MeCN (2.2 mL) and water (0.63 mL) was added, followed by the addition of aqueous HBF4 (0.18 mL, 48percent in water, 1.38 mmol). After the addition of the corresponding substrate (1.00 mmol), the homogenous reaction mixture was stirred for 16 h at room temperature. The crude reaction mixture was then diluted with brine (30 mL) and ether (30 mL), the phases were separated and the aqueous phase was further extracted (2×) with ether. The combined organic phases were then dried over Na2SO4, filtered, and evaporated in vacuo. In some cases, NMR-analysis of the crude mixture was performed to determine the regioselectivity of the process. The crude product was then further purified by column chromatography on silica gel using pentane/ether as eluent. [0130] Propiophenone and phenyl acetone (Table 2, Entry 7) were obtained from cis-η-methyl styrene following a modified General Procedure 2 using MeCN/H2O (4.4 mL/0.63 mL) as the solvent. Crude ratio by NMR was 1.4:1 (A:B). The products could be separated by column chromatography, giving two clear oils (A: 75 mg, 0.56 mmol, 56percent and B: 47 mg, 0.35 mmol, 35percent). A: 1H NMR: 7.98-7.94 (m, 2H), 7.57-7.52 (m, 1H), 7.48-7.43 (m, 2H), 3.00 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H). 13C NMR: η 200.8, 136.9, 132.9, 128.5, 128.0, 31.8, 8.2. B: 1H NMR: η 7.36-7.32 (m, 2H), 7.30-7.25 (m, 1H), 7.23-7.19 (m, 2H), 3.70 (s, 2H), 2.15 (s, 3H). 13C NMR: η 206.3, 134.2, 129.4, 128.8, 127.1, 51.0, 29.3. Values were in accordance with a commercial sample. With tetrafluoroboric acid, water, palladium diacetate, p-benzoquinone in acetonitrile, Time= 16h, T= 20 °C Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; MORANDI, Bill; GRUBBS, Robert H.; WICKENS, Zachary K.; US2014/194604; (2014); (A1) English View in Reaxys

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O O

Rx-ID: 37118261 View in Reaxys 82/824 Yield

Conditions & References

65 %

With ammonium peroxydisulfate, dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer in water, Time= 3h, T= 110 °C , Inert atmosphere, Sealed tube Li, Yang; Xue, Dong; Lu, Wei; Wang, Chao; Liu, Zhao-Tie; Xiao, Jianliang; Organic Letters; vol. 16; nb. 1; (2014); p. 66 69 View in Reaxys O

Rx-ID: 37118283 View in Reaxys 83/824 Yield

Conditions & References

63 %

H 2N

NH 2

HO O

Rx-ID: 37304899 View in Reaxys 84/824 Yield

Conditions & References 2.9. Kinetic resolution of racemic amines General procedure: Racemic amine (10 mM, Table 4) was mixed with glyoxylate (10 mM) in 1 ml of phosphate buffer (100 mM, pH 7.4) containing PLP (20 μM). The reaction was started by adding 0.8 mg/ml of HBV-η-TA, and the mixture was incubated at 37 °C for 12 h. The amount and ee value of the residual amino donor were determined according to Section 2.10. With pyridoxal 5'-phosphate, recombinant η-transaminase from Burkholderia vietnamiensis G4 in aq. buffer, Time= 12h, T= 37 °C , pH= 7.4, Resolution of racemate, Enzymatic reaction, enantioselective reaction Jiang, Jinju; Chen, Xi; Feng, Jinhui; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 100; (2014); p. 32 - 39 View in Reaxys

NH 2

HO NH 2 O

Rx-ID: 37304911 View in Reaxys 85/824 Yield

Conditions & References 2.7. Substrate specificity and enantioselectivity

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General procedure: Amino donor specificity was assayed by following the similar procedure of Section 2.5. The amino donor substrates (10 mM) listed in Table 1 reacted with pyruvate (10 mM) as amino acceptor. For racemic amino donor, the concentration was 20 mM. After the reaction, residual pyruvate was analyzed by HPLC according to Section 2.10. Amino acceptor specificity was assayed by following the similar procedure of Section 2.5. The amino acceptor substrates (10 mM) listed in Table 2 reacted with (S)-η-MBA (10 mM) as amino donor. After the reaction, the amount of produced acetophenone was analyzed and the ee values of the produced amines were determined according to Section 2.10. With pyridoxal 5'-phosphate, recombinant η-transaminase from Burkholderia vietnamiensis G4 in aq. phosphate buffer, Time= 0.0833333h, T= 37 °C , pH= 7.4, Enzymatic reaction, enantioselective reaction Jiang, Jinju; Chen, Xi; Feng, Jinhui; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 100; (2014); p. 32 - 39 View in Reaxys OH O

Rx-ID: 37333757 View in Reaxys 86/824 Yield

Conditions & References 1 : Example 1 : 1 - (3,4-dimethoxyphenyl) -2 - (2 -methoxyphenoxy)propane- 1 ,3-diol. Example 1 : 1 - (3,4-dimethoxyphenyl) -2 - (2 -methoxyphenoxy)propane- 1 ,3-diol. Raney Ni 4200 ( 17 mg, 3.4 x 10 4 mol, 20 molpercent) is weighed into a reaction flask. Ethyl acetate (4 mL), isopropanol (20 μ^, 2 x 10 4 mol) and l-(3,4-dimethoxyphenyl)- 2-(2-methoxyphenoxy)propane- l,3-diol (1.6 x 10 4 mol, 54 mg), is added and the reaction flask is capped with a rubber septa and the mixture is heated (100 °C). The reaction is run for 24 hours and the reaction mixture is filtered. The phenol is extracted with Na2C03, the solvents are evaporated and the product is purified by column chromatography. The products was analyzed by and 13C NMR spectroscopy and corresponded to a 1 : 1 : 1 mixture of l-phenylpropane- l,3-diol, propiophenone, and l-cyclohexylpropane- l,3-diol in above 95percent yield. With isopropyl alcohol in ethyl acetate, Time= 24h, T= 100 °C , Overall yield = > 95 percentSpectr. Patent; KAT2BIZ AB; SAMEC, Joseph; GALKIN, Maxim; WO2014/38989; (2014); (A1) English View in Reaxys

OH N N

Rx-ID: 37443693 View in Reaxys 87/824 Yield

Conditions & References Reaction Steps: 2 1: azide(1-) / N,N-dimethyl-formamide 2: yeast strain Pichia sp. CR / 48 h / 28 °C / Microbiological reaction; Enzymatic reaction With azide(1-) in N,N-dimethyl-formamide Coronel, Camila; Arce, Gabriel; Iglesias, Cesar; Noguera, Cynthia Magallanes; Bonnecarrere, Paula Rodriguez; Giordano, Sonia Rodriguez; Gonzalez, David; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 94 - 98 View in Reaxys

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Cl HO

Rx-ID: 37443694 View in Reaxys 88/824 Yield

Conditions & References 2.2.1. General procedure for biotransformations with yeast strains General procedure: Fresh plates of each yeast strain were streaked from the frozen stock in PDA. A single colony was used to inoculate 100mL of YM Broth. The culture was incubated at 28°C and 150rpm for 48h and the cells were collected by centrifugation at 4000rpm and 4°C for 15min. The pellet was washed three times with 50mL physiological serum. Afterward, 2g of yeast cells (wet weight) were suspended in 20mL of 10percent dextrose solution and 30mg of the appropriate substrate were added. The culture was incubated at 28°C and 150rpm in an orbital shaker ZHICHENG ZHWY-211B for 48h. With yeast strain Aureobasidium pullulans CQA, Time= 48h, T= 28 °C , Microbiological reaction, Enzymatic reaction Coronel, Camila; Arce, Gabriel; Iglesias, Cesar; Noguera, Cynthia Magallanes; Bonnecarrere, Paula Rodriguez; Giordano, Sonia Rodriguez; Gonzalez, David; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 94 - 98 View in Reaxys

30 %Chromat., 23 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Candida viswanathii KCh 120 in acetone, Time= 6h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

Cl HO

Rx-ID: 37443695 View in Reaxys 89/824 Yield

Conditions & References 2.2.1. General procedure for biotransformations with yeast strains General procedure: Fresh plates of each yeast strain were streaked from the frozen stock in PDA. A single colony was used to inoculate 100mL of YM Broth. The culture was incubated at 28°C and 150rpm for 48h and the cells were collected by centrifugation at 4000rpm and 4°C for 15min. The pellet was washed three times with 50mL physiological serum. Afterward, 2g of yeast cells (wet weight) were suspended in 20mL of 10percent dextrose solution and 30mg of the appropriate substrate were added. The culture was incubated at 28°C and 150rpm in an orbital shaker ZHICHENG ZHWY-211B for 48h. With yeast strain Rhodotorula glutinis H93, Time= 48h, T= 28 °C , Microbiological reaction, Enzymatic reaction

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Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Rhodotorula rubra KCh 82 in acetone, Time= 24h, T= 25 °C , Microbiological reaction, Reagent/catalyst, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys O

N N N

Rx-ID: 37443699 View in Reaxys 90/824 Yield

Conditions & References 2.1 Biotransformations with D. carota roots General procedure: Edible carrot (D. carota) roots were purchased in a local market in Montevideo, Uruguay. The roots were thoroughly washed with running tap water and the external layer was removed with a sterile knife. Then, the plant tissue was washed with sterile distilled water, disinfected with 10percent sodium hypochlorite solution for 3min, and rinsed with sterile distilled water. Next, the plant parts were soaked in 70percent aq. ethanol for 3min and rinsed three times with sterile distilled water. Disinfected plant tissues were sliced with a sterile knife. Immediately, 90g of plant fragments were transferred to a 250mL sterile Erlenmeyer flask and suspended in 100mL of sterile water containing 90mg of the appropriate substrate. The culture was incubated at 28°C and 150rpm in a ZHICHENG ZHWY-211B orbital shaker for 48h. With Carrot (Daucus carota), Time= 48h, T= 28 °C , Microbiological reaction, Enzymatic reaction Coronel, Camila; Arce, Gabriel; Iglesias, Cesar; Noguera, Cynthia Magallanes; Bonnecarrere, Paula Rodriguez; Giordano, Sonia Rodriguez; Gonzalez, David; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 94 - 98 View in Reaxys

N N

Rx-ID: 37443700 View in Reaxys 91/824 Yield

Conditions & References 2.2.1. General procedure for biotransformations with yeast strains General procedure: Fresh plates of each yeast strain were streaked from the frozen stock in PDA. A single colony was used to inoculate 100mL of YM Broth. The culture was incubated at 28°C and 150rpm for 48h and the cells were collected by centrifugation at 4000rpm and 4°C for 15min. The pellet was washed three times with 50mL physiological serum. Afterward, 2g of yeast cells (wet weight) were suspended in 20mL of 10percent dextrose solution and 30mg of the appropriate substrate were added. The culture was incubated at 28°C and 150rpm in an orbital shaker ZHICHENG ZHWY-211B for 48h. With yeast strain Pichia sp. CR, Time= 48h, T= 28 °C , Microbiological reaction, Enzymatic reaction Coronel, Camila; Arce, Gabriel; Iglesias, Cesar; Noguera, Cynthia Magallanes; Bonnecarrere, Paula Rodriguez; Giordano, Sonia Rodriguez; Gonzalez, David; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 94 - 98 View in Reaxys

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2.2.1. General procedure for biotransformations with yeast strains General procedure: Fresh plates of each yeast strain were streaked from the frozen stock in PDA. A single colony was used to inoculate 100mL of YM Broth. The culture was incubated at 28°C and 150rpm for 48h and the cells were collected by centrifugation at 4000rpm and 4°C for 15min. The pellet was washed three times with 50mL physiological serum. Afterward, 2g of yeast cells (wet weight) were suspended in 20mL of 10percent dextrose solution and 30mg of the appropriate substrate were added. The culture was incubated at 28°C and 150rpm in an orbital shaker ZHICHENG ZHWY-211B for 48h. With yeast strain Wickerhamomyces anomalus Z1, Time= 48h, T= 28 °C , Microbiological reaction, Enzymatic reaction, Reagent/catalyst Coronel, Camila; Arce, Gabriel; Iglesias, Cesar; Noguera, Cynthia Magallanes; Bonnecarrere, Paula Rodriguez; Giordano, Sonia Rodriguez; Gonzalez, David; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 94 - 98 View in Reaxys

(v5)

(v4) (v5) H (v5) C–

(v5)

(v4) (v5) H (v5) C–

(v5) (v5)

Ni 2+ (v3) N C – (v7) N H

Ni 2+ (v3)

–Br (v1)

(v7)

N N

(v4)

Rx-ID: 37570696 View in Reaxys 92/824 Yield

Conditions & References

21 %, 63 %

in toluene, Time= 24h, T= 110 °C , Schlenk technique, Inert atmosphere Henrion, Mickael; Chetcuti, Michael J.; Ritleng, Vincent; Chemical Communications; vol. 50; nb. 35; (2014); p. 4624 - 4627 View in Reaxys O O

Rx-ID: 38066536 View in Reaxys 93/824 Yield

Conditions & References General procedure for the oxidation of alcohols with molecular iodine and potassium tertbutoxide General procedure: (Tables 1 and 2, Scheme 1). In a typical run, a reaction flask (25 mL) was chargedwith an indicated amount of I2 (typically, 508 mg, 2 mmol) and potassium tert-butoxide(typically, 470 mg, 4.2 mmol). The mixture was suspended in CH2Cl2 (5 mL) and stirred at 10 oCfor 30 min, then alcohol (1 mmol) was added. The mixture was continually stirred at an indicatedtemperature (typically, at 10 °C) until the consumption of the alcohol (monitoring with TLC,typically, for a few hours), then diluted with CH2Cl2 (10 mL) and washed with saturated aqueoussodium thiosulfate (10 mL). The aqueous phase was extracted with CH2Cl2 (three portions of 10mL each). The combined organic phase was washed with deionized water and saturated aqueousNaCl, dried over anhydrous Na2SO4, and then filtered and concentrated. The crude product waspurified by column chromatography (silica, hexane or hexane/EtOAc mixture as eluent). Theyields are listed in Tables 1 and 2 as well as Scheme 1. With potassium tert-butylate, iodine in dichloromethane, Time= 3h, T= 10 °C , Overall yield = 60 percent Luo, Qun-Li; Nan, Wen-Hui; Li, Yu; Chen, Xiang; Arkivoc; vol. 2014; nb. 4; (2014); p. 350 - 361 View in Reaxys

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Rx-ID: 38415005 View in Reaxys 94/824 Yield

Conditions & References

93 %

With Oxone, potassium bromide in acetonitrile, Time= 24.5h, T= 0 - 30 °C , Green chemistry Moriyama, Katsuhiko; Nakamura, Yu; Togo, Hideo; Organic Letters; vol. 16; nb. 14; (2014); p. 3812 - 3815 View in Reaxys

O O

O HO

Rx-ID: 38463890 View in Reaxys 95/824 Yield

Conditions & References

12 %, 5 %, 5 %, 40 %

With tert.-butylhydroperoxide, manganese(II) acetate, trifluoroacetic acid in acetonitrile, Time= 21h, T= 80 °C , p= 15001.5Torr , Mechanism, chemoselective reaction Raeisaenen, Minna T.; Al-Hunaiti, Afnan; Atosuo, Elisa; Kemell, Marianna; Leskelae, Markku; Repo, Timo; Catalysis Science and Technology; vol. 4; nb. 8; (2014); p. 2564 - 2573 View in Reaxys

O HO

Rx-ID: 39087132 View in Reaxys 96/824 Yield

Conditions & References With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, potassium tert-butylate, lithium chloride, t-butyl [(S)-1-((S)-2-hydroxypropylcarbamoyl)ethyl]carbamate in tetrahydrofuran, propan-1-ol, Time= 3h, T= 40 °C , Inert atmosphere, Concentration, enantioselective reaction Slagbrand, Tove; Lundberg, Helena; Adolfsson, Hans; Chemistry - A European Journal; vol. 20; nb. 49; (2014); p. 16102 16106 View in Reaxys

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O OH

H O

Rx-ID: 39087136 View in Reaxys 97/824 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; t-butyl [(S)-1-((S)-2-hydroxypropylcarbamoyl)ethyl]carbamate; lithium chloride; potassium tert-butylate / tetrahydrofuran; ethanol / 3 h / 40 °C / Inert atmosphere With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, potassium tert-butylate, lithium chloride, t-butyl [(S)-1-((S)-2-hydroxypropylcarbamoyl)ethyl]carbamate in tetrahydrofuran, ethanol Slagbrand, Tove; Lundberg, Helena; Adolfsson, Hans; Chemistry - A European Journal; vol. 20; nb. 49; (2014); p. 16102 16106 View in Reaxys

O H

Rx-ID: 39087137 View in Reaxys 98/824 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; t-butyl [(S)-1-((S)-2-hydroxypropylcarbamoyl)ethyl]carbamate; lithium chloride; potassium tert-butylate / tetrahydrofuran; propan-1-ol / 3 h / 40 °C / Inert atmosphere With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, potassium tert-butylate, lithium chloride, t-butyl [(S)-1-((S)-2-hydroxypropylcarbamoyl)ethyl]carbamate in tetrahydrofuran, propan-1-ol Slagbrand, Tove; Lundberg, Helena; Adolfsson, Hans; Chemistry - A European Journal; vol. 20; nb. 49; (2014); p. 16102 16106 View in Reaxys O OH

Cl HO

Rx-ID: 39115174 View in Reaxys 99/824

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Yield

Conditions & References

21 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Aphanocladium album KCh 417 in acetone, Time= 144h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

33 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Saccharomyces cerevisiae KCh 464 in acetone, Time= 144h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

33 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Saccharomyces pastorianus KCh 906 in acetone, Time= 24h, T= 25 °C , Microbiological reaction, Reagent/catalyst, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys O

OH H

Cl HO

Rx-ID: 39115175 View in Reaxys 100/824

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Yield

Conditions & References

7 %Chromat., 21 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Rhodotorula rubra KCh 4 in acetone, Time= 24h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys O

OH H

Rx-ID: 39115176 View in Reaxys 101/824 Yield 29 %Chromat., 33 %Chromat.

Conditions & References Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Candida parapsilosis KCh 909 in acetone, Time= 72h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

28 %Chromat., 57 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Candida viswanathii KCh 120 in acetone, Time= 144h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

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Rx-ID: 39115177 View in Reaxys 102/824 Yield

Conditions & References

61 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Saccharomyces brasiliensis KCh 905 in acetone, Time= 24h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

O OH

H HO

Rx-ID: 39115179 View in Reaxys 103/824 Yield 32 %Chromat.

Conditions & References Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Rhodotorula rubra KCh 4 in acetone, Time= 216h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

8 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Yarrowia lipolytica 1-101-1,31-K1 in acetone, Time= 216h, T= 25 °C , Microbiological reaction, Reagent/ catalyst, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

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58 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Yarrowia lipolytica ATCC 32-338 A in acetone, Time= 72h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys

Cl HO

Rx-ID: 39115180 View in Reaxys 104/824 Yield

Conditions & References

34 %Chromat., 6 %Chromat., 60 %Chromat.

Screening procedure General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times. With yeast culture of Rhodotorula rubra KCh 82 in acetone, Time= 6h, T= 25 °C , Microbiological reaction, enantioselective reaction Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys O

N S–

Na +

Rx-ID: 39123138 View in Reaxys 105/824 Yield

Conditions & References

89%

With palladium(II) trifluoroacetate, trifluoroacetic acid, 6-methyl-2,2'-bipyridine in tetrahydrofuran, water, Time= 1h, T= 100 °C , Microwave irradiation Skillinghaug, Bobo; Sköld, Christian; Rydfjord, Jonas; Svensson, Fredrik; Behrends, Malte; Sävmarker, Jonas; Sjöberg, Per J. R.; Larhed, Mats; Journal of Organic Chemistry; vol. 79; nb. 24; (2014); p. 12018 - 12032 View in Reaxys O O

S Cl

Rx-ID: 39123229 View in Reaxys 106/824

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Yield

Conditions & References Reaction Steps: 2 1: sodium sulfite; sodium hydrogencarbonate / water / 3 h / Reflux 2: palladium(II) trifluoroacetate; 6-methyl-2,2'-bipyridine; trifluoroacetic acid / water; tetrahydrofuran / 1 h / 100 °C / Microwave irradiation With palladium(II) trifluoroacetate, sodium hydrogencarbonate, trifluoroacetic acid, sodium sulfite, 6-methyl-2,2'-bipyridine in tetrahydrofuran, water Skillinghaug, Bobo; Sköld, Christian; Rydfjord, Jonas; Svensson, Fredrik; Behrends, Malte; Sävmarker, Jonas; Sjöberg, Per J. R.; Larhed, Mats; Journal of Organic Chemistry; vol. 79; nb. 24; (2014); p. 12018 - 12032 View in Reaxys O

O O Si

Rx-ID: 39684610 View in Reaxys 107/824 Yield

Conditions & References

7 %Chromat., 7 %Chromat.

With oxygen in toluene, Time= 15h, T= 80 °C , p= 760.051Torr Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys

O Si

Rx-ID: 39684611 View in Reaxys 108/824 Yield

Conditions & References

11 %Chro- With oxygen in water, toluene, Time= 15h, T= 60 °C , p= 760.051Torr , Time, Solvent mat., 7 %Chromat., Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 26 %Chro- View in Reaxys mat., 15 %Chromat. O

O O Si

Rx-ID: 39684612 View in Reaxys 109/824 Yield 6 %Chromat., 25 %Chromat., 28 %Chromat.

Conditions & References 4.5.4. A typical procedure for aerobic oxidation of silyl enol ethercatalyzed by PI-Au 4l. General procedure: 4.5.4. A typical procedure for aerobic oxidation of silyl enol ether catalyzed by PI-Au 4l. Trimethyl(1-phenylprop-1-enyloxy)silane (51.5 mg, 0.25 mmol), PI-Au 4l (0.240 mmol/g, 1 mol percent), toluene (1.0 mL), and water (1.0 mL) were combined in a round-bottom flask. The mixture was stirred for 11 h under O2 at 80 °C. After cooling to room temperature, the catalyst was collected by filtration and washed with ethyl acetate, using a Kiriyamarohto funnel. The aqueous layer was extracted with ethyl acetate (20-30 mL). The combined organic layers were dried over sodium sulfate. The yield was determined by GC analysis with reference to an internal standard (anisole).

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With oxygen in water, toluene, Time= 11h, T= 80 °C , p= 760.051Torr , Time, Temperature Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys O

Rx-ID: 39684614 View in Reaxys 110/824 Yield

Conditions & References

89 %Chromat.

With oxygen in water, toluene, Time= 14h, T= 100 °C , p= 760.051Torr , Time, Temperature, Solvent Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys O

Rx-ID: 39684615 View in Reaxys 111/824 Yield

Conditions & References

16 %Chro- With oxygen in water, toluene, Time= 16h, T= 100 °C , p= 760.051Torr , Time, Temperature, Solvent mat., 30 %Chromat., Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 16 %Chro- View in Reaxys mat. O O

Rx-ID: 39684616 View in Reaxys 112/824 Yield

Conditions & References

27 %Chromat., 12 %Chromat.

With oxygen in N,N-dimethyl-formamide, Time= 12h, T= 80 °C , p= 760.051Torr , Solvent Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys O

Rx-ID: 39865290 View in Reaxys 113/824 Yield 31 %

Conditions & References With oxygen, copper diacetate, potassium carbonate, aniline in dimethyl sulfoxide, T= 120 °C , Schlenk technique, Sealed tube, chemoselective reaction Gu, Lijun; Jin, Cheng; Zhang, Hongtao; Zhang, Lizhu; Journal of Organic Chemistry; vol. 79; nb. 17; (2014); p. 8453 - 8456 View in Reaxys

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Br O

Rx-ID: 34809542 View in Reaxys 114/824 Yield

Conditions & References

90 %, 8 %

With C24H38N2O6, palladium diacetate in water, Time= 6h, T= 60 °C , Inert atmosphere, Reagent/catalyst Kuroboshi, Manabu; Yamamoto, Takashi; Tanaka, Hideo; Synlett; vol. 24; nb. 2; (2013); p. 197 - 200; Art.No: ST-2012U0872-L View in Reaxys

17 %, 25 %

With palladium diacetate, 1,1'-dimethyl-1,1'-dihydro-4,4'-bipyridyl in water, Time= 4h, T= 60 °C , Inert atmosphere, Reagent/ catalyst Kuroboshi, Manabu; Yamamoto, Takashi; Tanaka, Hideo; Synlett; vol. 24; nb. 2; (2013); p. 197 - 200; Art.No: ST-2012U0872-L View in Reaxys

19 A typical procedure of the electroreductive coupling of aryl bromide1 with catalytic amounts of [OctV2+][Tf2N]2 and Pd spe%Spectr., cies isas follows. Into an undivided cell fitted with a Zn anode(1.5 1 cm2) and a Pt cathode (1.5 1 cm2) was added a DMF(3 mL) 15 %Spectr. solution of 4-bromopropiophenone (1a, 0.25 mmol),[Bu4N+][Tf2N] (0.3 mmol), [OctV2+][Tf2N]2 (0.075 mmol,30 mol percent), and PdCl2(PPh3)2 (0.0125 mmol, 5 mol percent). The wholemixture was electrolyzed at 60 C under constant current(10 mA) conditions until 2 F/mol—1a of electricity was passed.The reaction mixture was poured into 5percent aq HCl and extractedwith AcOEt. Purification by column chromatography (SiO2, toluene/AcOEt = 10/1) afforded 4,40-dipropanoylbiphenyl (2a) in 94percentyield With bis-triphenylphosphine-palladium(II) chloride, 1,1'-dioctyl-4,4'-bipyridinium bis(trifluimide), tetrabutylammonium bis(trifluoromethanesulfonyl)imide in tetrahydrofuran, T= 60 °C , Electrochemical reaction Kuroboshi, Manabu; Shiba, Takuya; Tanaka, Hideo; Tetrahedron Letters; vol. 54; nb. 28; (2013); p. 3666 - 3668 View in Reaxys O HO

H 2N

Rx-ID: 35100300 View in Reaxys 115/824 Yield 28 %Chromat., 13 %Chromat.

Conditions & References With alanine dehydrogenase, (S)-η-alanine, pyridoxal 5'-phosphate, NAD, ammonium chloride, alcohol dehydrogenase in aq. phosphate buffer, Time= 24h, T= 30 °C , Enzymatic reaction Tauber, Katharina; Fuchs, Michael; Sattler, Johann H.; Pitzer, Julia; Pressnitz, Desiree; Koszelewski, Dominik; Faber, Kurt; Pfeffer, Jan; Haas, Thomas; Kroutil, Wolfgang; Chemistry - A European Journal; vol. 19; nb. 12; (2013); p. 4030 4035 View in Reaxys O

Rx-ID: 35163063 View in Reaxys 116/824 Yield

Conditions & References

5.5 %, 60 % With hydrogenchloride, water, cetyltrimethylammonim bromide in isopropyl alcohol, Time= 48h, T= 140 °C Nairoukh, Zackaria; Avnir, David; Blum, Jochanan; ChemSusChem; vol. 6; nb. 3; (2013); p. 430 - 432

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View in Reaxys

O–

I+ O

S F O

O O

Rx-ID: 35433397 View in Reaxys 117/824 Yield

Conditions & References With water, oxygen, copper diacetate in dichloromethane, Time= 3h, T= 80 °C , regioselective reaction Xu, Ze-Feng; Cai, Chen-Xin; Liu, Jin-Tao; Organic Letters; vol. 15; nb. 9; (2013); p. 2096 - 2099 View in Reaxys

O–

I+ O

–O

O Cu 2+

F O

O F

F S

S O

O O

F F

O F

S F

O F

Conditions & References With water, oxygen in dichloromethane, Time= 3h, T= 80 °C , regioselective reaction Xu, Ze-Feng; Cai, Chen-Xin; Liu, Jin-Tao; Organic Letters; vol. 15; nb. 9; (2013); p. 2096 - 2099 View in Reaxys O

Rx-ID: 35749764 View in Reaxys 119/824 70 %

O F

Rx-ID: 35433398 View in Reaxys 118/824

Yield

Conditions & References With (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, oxygen in hexane, Time= 4h, T= 150 °C , p= 15001.5Torr

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Sheng, Wen-Bing; Jiang, Qing; Luo, Wei-Ping; Guo, Can-Cheng; Journal of Organic Chemistry; vol. 78; nb. 11; (2013); p. 5691 - 5693 View in Reaxys

S O

S HO

Rx-ID: 35806641 View in Reaxys 120/824 Yield

Conditions & References

34 %

With iron(II) chloride tetrahydrate in 1,2-dichloro-ethane, Time= 3h, T= 60 °C Park, Jungmin; Yeon, Jihee; Lee, Phil Ho; Lee, Kooyeon; Tetrahedron Letters; vol. 54; nb. 33; (2013); p. 4414 - 4417 View in Reaxys

O O

S O

Rx-ID: 35806645 View in Reaxys 121/824 Yield

Conditions & References

100 %

With methanesulfonic acid in 1,2-dichloro-ethane, Time= 1h, T= 60 °C Park, Jungmin; Yeon, Jihee; Lee, Phil Ho; Lee, Kooyeon; Tetrahedron Letters; vol. 54; nb. 33; (2013); p. 4414 - 4417 View in Reaxys

HO N N

Rx-ID: 36051842 View in Reaxys 122/824 Yield

Conditions & References

52 %

With hydrogenchloride in chloroform, water, Time= 4h, Reflux Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935 View in Reaxys O HO

Rx-ID: 36371741 View in Reaxys 123/824 Yield 56 %

Conditions & References General procedure for the acylodeboronation reaction of arylboronic acids with aceticanhydride. General procedure: A 5 mL flask charged with acetic anhydride (1.0 mmol), arylboronic acid (0.5mmol), KHCO3 (1.0 mmol), complex 1 (0.5 molpercent, 3.1 mg), PPh3 (0.01 mmol, 1.3 mg) andtoluene (2.0 mL) was evacuated and backfilled with N2 for

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three times before the reaction wasput into a preheated 110 oC oil bath. After the reaction was finished in 3h, the reaction mixture was cooled to room temperature, filtered through a short silica column and washed with ethylacetate. Then the combined filtrates were concentrated in vacuo and the residue was purified byflash chromatography (eluent: ethylacetate/petroleum ether). All the products were knowncompounds and characterized by comparing mp, 1H NMR and 13C NMR spectra with literature. With 2C60H80NaO12 (2+)*Cl6Pd2 (2-), potassium hydrogencarbonate, triphenylphosphine in toluene, Time= 3h, T= 110 °C , Inert atmosphere Zhang, Jinli; Han, Zixing; Li, Junmiao; Wu, Yangjie; Arkivoc; vol. 2013; nb. 4; (2013); p. 251 - 271 View in Reaxys O O

O Br

Br Br

Rx-ID: 36727615 View in Reaxys 124/824 Yield

Conditions & References

93 %

With tris-(trimethylsilyl)silane in acetonitrile, Time= 24h, Schlenk technique, Inert atmosphere, Irradiation Jiang, Hao; Bak, Jesper R.; Lopez-Delgado, Francisco Javier; Jorgensen, Karl Anker; Green Chemistry; vol. 15; nb. 12; (2013); p. 3355 - 3359 View in Reaxys O

Rx-ID: 36988170 View in Reaxys 125/824 Yield

Conditions & References With tert.-butylhydroperoxide, {[Cu(isonicotinate)2(H2O)][Cu(isonicotinate)2(4,4’-bipyridine)]}n, oxygen in water, acetonitrile, Time= 8h, T= 50 °C , p= 760.051Torr , Concentration Saha, Rajat; Joarder, Biplab; Roy, Anupam Singha; Manirul Islam, Sk.; Kumar, Sanjay; Chemistry - A European Journal; vol. 19; nb. 49; (2013); p. 16607 - 16614 View in Reaxys O HO

Rx-ID: 37034781 View in Reaxys 126/824 Yield

Conditions & References in neat (no solvent, solid phase), T= 373 °C , Temperature Tang, Yibo; Li, Zenghua; Ma, Dongjuan; Liu, Zhen; Asian Journal of Chemistry; vol. 25; nb. 15; (2013); p. 8677 - 8680 View in Reaxys

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O OH O

Rx-ID: 37200523 View in Reaxys 127/824 Yield

Conditions & References

0.07 mol, 0.1 mol, 0.08 mol, 0.03 mol, 0.2 mol, 0.07 mol

With tert.-butylhydroperoxide, chromium tetra(tert-butoxide) in benzene Stepovik; Potkina; Poddelskii; Russian Journal of General Chemistry; vol. 83; nb. 11; (2013); p. 2005 - 2017; Zh. Obshch. Khim.; vol. 83; nb. 11; (2013); p. 1805 - 1818,14 View in Reaxys

Rx-ID: 37200524 View in Reaxys 128/824 Yield

Conditions & References Reaction Steps: 2 1: dihydrogen peroxide; sulfuric acid / diethyl ether / 0 - 5 Â°C 2: chromium tetra(tert-butoxide) / benzene With sulfuric acid, dihydrogen peroxide, chromium tetra(tert-butoxide) in diethyl ether, benzene Stepovik; Potkina; Poddelskii; Russian Journal of General Chemistry; vol. 83; nb. 11; (2013); p. 2005 - 2017; Zh. Obshch. Khim.; vol. 83; nb. 11; (2013); p. 1805 - 1818,14 View in Reaxys

HO O

Rx-ID: 37200525 View in Reaxys 129/824 Yield

Conditions & References

0.4 mol, 0.29 mol, 0.16 mol, 0.09 mol, 0.05 mol

With chromium tetra(tert-butoxide) in benzene, Mechanism Stepovik; Potkina; Poddelskii; Russian Journal of General Chemistry; vol. 83; nb. 11; (2013); p. 2005 - 2017; Zh. Obshch. Khim.; vol. 83; nb. 11; (2013); p. 1805 - 1818,14 View in Reaxys O

HO O

Rx-ID: 5105849 View in Reaxys 130/824

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Yield

Conditions & References

95 %

With K5[CoIIIW12O40] in water, acetonitrile, Time= 0.166667h, Microwave irradiation Farhadi; Ansari; Journal of the Iranian Chemical Society; vol. 8; nb. 2; (2011); p. 470 - 476 View in Reaxys

94 %

With mercury(II) fluoride, oxygen in acetonitrile, Time= 24h, T= 25 °C , Irradiation Farhadi, Saeid; Zaringhadam, Parisa; Sahamieh, Reza Zarei; Tetrahedron Letters; vol. 47; nb. 12; (2006); p. 1965 - 1968 View in Reaxys

93 %

With meso-tetrakis(tetraphenyl)porphyrin iron(III) chloride, tetrabutylammonium periodite in dichloromethane, Time= 3h, Ambient temperature Tangestaninejad, Shahram; Mirkhani, Valiollah; Journal of Chemical Research - Part S; nb. 12; (1998); p. 820 - 821 View in Reaxys

93 %

With 1H-imidazole, sodium periodate, {Mn(III)[5,10,15,20-tetrakis(4-H2N-Ph)porphyrin]}polystyrene in acetonitrile, Time= 3h, T= 20 °C Mirkhani, Valiollah; Tangestaninejad, Shahram; Moghadam, Majid; Karimian, Zohreh; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 20; (2003); p. 3433 - 3435 View in Reaxys

93 %

With 1H-imidazole, sodium periodate, [Mn(III)-salophen]Cl in water, acetonitrile, Time= 0.0833333h, T= 20 °C Mirkhani, Valiollah; Tangestaninejad, Shahram; Moghadam, Majid; Moghbel, Maryam; Bioorganic and Medicinal Chemistry; vol. 12; nb. 5; (2004); p. 903 - 906 View in Reaxys

93 %

With 1H-imidazole, C17H16ClMnN2O2, tetrabutylammonium periodite in chloroform, Time= 0.666667h, T= 20 °C Montazerozohori; Nasr-Esfahani; Joohari; Akhlaghi; Dehghani; Asian Journal of Chemistry; vol. 23; nb. 3; (2011); p. 1081 - 1084 View in Reaxys

85 %

With sodium azide, [bis(acetoxy)iodo]benzene in acetonitrile, Time= 0.333333h, T= 0 - 20 °C Telvekar, Vikas N.; Sasane, Kulbhushan A.; Synlett; nb. 18; (2010); p. 2778 - 2780 View in Reaxys

74 %

With oxygen, mercury(II) oxide in methanol, acetonitrile, T= 25 °C , UV-irradiation Habibi, Mohammad H.; Farhadi, Saeid; Journal of Chemical Research; nb. 4; (2004); p. 296 - 297 View in Reaxys With 1H-imidazole, [bis(acetoxy)iodo]benzene, Co(AAOPD) in acetonitrile, T= 20 °C Soleymani, Reza; Taheri, Milad; HOSEYNALIBEYGl, Marziye; Daryani, Mehdi; Oriental Journal of Chemistry; vol. 28; nb. 2; (2012); p. 857 - 866,10 View in Reaxys

O HO

Rx-ID: 9310662 View in Reaxys 131/824 Yield 53 %

Conditions & References With Arthrobacter atrocyaneus in N,N-dimethyl-formamide, Time= 72h, T= 32 °C , Microbiological reaction, enantioselective reaction

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Silva, Camila R.; Souza, Juliana C.; Araujo, Lidiane S.; Kagohara, Edna; Garcia, Thais P.; Pelizzari, Vivian H.; Andrade, Leandro H.; Journal of Molecular Catalysis B: Enzymatic; vol. 83; (2012); p. 23 - 28 View in Reaxys With oxygen, caesium carbonate, (-)-sparteine, PdCl2(η4-NBD), 3 A molecular sieve in toluene, tert-butyl alcohol, Time= 4.5h, T= 80 °C , p= 760Torr Bagdanoff, Jeffrey T; Ferreira, Eric M; Stoltz, Brian M; Organic letters; vol. 5; nb. 6; (2003); p. 835 - 837 View in Reaxys With 3 A molecular sieve, oxygen, caesium carbonate, Pd(2,5-norbornadiene)Cl2, (-)-sparteine in chloroform, Time= 72h, T= 23 °C , p= 760Torr Bagdanoff, Jeffrey T.; Stoltz, Brian M.; Angewandte Chemie - International Edition; vol. 43; nb. 3; (2004); p. 353 - 357 View in Reaxys With [palladium(II)((-)-sparteine)dibromide], oxygen, caesium carbonate, (-)-sparteine in chloroform, Time= 24h, T= 4 °C , Molecular sieve, optical yield given as percent ee Ebner, David C.; Trend, Raissa M.; Genet, Cedric; McGrath, Matthew J.; O'Brien, Peter; Stoltz, Brian M.; Angewandte Chemie - International Edition; vol. 47; nb. 34; (2008); p. 6367 - 6370 View in Reaxys 3 :An 8 ml glass vial was charged with 1.2mg peptoid (7mers, lxlηηnol), 0.25 ml CH2Cl2, 0.125 ml of 0.5M KBr in water and lxlηηnol substrate (alcohol), placed in an ice bath and cooled to 0°C under stirring. The reaction started with the addition of 0.310 ml 0.5M NaOCl solution [1 equivalent of 1.8M NaOCl (that contains 10-13percent Cl) and 2.6 equivalents of water]. After two hours, 1 ml CH2Cl2 was added, the aqueous layer was separated and a sample from the CH2Cl2 solution was analyzed by GC. With sodium hypochlorite, potassium bromide, H-NtempoNrpeNpm(Nrpe)2NpmNrpe-NH2 in dichloromethane, water, Time= 2h, T= 0 °C , Product distribution / selectivity Patent; NEW YORK UNIVERSITY SCHOOL OF MEDICINE; WO2009/139922; (2009); (A2) English View in Reaxys With oxygen, caesium carbonate, (-)-sparteine in toluene, butan-1-ol, Time= 4.5h, T= 80 °C , p= 760.051Torr , Molecular sieve, optical yield given as percent ee Ebner, David C.; Bagdanoff, Jeffrey T.; Ferreira, Eric M.; McFadden, Ryan M.; Caspi, Daniel D.; Trend, Raissa M.; Stoltz, Brian M.; Chemistry - A European Journal; vol. 15; nb. 47; (2009); p. 12978 - 12992 View in Reaxys With bis(1,5-cyclooctadiene)diiridium(I) dichloride, bis(triphenylphosphine)iminium chloride, acetone, potassium hydroxide, N,N'-bis[o-(diphenylphosphino)benzylidene]-(1S,2S)-diaiminocyclohexane in dichloromethane, water, isopropyl alcohol, Time= 16h, T= 28 °C , Resolution of racemate, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Zhang, Juanni; Yang, Xiangren; Zhou, Han; Li, Yanyun; Dong, Zhenrong; Gao, Jingxing; Green Chemistry; vol. 14; nb. 5; (2012); p. 1289 - 1292 View in Reaxys O O

Rx-ID: 32504089 View in Reaxys 132/824 Yield 82 %Chromat., 6 %Chromat.

Conditions & References Typical procedure for the oxidation of secondary benzylic alcohols (Table 2). General procedure: To a mixture of alcohol 1 (1 mmol), tridecane (50 μL, 0.205 mmol, internal standard) and toluene (0.5 mL) in a screw cap tube was added t-BuONO (198 μL, 1.5 mmol, 1.5 equiv.) under N2 atmosphere. The solution was stirred at 120 °C for the indicated time in table 2. The reaction mixture was analyzed by GC and the product was isolated by column chromatography (SiO2) for the characterization. With tert.-butylnitrite in toluene, Time= 16h, T= 120 °C , Inert atmosphere

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Hamasaki, Akiyuki; Kuwada, Hideyuki; Tokunaga, Makoto; Tetrahedron Letters; vol. 53; nb. 7; (2012); p. 811 - 814 View in Reaxys

(v4)

CH –2

(v5) Rh 3+ – N – NN N (v3)(v4) (v4) (v3)

2 Rh 2+

O H N

(v4)Rh

N– (v3)

N–

2+(v5)–

(v3) (v4)

–N

Rx-ID: 32794458 View in Reaxys 133/824 Yield

Conditions & References

9 %Spectr., With water in benzene-d6, Time= 0.0833333h, T= 200 °C , Inert atmosphere, Darkness 18 Fung, Hong Sang; Li, Bao Zhu; Chan, Kin Shing; Organometallics; vol. 31; nb. 2; (2012); p. 570 - 579 %Spectr., 29 %Spectr. View in Reaxys

O O N

S HO

O S N H

O S

N H

Rx-ID: 33166189 View in Reaxys 134/824 Yield

Conditions & References With RuCl(CO2)(η5C5Ph5), potassium tert-butylate in tetrahydrofuran, toluene, Time= 15h, T= 35 °C , Inert atmosphere, Molecular sieve, Mannich type reaction, optical yield given as percent de, diastereoselective reaction Bartoszewicz, Agnieszka; Jezowska, Martina M.; Laymand, Kevin; Moebus, Juri; Martin-Matute, Belen; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1517 - 1530 View in Reaxys

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Rx-ID: 33166191 View in Reaxys 135/824 Yield

Conditions & References With RuCl(CO2)(η5C5Ph5), potassium tert-butylate in tetrahydrofuran, toluene, Time= 2.5h, T= 35 °C , Inert atmosphere, Molecular sieve, optical yield given as percent de, diastereoselective reaction Bartoszewicz, Agnieszka; Jezowska, Martina M.; Laymand, Kevin; Moebus, Juri; Martin-Matute, Belen; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1517 - 1530 View in Reaxys O

O S HO

O O

Rx-ID: 33166196 View in Reaxys 136/824 Yield

Conditions & References With RuCl(CO2)(η5C5Ph5), potassium tert-butylate in tetrahydrofuran, toluene, Time= 15h, T= 40 °C , Inert atmosphere, Molecular sieve, Mannich type reaction, optical yield given as percent de, diastereoselective reaction Bartoszewicz, Agnieszka; Jezowska, Martina M.; Laymand, Kevin; Moebus, Juri; Martin-Matute, Belen; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1517 - 1530 View in Reaxys O

O S HO

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O S

N H

Rx-ID: 33166197 View in Reaxys 137/824 Yield

Conditions & References With RuCl(CO2)(η5C5Ph5), potassium tert-butylate in tetrahydrofuran, Time= 30h, T= 40 °C , Inert atmosphere, Molecular sieve, Mannich type reaction, optical yield given as percent de, diastereoselective reaction Bartoszewicz, Agnieszka; Jezowska, Martina M.; Laymand, Kevin; Moebus, Juri; Martin-Matute, Belen; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1517 - 1530 View in Reaxys

H S N

O S

N H

Rx-ID: 33166198 View in Reaxys 138/824 Yield

Conditions & References With RuCl(CO2)(η5C5Ph5), potassium tert-butylate in tetrahydrofuran, toluene, Time= 11h, T= 40 °C , Inert atmosphere, Molecular sieve, Mannich type reaction, optical yield given as percent de, diastereoselective reaction Bartoszewicz, Agnieszka; Jezowska, Martina M.; Laymand, Kevin; Moebus, Juri; Martin-Matute, Belen; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1517 - 1530 View in Reaxys

N S O

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O S

N H

Rx-ID: 33166199 View in Reaxys 139/824 Yield

O S HO

O O

S O

Rx-ID: 33166200 View in Reaxys 140/824 Yield

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N H

Rx-ID: 33166201 View in Reaxys 141/824 Yield

Conditions & References With RuCl(CO2)(η5C5Ph5), potassium tert-butylate in tetrahydrofuran, toluene, Time= 15h, T= 35 °C , Inert atmosphere, Molecular sieve Bartoszewicz, Agnieszka; Jezowska, Martina M.; Laymand, Kevin; Moebus, Juri; Martin-Matute, Belen; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1517 - 1530 View in Reaxys O

Rx-ID: 33166203 View in Reaxys 142/824 Yield

Conditions & References With RuCl(CO2)(η5C5Ph5), potassium tert-butylate in tetrahydrofuran, toluene, Time= 15h, T= 35 - 100 °C , Inert atmosphere, diastereoselective reaction Bartoszewicz, Agnieszka; Jezowska, Martina M.; Laymand, Kevin; Moebus, Juri; Martin-Matute, Belen; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1517 - 1530 View in Reaxys

Rx-ID: 33166206 View in Reaxys 143/824 Yield

Conditions & References With RuCl(CO2)(η5C5Ph5), potassium tert-butylate, sodium carbonate in tetrahydrofuran, toluene, Time= 13h, T= 35 °C , Inert atmosphere Bartoszewicz, Agnieszka; Jezowska, Martina M.; Laymand, Kevin; Moebus, Juri; Martin-Matute, Belen; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1517 - 1530 View in Reaxys O

O S HO

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O S

N H

Rx-ID: 33166208 View in Reaxys 144/824 Yield

Conditions & References With RuCl(CO2)(η5C5Ph5), potassium tert-butylate in tetrahydrofuran, toluene, Time= 14h, T= 40 °C , Inert atmosphere, Molecular sieve, Mannich type reaction, optical yield given as percent de, diastereoselective reaction Bartoszewicz, Agnieszka; Jezowska, Martina M.; Laymand, Kevin; Moebus, Juri; Martin-Matute, Belen; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1517 - 1530 View in Reaxys O

Rx-ID: 33278348 View in Reaxys 145/824 Yield 100 %Spectr.

Conditions & References in methanol, Irradiation Griesbeck, Axel G.; Hinze, Olga; Goerner, Helmut; Huchel, Ursula; Kropf, Christian; Sundermeier, Uta; Gerke, Thomas; Photochemical and Photobiological Sciences; vol. 11; nb. 3; (2012); p. 587 - 592 View in Reaxys O

Rx-ID: 33278357 View in Reaxys 146/824 Yield

Conditions & References

90 in ethanol, Irradiation %Spectr., 10 %Spectr. Griesbeck, Axel G.; Hinze, Olga; Goerner, Helmut; Huchel, Ursula; Kropf, Christian; Sundermeier, Uta; Gerke, Thomas; Photochemical and Photobiological Sciences; vol. 11; nb. 3; (2012); p. 587 - 592 View in Reaxys O

Rx-ID: 33278367 View in Reaxys 147/824

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Yield

Conditions & References

95 %Spectr. in methanol, Irradiation Griesbeck, Axel G.; Hinze, Olga; Goerner, Helmut; Huchel, Ursula; Kropf, Christian; Sundermeier, Uta; Gerke, Thomas; Photochemical and Photobiological Sciences; vol. 11; nb. 3; (2012); p. 587 - 592 View in Reaxys OH

Rx-ID: 33278377 View in Reaxys 148/824 Yield 30 %Spectr., 60 %Spectr., 10 %Spectr.

Conditions & References in acetonitrile, Irradiation Griesbeck, Axel G.; Hinze, Olga; Goerner, Helmut; Huchel, Ursula; Kropf, Christian; Sundermeier, Uta; Gerke, Thomas; Photochemical and Photobiological Sciences; vol. 11; nb. 3; (2012); p. 587 - 592 View in Reaxys O

Rx-ID: 33284805 View in Reaxys 149/824 Yield

Conditions & References

79 %Spectr. With Pyridine-2,6-dicarboxylic acid, iron(II) tetrafluoroborate hexahydrate, iodosylbenzene in chloroform, Time= 20h, T= 20 °C , Molecular sieve, regioselective reaction Chowdhury, Abhishek Dutta; Ray, Ritwika; Lahiri, Goutam Kumar; Chemical Communications; vol. 48; nb. 44; (2012); p. 5497 - 5499 View in Reaxys O H

Rx-ID: 33284806 View in Reaxys 150/824 Yield

Conditions & References

75 %Spectr. With Pyridine-2,6-dicarboxylic acid, iron(II) tetrafluoroborate hexahydrate, iodosylbenzene in chloroform, Time= 20h, T= 20 °C , Molecular sieve, regioselective reaction Chowdhury, Abhishek Dutta; Ray, Ritwika; Lahiri, Goutam Kumar; Chemical Communications; vol. 48; nb. 44; (2012); p. 5497 - 5499 View in Reaxys

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Rx-ID: 33870674 View in Reaxys 151/824 Yield

Conditions & References

57 %Chromat.

With N-hydroxyphthalimide, oxygen in N,N-dimethyl acetamide, water, Time= 72h, T= 80 °C Lin, Riyuan; Chen, Feng; Jiao, Ning; Organic Letters; vol. 14; nb. 16; (2012); p. 4158 - 4161 View in Reaxys

OH H 2N

H 2N

O H

NH 2

NH 2 H

Rx-ID: 33885726 View in Reaxys 152/824 Yield

Conditions & References With (S)-selective η-transaminase from Ochrobactrum anthropi, L-threonine deaminase from Escherichia coli, pyridoxal 5'-phosphate, Time= 28h, T= 37 °C , pH= 7.5, aq. phosphate buffer, Resolution of racemate, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Malik, M. Shaheer; Park, Eul-Soo; Shin, Jong-Shik; Green Chemistry; vol. 14; nb. 8; (2012); p. 2137 - 2140 View in Reaxys

H 2N

H 2N H

NH 2 H

H OH

NH 2

Rx-ID: 33885727 View in Reaxys 153/824 Yield

Conditions & References With (S)-selective η-transaminase from Ochrobactrum anthropi, L-threonine deaminase from Escherichia coli, pyridoxal 5'-phosphate, Time= 30h, T= 37 °C , pH= 7.5, aq. phosphate buffer, Resolution of racemate, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Malik, M. Shaheer; Park, Eul-Soo; Shin, Jong-Shik; Green Chemistry; vol. 14; nb. 8; (2012); p. 2137 - 2140 View in Reaxys

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O O

Rx-ID: 33894128 View in Reaxys 154/824 Yield

Conditions & References 4.3. General photolysis procedure General procedure: A 1.x.10-4 m methanol/HEPES buffer (80:20) solution of conjugates 4 and 9 (5 mL) was placed in a quartz tube and irradiated in a Rayonet RPR-100 reactor at the desired wavelength. The lamps used for irradiation were of 300, 350 and 419+/-10 nm. HEPES buffer solution was prepared in distilled water with HEPES (4-(2-hydroxyethyl)-1-piperazine ethanesulfonic acid) (10 mM), sodium chloride (120 mM), potassium chloride (3 mM), calcium chloride (1 mM) and magnesium chloride (1 mM) and the pH adjusted to 7.2 with aqueous 1 M sodium hydroxide. Aliquots of 100 μL were taken at regular intervals and analysed by RP-HPLC. The eluent was acetonitrile/water (3:1) previously filtered through a Millipore, type HN 0.45 μm filter and degassed by ultra-sound for 30 min, at a flow rate of 0.8 mL/min for all compounds. The chromatograms were traced by detecting UV absorption at the wavelength of maximum absorption for each conjugate (retention time: 4a, 5.6; 4b, 4.5; 4c, 5.3; 4d, 7.8; 9a, 8.3; 9b, 7.7; 9c, 8.4 min). With methanol, potassium chloride, sodium chloride, calcium chloride, sodium hydroxide, magnesium chloride, N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid in water, pH= 7.2, Photolysis, Quantum yield, Kinetics, Wavelength Fonseca, Andrea S.C.; Goncalves, M. Sameiro T.; Costa, Susana P.G.; Tetrahedron; vol. 68; nb. 38; (2012); p. 8024 - 8032 View in Reaxys

O O O

HO O

Rx-ID: 33894129 View in Reaxys 155/824 Yield

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O N O

O O O

O N O HO O

Rx-ID: 33894134 View in Reaxys 156/824 Yield

O O O

O O

HO O

O O

Rx-ID: 33894135 View in Reaxys 157/824 Yield

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With methanol, potassium chloride, sodium chloride, calcium chloride, sodium hydroxide, magnesium chloride, N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid in water, pH= 7.2, Photolysis, Quantum yield, Kinetics, Wavelength Fonseca, Andrea S.C.; Goncalves, M. Sameiro T.; Costa, Susana P.G.; Tetrahedron; vol. 68; nb. 38; (2012); p. 8024 - 8032 View in Reaxys

O O O

O O

HO O

O O

Rx-ID: 33894137 View in Reaxys 158/824 Yield

O O O

HO O

Rx-ID: 33894139 View in Reaxys 159/824 Yield

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analysed by RP-HPLC. The eluent was acetonitrile/water (3:1) previously filtered through a Millipore, type HN 0.45 μm filter and degassed by ultra-sound for 30 min, at a flow rate of 0.8 mL/min for all compounds. The chromatograms were traced by detecting UV absorption at the wavelength of maximum absorption for each conjugate (retention time: 4a, 5.6; 4b, 4.5; 4c, 5.3; 4d, 7.8; 9a, 8.3; 9b, 7.7; 9c, 8.4 min). With methanol, potassium chloride, sodium chloride, calcium chloride, sodium hydroxide, magnesium chloride, N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid in water, pH= 7.2, Photolysis, Quantum yield, Kinetics Fonseca, Andrea S.C.; Goncalves, M. Sameiro T.; Costa, Susana P.G.; Tetrahedron; vol. 68; nb. 38; (2012); p. 8024 - 8032 View in Reaxys

O O O

HO O

Rx-ID: 33894140 View in Reaxys 160/824 Yield

HO O

O O

Rx-ID: 33894199 View in Reaxys 161/824 Yield

Conditions & References Reaction Steps: 2 1.1: sulfuric acid / water / 120 h / 20 °C 1.2: 24 h / 20 °C

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2.1: methanol; potassium chloride; sodium chloride; calcium chloride; sodium hydroxide; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid / water / pH 7.2 / Photolysis With methanol, sulfuric acid, potassium chloride, sodium chloride, calcium chloride, sodium hydroxide, magnesium chloride, N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid in water, 1.1: Pechmann condensation Fonseca, Andrea S.C.; Goncalves, M. Sameiro T.; Costa, Susana P.G.; Tetrahedron; vol. 68; nb. 38; (2012); p. 8024 - 8032 View in Reaxys O HO

Rx-ID: 33919382 View in Reaxys 162/824 Yield

Conditions & References With 2-hydroperoxypropane in acetonitrile, Time= 36h, T= 70 °C Biradar, Ankush V.; Asefa, Tewodros; Applied Catalysis A: General; vol. 435-436; (2012); p. 19 - 26 View in Reaxys O

O Mg

N Br

O O OH

N H

Rx-ID: 33929820 View in Reaxys 163/824 Yield

Conditions & References

41 %Spectr., 14 %Spectr., 17 %Spectr.

in diethyl ether, Time= 1h, T= 20 °C Boukattaya, Fatma; Stanovych, Andrii; Setzer, Paul; Abid, Souhir; Ammar, Houcine; Pearson-Long, Morwenna S. M.; Bertus, Philippe; Chemical Communications; vol. 48; nb. 69; (2012); p. 8655 - 8657 View in Reaxys O

O S

Rx-ID: 34054893 View in Reaxys 164/824 Yield 74 %

Conditions & References With bis(triphenylphosphine)nickel(II) diiodide, tricyclohexylphosphine in tetrahydrofuran, T= 80 °C , Inert atmosphere, Kumada Cross-Coupling Wu, Ji-Cheng; Gong, Lu-Bing; Xia, Yuanzhi; Song, Ren-Jie; Xie, Ye-Xiang; Li, Jin-Heng; Angewandte Chemie - International Edition; vol. 51; nb. 39; (2012); p. 9909 - 9913 View in Reaxys

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O O

Mg Br

Rx-ID: 4352830 View in Reaxys 165/824 Yield

Conditions & References

70 %

With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride, sodium iodide in tetrahydrofuran, T= 0 °C Malanga, Corrado; Aronica, Laura A.; Lardicci, Luciano; Tetrahedron Letters; vol. 36; nb. 50; (1995); p. 9185 - 9188 View in Reaxys

54 %

Stage 1: With 1-methyl-pyrrolidin-2-one in toluene, Time= 0.5h, T= 0 °C Stage 2: in tetrahydrofuran, toluene, Time= 4.25h, T= -10 - 0 °C , chemoselective reaction Gowda, Maravanhalli Sidde; Pande, Sushanth Sudhir; Ramakrishna, Ramesha Andagar; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 9; nb. 15; (2011); p. 5365 - 5368 View in Reaxys Stage 1: With triethylamine in dichloromethane, Time= 16h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 1h, T= 0 °C Stage 3: With hydrogenchloride in tetrahydrofuran, Time= 0.25h, T= 0 °C , Further stages. Hansen, Anne-Lene L.; Murray, Anthony; Tanner, David; Organic and Biomolecular Chemistry; vol. 4; nb. 24; (2006); p. 4497 - 4505 View in Reaxys O HO

HO O

Rx-ID: 4886109 View in Reaxys 166/824 Yield

Conditions & References

13 %, 85 %

With potassium superoxide, 2-Nitrobenzenesulfonyl chloride in acetonitrile, Time= 5h, T= -20 °C Kim II, Yong; Kim, Yong Hae; Tetrahedron Letters; vol. 39; nb. 7; (1998); p. 639 - 642 View in Reaxys

15 %Chromat., 79 %

With dihydrogen peroxide in water, acetonitrile, Time= 10h, T= 25 °C , UV-irradiation Farhadi, Saeid; Zabardasti, Abedien; Rahmati, Mohammad Hosien; Journal of Chemical Research; vol. 35; nb. 3; (2011); p. 157 - 160 View in Reaxys O

O O

Rx-ID: 30068417 View in Reaxys 167/824 Yield

Conditions & References

10 %Spectr. With RuCl(CO2)(η5C5Ph5), potassium tert-butylate, sodium carbonate in tetrahydrofuran, toluene, Time= 36h, T= 60 °C , Resolution of racemate, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Engstroem, Karin; Vallin, Michaela; Syren, Per-Olof; Hult, Karl; Baeckvall, Jan-E.; Organic and Biomolecular Chemistry; vol. 9; nb. 1; (2011); p. 81 - 82 View in Reaxys

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OH HO

HO O

Rx-ID: 30282725 View in Reaxys 168/824 Yield 9 %Spectr., 23 %Spectr., 63 %Spectr.

Conditions & References 4 :In a vacuum-sealed tube and a final reaction volume of 0.50 ml in toluene, 1- phenylpropan-l,3-diol (0.225 mmol), was heated to 175 0C with carbonyl- Ws(trifluoroacetato)Ms(triphenylphosphino)rathenium(II) (0.0112 mmol) and (9,9- dimethylxanthene-4,5-diyl)Ms(diphenylphosphine) (0.0112 mmol). After 17 h, full consumption of the starting material yielded propiophenone (0.142 mmol, 63percent), 1-phenylpropan-l-ol (0.0203 mmol, 9percent), and acetophenone (0.0518 mmol, 23percent) as determined by 1H NMR integration relative to an external capillary standard. Product identification was further confirmed by GC- MS for propiophenone (134 m/z), 1-phenylpropan-l-ol (136 m/z), and acetophenone (120 m/z). With carbonyl-bis(trifluoroacetato)bis(triphenylphosphino)ruthenium(II), 4,5-bis(diphenylphosphino)-9 ,9-dimethylxanthene in toluene, Time= 17h, T= 175 °C , vacuum-sealed tube, Product distribution / selectivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERGMAN, Robert; ELLMAN, Jonathan; NICHOLS, Jason; BISHOP, Lee; VOLKMAN, Jerome; TOSTE, Dean; SON, Sunghee; HARTWIG, John; SERGEEV, Alexey; WO2011/3029; (2011); (A2) English View in Reaxys O

HO O

Rx-ID: 30282726 View in Reaxys 169/824 Yield

Conditions & References

20 3 :In a vacuum-sealed tube and a final reaction volume of 0.50 ml in toluene, 3- hydroxy-1-phenylpropan-l-one (0.225 mmol) %Spectr., was heated to 175 0C with carbonyl- b/i'(trifluoroacetato)b/5'(triphenylphosphino)ruthenium(II) (0.0112 mmol) and (9,9- dime51 %Spectr. thylxanthene-4,5-diyl)Ms(diphenylphosphine) 0.0112 mmol). After 2.5 h, full consumption of the starting material yielded propiophenone (0.115 mmol, 51percent) and acetophenone (0.0450 mmol, 20percent) as determined by 1H NMR integration relative to an external capillary standard.416272008740 O-Q Product identification was further confirmed by GC-MS for propiophenone (134 m/z) and acetophenone (120 m/z). With carbonyl-bis(trifluoroacetato)bis(triphenylphosphino)ruthenium(II), 4,5-bis(diphenylphosphino)-9 ,9-dimethylxanthene in toluene, Time= 2.5h, T= 175 °C , vacuum-sealed tube, Product distribution / selectivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERGMAN, Robert; ELLMAN, Jonathan; NICHOLS, Jason; BISHOP, Lee; VOLKMAN, Jerome; TOSTE, Dean; SON, Sunghee; HARTWIG, John; SERGEEV, Alexey; WO2011/3029; (2011); (A2) English View in Reaxys

O O

Rx-ID: 30282727 View in Reaxys 170/824

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Yield

Conditions & References

13 %, 13 %, 10 :The decomposition of {P,G}-dimer (Example 7, X = OH) proceeds in high conversion (91percent) and reasonable yield of 21 % C-terminus products (78percent). However, the cleavage efficiency is low (33percent). The reaction was selective for the retroaldol manifold over elimination (RA/E = 12:1). However, the retroaldol selectivity was in favor of the η-retroaldol (ηη/η = 1:2.4) that does not lead directly to dimmer cleavage and inhibits the C-O bond cleavage process. Thus, phenoxyacetophenone derivatives build-up contributing to the C-terminus product yield, but cannot be converted forward resulting in poor cleavage efficiency. With [RuH2(CO)(PPh3)3], 4,5-bis(diphenylphosphino)-9 ,9-dimethylxanthene in toluene, Time= 4h, T= 150 °C , Inert atmosphere, Product distribution / selectivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERGMAN, Robert; ELLMAN, Jonathan; NICHOLS, Jason; BISHOP, Lee; VOLKMAN, Jerome; TOSTE, Dean; SON, Sunghee; HARTWIG, John; SERGEEV, Alexey; WO2011/3029; (2011); (A2) English View in Reaxys OH

O H

Rx-ID: 30282740 View in Reaxys 171/824 Yield 5 %Spectr., 20 %Spectr., 5 %Spectr., 5 %Spectr., 20 %Spectr., 10 %Spectr.

Conditions & References 5 :In a vacuum- sealed tube (0.1-0.2 torr) and a final reaction volume of 0.50 ml in toluene, 2-phenoxy-l-phenylpropan-l,3-diol (0.225 mmol), was heated to 175 0C with carbonylhydridotrifluoroacetato-b/i'(triphenylphosphino)ruthenium(II) (0.0112 mmol) and (9,9- dimethylxanthene-4,5-diyl)Ms(diphenylphosphine) (0.0112 mmol). After 6 h, 90percent consumption of the starting material yielded propiophenone (0.0450 mmol, 20percent), acetophenone (0.0112 mmol, 5percent), 2-phenoxyacetophenone (0.0112 mmol, 5percent), benzaldehyde (0.0112 mmol, 5percent), benzyl alcohol (0.0224 mmol, 10percent), and 2-phenoxy-lphenethanol (0.0450 mmol, 20percent) as determined by 1H NMR integration relative to an external capillary standard. With carbonyl-bis(trifluoroacetato)bis(triphenylphosphino)ruthenium(II), 4,5-bis(diphenylphosphino)-9 ,9-dimethylxanthene in toluene, Time= 6h, T= 175 °C , vacuum-sealed tube, Product distribution / selectivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERGMAN, Robert; ELLMAN, Jonathan; NICHOLS, Jason; BISHOP, Lee; VOLKMAN, Jerome; TOSTE, Dean; SON, Sunghee; HARTWIG, John; SERGEEV, Alexey; WO2011/3029; (2011); (A2) English View in Reaxys O O

O O

Rx-ID: 30282743 View in Reaxys 172/824 Yield 89 %, 40 %

Conditions & References 6 :Without being bound by any theory, an η,η-unsaturated intermediate most likely leads to C-O bond cleavage to yield propiophenone. 2-phenoxyphenylpropanol does not react under the reaction conditions to yield C-O bond cleavage products. However, the η,η-unsaturated ketone reacts faster than phenoxyacetophenone to yield propiophenone at lower temperatures. Thus, when starting

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with the η-[O]-4'-glycerolaryl ethers, selectivity for producing the η,η- unsaturated ketone may result in higher yields of propiophenone. With hydrogen, [RuH2(CO)(PPh3)3], 4,5-bis(diphenylphosphino)-9 ,9-dimethylxanthene in toluene, Time= 25.5h, T= 95 °C , Inert atmosphere, Product distribution / selectivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERGMAN, Robert; ELLMAN, Jonathan; NICHOLS, Jason; BISHOP, Lee; VOLKMAN, Jerome; TOSTE, Dean; SON, Sunghee; HARTWIG, John; SERGEEV, Alexey; WO2011/3029; (2011); (A2) English View in Reaxys

H O

O OH

O O

Rx-ID: 30282744 View in Reaxys 173/824 Yield

Conditions & References 7 :Measures of selectivity were defined based on relative quantities of the C-terminus products from the decomposition of η[O]-4'-glycerolaryl ethers. The distinction between C- terminus and O-terminus is only useful for model systems. In the actual lignin biopolymer, the O-terminus would exist on the same molecule as the C-terminus and no distinction would be necessary. In the subsequent data, all parameters are calculated from the product distribution (A-F). The selectivity parameter of interest for C-O bond cleavage processes is the retro-aldol vs. elimination selectivity (RA:E).416272008740 94 total percentTemp (C) percent conv. percent cleav. RA/E η/η C-O/C=O yield135 94 74 33 15:1 1:1.9 1:4.6 150 80 81 38 15:1 1:1.8 1:4.6 180 96 80 34 22:1 1:1.5 1:4.5[00255] A baseline reactivity profile for 2-(2-methoxyphenoxy)-l-phenylpropane-l,3-diol, abbreviated as {P,G}-dimer (The {X,Y} nomenclature is defined: X = C-terminus aryl substituent, Y = O-terminus aryl substituent on the 2-arylether-l,3propanediol backbone. P = phenyl, C = coumaryl, G = guaiacyl, S = syringyl), using conditions derived for thephenoxyphenethanols is shown above. Without additives, the disproportionation of the {P-G}- dimer favors retro-aldol processes (RA/E = 15:1). The retro-aldol favors cleaving the hydroxymethyl group (ηη/η = 1:1.9), and the hydrogen in the system goes primarily to reduce carbonyls (C-O/C=O = 1:4.6). These selectivities are relatively constant over a broad temperature range (135 - 180). Without being bound by any theory, based on these selectivities we can make some qualitative assessment of reaction limiters. For example, the reaction shown above is selective for retroaldol processes that a) reduce the amount of elimination to form the requisite η,η-unsaturated ketone, and b) yields aldehydes that are better hydrogen acceptors. Thus, C-O bond cleavage is suppressed. With [RuH2(CO)(PPh3)3], 4,5-bis(diphenylphosphino)-9 ,9-dimethylxanthene in (2)H8-toluene, Time= 4h, T= 150 °C , Inert atmosphere, Product distribution / selectivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERGMAN, Robert; ELLMAN, Jonathan; NICHOLS, Jason; BISHOP, Lee; VOLKMAN, Jerome; TOSTE, Dean; SON, Sunghee; HARTWIG, John; SERGEEV, Alexey; WO2011/3029; (2011); (A2) English View in Reaxys

O O

O H

O O

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O O

Rx-ID: 30282746 View in Reaxys 174/824 Yield

Conditions & References 9 :The structure of lignin in Miscanthus giganteus has been analyzed, and the native lignin is composed of 93percent η- [O] -4' glycerolarylether linkages. However, 43percent of those linkages are acylated at the hydroxymethyl (η) position with acetate, or pcoumaric acid. Based on the RA/E selectivity trends, the η-acylated glycerolarylethers may favor elimination, and therefore C-O bond cleavage.[00261] A non-natural acylated lignin model, 3-hydroxy-2-(2-methoxyphenoxy)-3- phenylpropyl 2,2-dimethylpropanoate (η-OPiv-{P,G}-dimer) was reacted with the ruthenium catalyst. Decomposition of the η-OPiv-{P,G}-dimer produces mostly propiophenone. The RA/E selectivity decreases from 12:1 in favor of retroaldol for X = OH to 1:2.1 in favor of elimination. Changing X to OAc yields a natural model of a lignin linkage (η-OAc-{P,G}-dimer).Decomposition of η-OAc-{P,G}-dimer produces propiophenone and acetophenone as the major products, resulting in a higher overall cleavage when compared to the ηOPiv-{P,G}-dimer. An increase in retroaldol activity (RA/E = 1:1.5) that was selective for the cleavage of η-416272008740 97 hydroxymethyl units (ηη:η = 1:1.5) and selectively used liberated H2 for C-O (C-O/C=O = 1.2:1). With [RuH2(CO)(PPh3)3], 4,5-bis(diphenylphosphino)-9 ,9-dimethylxanthene in (2)H8-toluene, Time= 20h, T= 150 °C , Inert atmosphere, Product distribution / selectivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERGMAN, Robert; ELLMAN, Jonathan; NICHOLS, Jason; BISHOP, Lee; VOLKMAN, Jerome; TOSTE, Dean; SON, Sunghee; HARTWIG, John; SERGEEV, Alexey; WO2011/3029; (2011); (A2) English View in Reaxys

O O

Rx-ID: 30282748 View in Reaxys 175/824 Yield

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Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERGMAN, Robert; ELLMAN, Jonathan; NICHOLS, Jason; BISHOP, Lee; VOLKMAN, Jerome; TOSTE, Dean; SON, Sunghee; HARTWIG, John; SERGEEV, Alexey; WO2011/3029; (2011); (A2) English View in Reaxys O O

Rx-ID: 30458552 View in Reaxys 176/824 Yield

Conditions & References

31 %, 34 %Spectr.

4.3. Reverse reaction In a two-necked flask equipped with a reflux condenser were placed RhH(PPh3)4 (4 mol percent, 11.5 mg), 1,2-bis(diphenylphosphino)ethane (8 mol percent, 8.0 mg), 6 (0.25 mmol, 45.1 mg), 2 (0.25 mmol, 49.1 mg), and dimethyl disulfide (12 mol percent, 2.7 μL) in THF (0.25 mL) under an argon atmosphere, and the solution was heated at 90 °C for 3 h. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel giving 1 (18.9 mg, 31percent) as well as the recovery of 2 (33.4 mg, 68percent), and 6 (25.6 mg, 57percent). The yield of 5 (34percent) was determined by 1H NMR using 1,1,2-tricholoroethane as an internal standard. With hydridotetakis(triphenylphosphine)rhodium(I), Dimethyldisulphide, 1,2-bis-(diphenylphosphino)ethane in tetrahydrofuran, Time= 3h, T= 90 °C , Inert atmosphere Arisawa, Mieko; Toriyama, Fumihiko; Yamaguchi, Masahiko; Tetrahedron; vol. 67; nb. 12; (2011); p. 2305 - 2312 View in Reaxys

O S O

Rx-ID: 30703717 View in Reaxys 177/824 Yield

Conditions & References

85 %

With titanium(IV) iodide in propiononitrile, Time= 16h, T= 20 °C , Inert atmosphere Hachiya, Iwao; Inagaki, Takao; Ishihara, Yasuhisa; Shimizu, Makoto; Bulletin of the Chemical Society of Japan; vol. 84; nb. 4; (2011); p. 419 - 421 View in Reaxys O

O S

Rx-ID: 30703719 View in Reaxys 178/824 Yield 80 %

Conditions & References With titanium(IV) iodide in propiononitrile, Time= 13h, T= 20 °C , Inert atmosphere

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Hachiya, Iwao; Inagaki, Takao; Ishihara, Yasuhisa; Shimizu, Makoto; Bulletin of the Chemical Society of Japan; vol. 84; nb. 4; (2011); p. 419 - 421 View in Reaxys O N

O N

S O

Rx-ID: 30707644 View in Reaxys 179/824 Yield

O N

S S

Rx-ID: 30707654 View in Reaxys 180/824 Yield 13 %

Conditions & References Typical Procedures for Methylthiolation Reaction. 2-Methylthio-1,3-benzothiazole 118,9 General procedure: In a two-necked flask equipped with a reflux condenser were placed RhH(PPh3)4 (4 molpercent, 11.5 mg), 1,2-bis(diphenylphosphino)ethane (8 molpercent, 8.0 mg), dimethyl disulfide (12 molpercent, 2.7 mL), 1,3-benzothiazole 5 (1.25 mmol, 137 mL), and (η-methylthio)isobutyrophenone 10 (0.25 mmol, 48.6 mg) in THF (0.25 mL) under an argon atmosphere, and the solution was heated at 90°C for 3 h. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel giving 11 (19.6 mg, 43percent) and isobutyrophenone 8 (14.7 mg, 40percent) with the recovery of 5 (141.1 mg, 83percent) and 10 (23.7 mg, 49percent). With hydridotetakis(triphenylphosphine)rhodium(I), Dimethyldisulphide, 1,2-bis-(diphenylphosphino)ethane in tetrahydrofuran, Time= 3h, T= 90 °C , Inert atmosphere Arisawa, Mieko; Toriyama, Fumihiko; Yamaguchi, Masahiko; Tetrahedron Letters; vol. 52; nb. 18; (2011); p. 2344 - 2347 View in Reaxys Typical Procedures for Methylthiolation Reaction. 2-Methylthio-1,3-benzothiazole 118,9 General procedure: In a two-necked flask equipped with a reflux condenser were placed RhH(PPh3)4 (4 molpercent, 11.5 mg), 1,2-bis(diphenylphosphino)ethane (8 molpercent, 8.0 mg), dimethyl disulfide (12 molpercent, 2.7 mL), 1,3-benzothiazole 5 (1.25 mmol, 137 mL), and (η-methylthio)isobutyrophenone 10 (0.25 mmol, 48.6 mg) in THF (0.25 mL) under an argon atmosphere, and the solution was heated at 90°C for 3 h. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel giving 11 (19.6 mg, 43percent) and isobutyrophenone 8 (14.7 mg, 40percent) with the recovery of 5 (141.1 mg, 83percent) and 10 (23.7 mg, 49percent). With hydridotetakis(triphenylphosphine)rhodium(I), Dimethyldisulphide, 1,2-bis-(diphenylphosphino)ethane in tetrahydrofuran, T= 90 °C , Inert atmosphere Arisawa, Mieko; Toriyama, Fumihiko; Yamaguchi, Masahiko; Tetrahedron Letters; vol. 52; nb. 18; (2011); p. 2344 - 2347 View in Reaxys

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O O

F F

B–

K+

Rx-ID: 30786418 View in Reaxys 181/824 Yield

Conditions & References

73 %

With dipotassium peroxodisulfate, palladium diacetate in water, dimethyl sulfoxide, Time= 3h, T= 20 °C Li, Mingzong; Wang, Cong; Ge, Haibo; Organic Letters; vol. 13; nb. 8; (2011); p. 2062 - 2064 View in Reaxys O

N O

Rx-ID: 30913573 View in Reaxys 182/824 Yield

Conditions & References Reaction Steps: 2 1: sodium hydrogencarbonate / chloroform 2: OPR3 isoenzyme of 12-oxophytodienoate reductase from Lycopersicon esculentum; NADH / 24 h / 30 °C / pH 7.5 / aq. buffer; Enzymatic reaction With OPR3 isoenzyme of 12-oxophytodienoate reductase from Lycopersicon esculentum, sodium hydrogencarbonate, NADH in chloroform Durchschein, Katharina; Fabian, Walter M. F.; MacHeroux, Peter; Zangger, Klaus; Trimmel, Gregor; Faber, Kurt; Organic and Biomolecular Chemistry; vol. 9; nb. 9; (2011); p. 3364 - 3369 View in Reaxys Reaction Steps: 2 1: sodium hydrogencarbonate / chloroform 2: xenobiotic reductase A from Pseudomonas putida; NADH / 24 h / 30 °C / pH 7.5 / aq. buffer; Enzymatic reaction With xenobiotic reductase A from Pseudomonas putida, sodium hydrogencarbonate, NADH in chloroform Durchschein, Katharina; Fabian, Walter M. F.; MacHeroux, Peter; Zangger, Klaus; Trimmel, Gregor; Faber, Kurt; Organic and Biomolecular Chemistry; vol. 9; nb. 9; (2011); p. 3364 - 3369 View in Reaxys O

O N O

Rx-ID: 30913575 View in Reaxys 183/824 Yield

Conditions & References With xenobiotic reductase A from Pseudomonas putida, NADH, Time= 24h, T= 30 °C , pH= 7.5, aq. buffer, Enzymatic reaction Durchschein, Katharina; Fabian, Walter M. F.; MacHeroux, Peter; Zangger, Klaus; Trimmel, Gregor; Faber, Kurt; Organic and Biomolecular Chemistry; vol. 9; nb. 9; (2011); p. 3364 - 3369 View in Reaxys

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O N

Rx-ID: 30913578 View in Reaxys 184/824 Yield

Conditions & References With OPR3 isoenzyme of 12-oxophytodienoate reductase from Lycopersicon esculentum, NADH, Time= 24h, T= 30 °C , pH= 7.5, aq. buffer, Enzymatic reaction Durchschein, Katharina; Fabian, Walter M. F.; MacHeroux, Peter; Zangger, Klaus; Trimmel, Gregor; Faber, Kurt; Organic and Biomolecular Chemistry; vol. 9; nb. 9; (2011); p. 3364 - 3369 View in Reaxys O O

Rx-ID: 31330960 View in Reaxys 185/824 Yield 67 %, 8 %Spectr.

Conditions & References With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], Selectfluor in tetrahydrofuran, water, Time= 15h, T= 30 °C , Inert atmosphere, regiospecific reaction Ahlsten, Nanna; Martin-Matute, Belen; Chemical Communications; vol. 47; nb. 29; (2011); p. 8331 - 8333 View in Reaxys

67 %, 8 %Spectr.

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], selectfluor in tetrahydrofuran, water, Time= 15h, T= 25 °C , regiospecific reaction Ahlsten, Nanna; Bartoszewicz, Agnieszka; Agrawal, Santosh; Martin-Matute, Belen; Synthesis; nb. 16; (2011); p. 2600 2608; Art.No: C57411SS View in Reaxys O O

Rx-ID: 31472798 View in Reaxys 186/824 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 0 - 20 °C 2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; selectfluor / tetrahydrofuran; water / 15 h / 25 °C With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], selectfluor in tetrahydrofuran, water Ahlsten, Nanna; Bartoszewicz, Agnieszka; Agrawal, Santosh; Martin-Matute, Belen; Synthesis; nb. 16; (2011); p. 2600 2608; Art.No: C57411SS View in Reaxys O H

Mg Br

Rx-ID: 32044622 View in Reaxys 187/824

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Yield

Conditions & References

11 %, 25 %, Stage 1: With zinc(II) chloride in tetrahydrofuran, Time= 1h, T= 0 - 20 °C 25 % Stage 2: in tetrahydrofuran, Time= 8h, T= 0 °C Jagtap; Joshi; Tetrahedron Letters; vol. 52; nb. 48; (2011); p. 6501 - 6503 View in Reaxys O

Br N

Rx-ID: 33056587 View in Reaxys 188/824 Yield

Conditions & References Stage 1: With iodine, magnesium in diethyl ether, Inert atmosphere Stage 2: in diethyl ether, Time= 6h, Reflux, Grignard reaction Stage 3: With sulfuric acid, water in diethyl ether, Heating Lagoja, Irene; Pannecouque, Christophe; Griffioen, Gerard; Wera, Stefaan; Rojasdelaparra, Veronica Maria; Van Aerschot, Arthur; European Journal of Pharmaceutical Sciences; vol. 43; nb. 5; (2011); p. 386 - 392 View in Reaxys

O I (v2)

I Zn

(v2)

S O

Rx-ID: 10512278 View in Reaxys 189/824 Yield 56 %, 43 %

Conditions & References Stage 1: in tetrahydrofuran, Time= 2h, T= 25 °C Stage 2: With ammonium chloride Nomura, Kenichi; Matsubara, Seijiro; Chemistry Letters; vol. 36; nb. 1; (2007); p. 164 - 165 View in Reaxys

56 %, 43 %

Stage 1: in tetrahydrofuran, Time= 2h, T= 25 °C Stage 2: With water, ammonium chloride in tetrahydrofuran Nomura, Kenichi; Matsubara, Seijiro; Chemistry - An Asian Journal; vol. 5; nb. 1; (2010); p. 147 - 152 View in Reaxys

OH HO OH OH

Rx-ID: 28765892 View in Reaxys 190/824 Yield 57 %, 30 %

Conditions & References Stage 1: With tert.-butyl lithium in tetrahydrofuran, pentane, Time= 0.166667h, T= 0 °C Stage 2: With lithium tri-tert-butylzincate in tetrahydrofuran, pentane, T= 0 - 65 °C Nomura, Kenichi; Matsubara, Seijiro; Chemical Communications; nb. 16; (2009); p. 2212 - 2213 View in Reaxys

57 %, 30 %

Stage 1: With tert.-butyl lithium in tetrahydrofuran, pentane, Time= 0.166667h, T= 0 °C Stage 2: With t-Bu3ZnLi in tetrahydrofuran, pentane, Time= 1h, T= 0 - 47 °C , Reflux

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Nomura, Kenichi; Matsubara, Seijiro; Chemistry - A European Journal; vol. 16; nb. 2; (2010); p. 703 - 708 View in Reaxys O O

I (v2)

(v2)

Rx-ID: 29193645 View in Reaxys 191/824 Yield

Conditions & References

17 Stage 1: in tetrahydrofuran, Time= 15h, T= 25 °C %Spectr., Stage 2: in tetrahydrofuran, Acidic aq. solution 21 %Spectr. Nomura, Kenichi; Matsubara, Seijiro; Chemistry - An Asian Journal; vol. 5; nb. 1; (2010); p. 147 - 152 View in Reaxys OH

Rx-ID: 29520751 View in Reaxys 192/824 Yield

Conditions & References Stage 1: With tert.-butyl lithium in tetrahydrofuran, pentane, Time= 0.166667h, T= 0 °C Stage 2: With t-Bu3ZnLi in tetrahydrofuran, pentane, T= 0 - 60 °C , Reflux Nomura, Kenichi; Matsubara, Seijiro; Chemistry - A European Journal; vol. 16; nb. 2; (2010); p. 703 - 708 View in Reaxys

O O

Rx-ID: 29600988 View in Reaxys 193/824 Yield

Conditions & References With toluene-4-sulfonic acid, T= 20 °C , p= 5.25053Torr Sonawane, Manoj R.; Cisaova, Ivana; Lyapkalo, Ilya M.; Chemical Communications; vol. 46; nb. 15; (2010); p. 2656 - 2658 View in Reaxys

Rx-ID: 29626657 View in Reaxys 194/824

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Yield

Conditions & References

64 %, 36 %

With [Ru(η(5)-C5,η-P-Cp(P))(CH3CN)2]PF6 in tetrahydrofuran-d8, Time= 1.91667h, T= 60 °C , Inert atmosphere Batuecas, Maria; Esteruelas, Miguel A.; Garcia-Yebra, Cristina; Onate, Enrique; Organometallics; vol. 29; nb. 9; (2010); p. 2166 - 2175 View in Reaxys O Cl

HO Cl

Rx-ID: 29676960 View in Reaxys 195/824 Yield

Conditions & References

28 %, 12 Stage 1: With magnesium in tetrahydrofuran, N,N-dimethyl acetamide %Chromat., Stage 2: With dihydrogen peroxide, sodium hydroxide in water 15 %ChroCondon, Sylvie; Nedelec, Jean-Yves; Journal of Organometallic Chemistry; vol. 695; nb. 1; (2010); p. 32 - 35 mat. View in Reaxys

O O Si Br

Rx-ID: 29696411 View in Reaxys 196/824 Yield 70 %

Conditions & References Stage 1: With tri-tert-butyl phosphine, tetrabutylammonium triphenyldifluorosilicate, bis(dibenzylideneacetone)-palladium(0) in toluene, T= 95 °C , Inert atmosphere Stage 2: With silica gel in toluene Guo, Yong; Tao, Guo-Hong; Blumenfeld, Alex; Shreeve, Jean'ne M.; Organometallics; vol. 29; nb. 7; (2010); p. 1818 - 1823 View in Reaxys

O O Si Br

Rx-ID: 29696424 View in Reaxys 197/824 Yield 47 %

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O O Si O

Rx-ID: 29696431 View in Reaxys 198/824 Yield

79 %

Guo, Yong; Tao, Guo-Hong; Blumenfeld, Alex; Shreeve, Jean'ne M.; Organometallics; vol. 29; nb. 7; (2010); p. 1818 - 1823 View in Reaxys

O Br

O O O

Rx-ID: 29696432 View in Reaxys 199/824 Yield

40 %

Guo, Yong; Tao, Guo-Hong; Blumenfeld, Alex; Shreeve, Jean'ne M.; Organometallics; vol. 29; nb. 7; (2010); p. 1818 - 1823 View in Reaxys

O O

N O

Rx-ID: 29764699 View in Reaxys 200/824 Yield

Conditions & References With Aspergillus oryzae MIM, Time= 6h, T= 30 °C , pH= 7, aq. phosphate buffer, Resolution of racemate, optical yield given as percent ee, enantioselective reaction Paravidino, Monica; Holt, Jarle; Romano, Diego; Singh, Neetu; Arends, Isabel W.C.E.; Minnaard, Adriaan J.; Orru, Romano V.A.; Molinari, Francesco; Hanefeld, Ulf; Journal of Molecular Catalysis B: Enzymatic; vol. 63; nb. 1-2; (2010); p. 87 92 View in Reaxys

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O O

Rx-ID: 29804256 View in Reaxys 201/824 Yield

Conditions & References

61 %, 5 %, 21 %

With platinum(II) chloride, Time= 20h, T= 70 °C , Inert atmosphere, neat (no solvent) Munoz, Maria Paz; De La Torre, Maria C.; Sierra, Miguel A.; Advanced Synthesis and Catalysis; vol. 352; nb. 13; (2010); p. 2189 - 2194 View in Reaxys O HO

B HO

Rx-ID: 29902162 View in Reaxys 202/824 Yield

Conditions & References With tetrakis(triphenylphosphine) palladium(0), water, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline in N,N-dimethyl-formamide, Time= 15h, T= 60 °C , Inert atmosphere

79 %

Kwon, Young Bum; Choi, Bo Ram; Lee, Seung Hwan; Seo, Jin-Soo; Yoon, Cheol Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 9; (2010); p. 2672 - 2674 View in Reaxys

O O

NH 2

OH O

Rx-ID: 30043550 View in Reaxys 203/824 Yield

Conditions & References With (S)-specific η-transaminase from Paracoccus denitrificans in water, pH= 7, aq. phosphate buffer, Enzymatic reaction Park, Eulsoo; Kim, Minji; Shin, Jong-Shik; Advanced Synthesis and Catalysis; vol. 352; nb. 18; (2010); p. 3391 - 3398 View in Reaxys

O OH

Rx-ID: 30364371 View in Reaxys 204/824 Yield

Conditions & References With [RuCl2(η6-p-cymene)((R)-PhOP(binaphthoxy))], potassium tert-butylate in tetrahydrofuran, Time= 0.25h, T= 45 °C , Inert atmosphere, Resolution of racemate, optical yield given as percent ee, enantioselective reaction Fernandez-Zumel, Mariano A.; Lastra-Barreira, Beatriz; Scheele, Marcus; Diez, Josefina; Crochet, Pascale; Gimeno, Jose; Dalton Transactions; vol. 39; nb. 33; (2010); p. 7780 - 7785 View in Reaxys

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O O HO

Rx-ID: 30669244 View in Reaxys 205/824 Yield

Conditions & References

54 %Chromat., 41 %Chromat.

With ammonium cerium (IV) nitrate, lithium bromide in water, acetonitrile, Time= 7h, T= 65 °C Nikishin; Sokova; Kapustina; Russian Chemical Bulletin; vol. 59; nb. 2; (2010); p. 391 - 395 View in Reaxys

N HO

Rx-ID: 30683512 View in Reaxys 206/824 Yield

Conditions & References Reaction Steps: 2 1: sodium iodide / diethyl ether / 48 h / Reflux 2: [N-[(1R,2R)-2-(amino-ηN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-ηN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium; formic acid; triethylamine / ethyl acetate / 168 h / 20 °C / Inert atmosphere With formic acid, [N-[(1R,2R)-2-(amino-ηN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-ηN]chloro[(1,2, 3,4,5,6-η)-1methyl-4-(1-methylethyl)benzene]-ruthenium, triethylamine, sodium iodide in diethyl ether, ethyl acetate Kosmalski, Tomasz; Acta Poloniae Pharmaceutica - Drug Research; vol. 67; nb. 6; (2010); p. 717 - 721 View in Reaxys

N HO

Rx-ID: 30683517 View in Reaxys 207/824 Yield

Conditions & References

16 %, 71 %

With formic acid, [N-[(1R,2R)-2-(amino-ηN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-ηN]chloro[(1,2, 3,4,5,6-η)-1methyl-4-(1-methylethyl)benzene]-ruthenium, triethylamine in ethyl acetate, Time= 168h, T= 20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Kosmalski, Tomasz; Acta Poloniae Pharmaceutica - Drug Research; vol. 67; nb. 6; (2010); p. 717 - 721 View in Reaxys O

N N

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O O H N

N H

Rx-ID: 28409861 View in Reaxys 208/824 Yield

Conditions & References

92 %

With zinc dibromide in toluene, Time= 1h, Reflux Cao, Hai Thuong; Gree, Rene; Tetrahedron Letters; vol. 50; nb. 13; (2009); p. 1493 - 1494 View in Reaxys O HO

N N

O O H N

N H

Rx-ID: 28409862 View in Reaxys 209/824 Yield

Conditions & References

96 %, 96 %

With zinc dibromide in toluene, Time= 0.5h, Reflux Cao, Hai Thuong; Gree, Rene; Tetrahedron Letters; vol. 50; nb. 13; (2009); p. 1493 - 1494 View in Reaxys

O H 2N

NH 2

Rx-ID: 28538750 View in Reaxys 210/824 Yield 50 %Chromat.

Conditions & References With transaminase ATA-117, pyridoxal 5'-phosphate, sodium pyruvate, Time= 24h, T= 30 °C , pH= 7.0, aq. phosphate buffer, Resolution of racemate, Enzymatic reaction, optical yield given as percent ee Koszelewski, Dominik; Clay, Dorina; Rozzell, David; Kroutil, Wolfgang; European Journal of Organic Chemistry; nb. 14; (2009); p. 2289 - 2292 View in Reaxys

82 %Chromat.

Stage 1: With transaminase ATA-117, pyridoxal 5'-phosphate, sodium pyruvate, Time= 24h, T= 30 °C , pH= 7.0, aq. phosphate buffer, Resolution of racemate, Enzymatic reaction Stage 2: With L-alanin, transaminase ATA-113, Time= 24h, T= 30 °C , aq. phosphate buffer, Enzymatic reaction, optical yield given as percent ee Koszelewski, Dominik; Clay, Dorina; Rozzell, David; Kroutil, Wolfgang; European Journal of Organic Chemistry; nb. 14; (2009); p. 2289 - 2292 View in Reaxys

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Rx-ID: 28565219 View in Reaxys 211/824 Yield

Conditions & References With iodine, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water, Time= 4h, T= 20 °C Moorthy, Jarugu Narasimha; Senapati, Kalyan; Singhal, Nidhi; Tetrahedron Letters; vol. 50; nb. 21; (2009); p. 2493 - 2496 View in Reaxys O

OH 2

O O 2H

2H 2H

Rx-ID: 28591128 View in Reaxys 212/824 Yield

Conditions & References

41 %Spectr., 8 %Spectr., 8 %Spectr., 33 %Spectr., 8 %Spectr.

With tris(triphenylphosphine)ruthenium(II) chloride, tri-tert-butyl phosphine, sodium formate in toluene, Time= 0.0833333h, T= 140 °C , Inert atmosphere Bartoszewicz, Agnieszka; Martin-Matute, Belen; Organic Letters; vol. 11; nb. 8; (2009); p. 1749 - 1752 View in Reaxys

HO O

Rx-ID: 28612235 View in Reaxys 213/824 Yield

Conditions & References

92 %

With 1H-imidazole, sodium periodate in water, acetonitrile, Time= 75h, T= 20 °C Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Mohammadpoor-baltork, Iraj; Sirjanian, Narges; Parand, Somayeh; Bioorganic and Medicinal Chemistry; vol. 17; nb. 9; (2009); p. 3394 - 3398 View in Reaxys

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Rx-ID: 28773769 View in Reaxys 214/824 Yield

Conditions & References

57 %, 20 %

Stage 1: With zinc(II) chloride, lithium tert-butoxide in tetrahydrofuran, Time= 2h, Reflux, Inert atmosphere Stage 2: in tetrahydrofuran, Time= 12h, T= 20 °C , Inert atmosphere, optical yield given as percent de, enantioselective reaction Coulbeck, Elliot; Eames, Jason; Tetrahedron Letters; vol. 50; nb. 31; (2009); p. 4449 - 4451 View in Reaxys

O O

Rx-ID: 28900235 View in Reaxys 215/824 Yield

Conditions & References With silver hexafluoroantimonate, silver(I) bifluoride, [RuCl2((1S,2S)-N,N'-bis[o-(diphenylphosphino)benzylidene]cyclohexane-1,2-diamine)] in 1,2-dichloro-ethane, Time= 24h, T= 60 °C , Darkness Althaus, Martin; Togni, Antonio; Mezzetti, Antonio; Journal of Fluorine Chemistry; vol. 130; nb. 8; (2009); p. 702 - 707 View in Reaxys O

H O

Rx-ID: 28961969 View in Reaxys 216/824 Yield

Conditions & References

35 %, 73 %

With 3-methylpyridin-2-ylamine, Wilkinson's catalyst, hexan-1-amine, 4-trifluoromethylbenzoic acid, water in toluene, Time= 24h, T= 150 °C Cha, Kyung-Mi; Jo, Eun-Ae; Jun, Chul-Ho; Synlett; nb. 18; (2009); p. 2939 - 2942 View in Reaxys O

O S

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O S

Rx-ID: 29032165 View in Reaxys 217/824 Yield

Conditions & References

9 %Spectr.

With chloro(1,5-cyclooctadiene)rhodium(I) dimer, potassium tert-butylate, triphenylphosphine in tetrahydrofuran, Time= 14h, T= 40 °C , Molecular sieve, optical yield given as percent de Ahlsten, Nanna; Martin-Matute, Belen; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2657 - 2666 View in Reaxys O

O S

Rx-ID: 29032166 View in Reaxys 218/824 Yield

Conditions & References

5 %Spectr.

F O F

Rx-ID: 29032167 View in Reaxys 219/824 Yield 4 %Spectr., 92 %

Conditions & References With chloro(1,5-cyclooctadiene)rhodium(I) dimer, potassium tert-butylate, triphenylphosphine in tetrahydrofuran, Time= 2h, T= 40 °C Ahlsten, Nanna; Martin-Matute, Belen; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2657 - 2666 View in Reaxys

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Cl O

Rx-ID: 29032168 View in Reaxys 220/824 Yield

Conditions & References

92 %, 4 %Spectr.

With chloro(1,5-cyclooctadiene)rhodium(I) dimer, potassium tert-butylate, triphenylphosphine in tetrahydrofuran, Time= 2h, T= 40 °C Ahlsten, Nanna; Martin-Matute, Belen; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2657 - 2666 View in Reaxys

O O

Rx-ID: 29032169 View in Reaxys 221/824 Yield

Conditions & References

15 %Spectr. With chloro(1,5-cyclooctadiene)rhodium(I) dimer, potassium tert-butylate, triphenylphosphine in tetrahydrofuran, Time= 1.25h, T= 40 °C , optical yield given as percent de Ahlsten, Nanna; Martin-Matute, Belen; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2657 - 2666 View in Reaxys HO

Rx-ID: 29032170 View in Reaxys 222/824 Yield 4 %Spectr.

Conditions & References With chloro(1,5-cyclooctadiene)rhodium(I) dimer, potassium tert-butylate, triphenylphosphine in tetrahydrofuran, Time= 2h, T= 40 °C , optical yield given as percent de Ahlsten, Nanna; Martin-Matute, Belen; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2657 - 2666 View in Reaxys

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N N

Rx-ID: 29117284 View in Reaxys 223/824 Yield 92 %

Conditions & References With selenium(IV) oxide, dihydrogen peroxide in methanol, T= 20 °C , pH= 7, aq. phosphate buffer Smith III, Amos B.; Liu, Zhuqing; Simov, Vladimir; Synlett; nb. 19; (2009); p. 3131 - 3134 View in Reaxys O O

H 2N

Rx-ID: 29118585 View in Reaxys 224/824 Yield

Conditions & References Stage 1: With 2-dicyclohexyl(2η,6η-dimethoxybiphenyl)phosphine gold(I)bis(trifluoromethanesulfonyl)imide in acetonitrile, Time= 24h, T= 80 °C Stage 2: With hydrogenchloride, water in acetonitrile, T= 20 °C , regioselective reaction Leyva, Antonio; Corma, Avelino; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2876 - 2886 View in Reaxys

O O

O F

N F

Rx-ID: 29150311 View in Reaxys 225/824 Yield

Conditions & References With water Fischer, Daniel F.; Barakat, Assem; Xin, Zhuo-Qun; Weiss, Matthias E.; Peters, Rene; Chemistry - A European Journal; vol. 15; nb. 35; (2009); p. 8722 - 8741 View in Reaxys

Rx-ID: 29255007 View in Reaxys 226/824

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Yield

Conditions & References

94 %, 6 %

With tris(dibenzylideneacetone)dipalladium(0) chloroform complex, methyl-malonic acid dimethylester, (R,R)-ANDEN-phenyl Trost ligand in 1,4-dioxane, Time= 0.5h, T= 20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Trost, Barry M.; Xu, Jiayi; Schmidt, Thomas; Journal of the American Chemical Society; vol. 131; nb. 51; (2009); p. 18343 18357 View in Reaxys

O O

Rx-ID: 29255008 View in Reaxys 227/824 Yield

Conditions & References

91 %, 83 %

With tris(dibenzylideneacetone)dipalladium(0) chloroform complex, (R,R)-ANDEN-phenyl Trost ligand in 1,4-dioxane, Time= 0.25h, T= 20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Trost, Barry M.; Xu, Jiayi; Schmidt, Thomas; Journal of the American Chemical Society; vol. 131; nb. 51; (2009); p. 18343 18357 View in Reaxys

O O

Rx-ID: 29255009 View in Reaxys 228/824 Yield

Conditions & References

90 %, 10 %

(v2)

Rx-ID: 614795 View in Reaxys 229/824 Yield 98 %

Conditions & References With ((t-Bu)2POH)2PdCl2 in 1-methyl-pyrrolidin-2-one, Time= 0.5h, T= 25 °C

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Xu, Hanhui; Ekoue-Kovi, Kekeli; Wolf, Christian; Journal of Organic Chemistry; vol. 73; nb. 19; (2008); p. 7638 - 7650 View in Reaxys With diethyl ether, Zersetzung des Reaktionsproduktes mit Wasser Kalle; Justus Liebigs Annalen der Chemie; vol. 119; (1861); p. 165 View in Reaxys Freund; Justus Liebigs Annalen der Chemie; vol. 118; (1861); p. 20 View in Reaxys With carbon monoxide, BrClMg, Pd Complex, palladium in tetrahydrofuran, Time= 16h, p= 22800Torr , Ambient temperature, Yield given Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 View in Reaxys With aluminium trichloride, 1.) CH2Cl2, 1 h, 2.) CH2Cl2, room temperature, 2 h, Yield given. Multistep reaction Arisawa, Mitsuhiro; Torisawa, Yasuhiro; Kawahara, Michiaki; Yamanaka, Masamichi; Nishida, Atsushi; Nakagawa, Masako; Journal of Organic Chemistry; vol. 62; nb. 13; (1997); p. 4327 - 4329 View in Reaxys Kalle; Justus Liebigs Annalen der Chemie; vol. 119; (1861); p. 165 View in Reaxys Freund; Justus Liebigs Annalen der Chemie; vol. 118; (1861); p. 20 View in Reaxys O

Rx-ID: 2087561 View in Reaxys 230/824 Yield 98 %

Conditions & References With manganese(IV) oxide, aluminium trichloride in acetonitrile, Time= 0.5h, Heating, Oxidation Firouzabadi, Habib; Etemadi, Shahrad; Karimi, Babak; Jarrahpour, Ali Asghar; Synthetic Communications; vol. 29; nb. 24; (1999); p. 4333 - 4339 View in Reaxys

95 %

With potassium permanganate, aluminium trichloride in acetone, Time= 0.0833333h, T= 20 °C , oxidative desilylation, Product distribution, Further Variations: Reagents, Solvents Firouzabadi, Habib; Etemadi, Shahrad; Karimi, Babak; Jarrahpour, Ali Asghar; Phosphorus, Sulfur and Silicon and Related Elements; vol. 152; (1999); p. 141 - 151 View in Reaxys

93 %

With chromium(VI) oxide, tert.-butylhydroperoxide, triphenylhydroxysilane in dichloromethane, Time= 15h, Ambient temperature Muzart; N'Ait Ajjou; Synthetic Communications; vol. 22; nb. 14; (1992); p. 1993 - 1996 View in Reaxys

93 %

With cetyltrimethylammonium peroxodisulphate in acetonitrile, Time= 0.283333h, Reflux Tajbakhsh, Mahmoud; Alinezhad, Heshmatollah; Urimi, Azade Geran; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 183; nb. 6; (2008); p. 1447 - 1454 View in Reaxys

92 %

With zinc dichromate(VI), T= 20 °C Firouzabadi, Habib; Hassani, Hassan; Gholizadeh, Mostafa; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 7; (2004); p. 1417 - 1422

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View in Reaxys 91 %

With potassium permanganate, tetrachlorosilane in acetonitrile, Time= 0.333333h, T= 20 °C Firouzabadi, Habib; Hazarkhani, Hassan; Hassani, Hassan; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 2; (2004); p. 403 - 409 View in Reaxys

91 %

With N-hydroxyphthalimide, oxygen, cobalt(II) benzoate in acetonitrile, Time= 1h, T= 20 °C Karimi, Babak; Rajabi, Jamshid; Organic Letters; vol. 6; nb. 17; (2004); p. 2841 - 2844 View in Reaxys

85 %

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, acetonitrile, Time= 3h, Irradiation Piva, Olivier; Amougay, Aicha; Pete, Jean-Pierre; Tetrahedron Letters; vol. 32; nb. 32; (1991); p. 3993 - 3996 View in Reaxys

85 %

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, acetonitrile, Time= 3h, Irradiation, various reaction conditions and reagents; further silylethers, Product distribution Piva, Olivier; Amougay, Aicha; Pete, Jean-Pierre; Tetrahedron Letters; vol. 32; nb. 32; (1991); p. 3993 - 3996 View in Reaxys

82 %

With allyltriphenylphopsphonium peroxodisulfate in acetonitrile, Time= 0.5h, Heating Tajbakhsh; Lakouraj; Fadavi; Synthetic Communications; vol. 34; nb. 7; (2004); p. 1173 - 1181 View in Reaxys O

Rx-ID: 25971070 View in Reaxys 231/824 Yield

Conditions & References With hydrogenchloride in acetone, Time= 1h, T= 20 °C Ruan, Jiwu; Li, Xinming; Saidi, Ourida; Xiao, Jianliang; Journal of the American Chemical Society; vol. 130; nb. 8; (2008); p. 2424 - 2425 View in Reaxys O HO

Rx-ID: 26050918 View in Reaxys 232/824 Yield 30 %, 57 %

Conditions & References With Amberlite IRA-120, urea-hydrogen peroxide, 1-n-butyl-3-methylimidazolim bromide, Time= 0.75h, T= 70 °C Bhati, Nishi; Sarma, Kuladip; Goswami, Amrit; Chemistry Letters; vol. 37; nb. 5; (2008); p. 496 - 497 View in Reaxys O HO

Rx-ID: 27938589 View in Reaxys 233/824

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Yield

Conditions & References

25 %, 57 %, With potassium carbonate, phenylboronic acid, [Ru(cyclopentadienyl)(MeCN)3]PF6 in acetonitrile, Time= 16h, T= 90 °C 18 % Helou, Marion; Renaud, Jean-Luc; Demerseman, Bernard; Carreaux, Francois; Bruneau, Christian; New Journal of Chemistry; vol. 32; nb. 6; (2008); p. 929 - 931 View in Reaxys O

N O

Rx-ID: 28158506 View in Reaxys 234/824 Yield

Conditions & References With deuteriated sodium hydroxide, Trimethylacetic acid in D20, [D3]acetonitrile, d4-acetic acid, T= 25 °C , Nef reaction Backstrom, Nicholas; Burton, Neil A.; Turega, Simon; Watt, C. Ian F.; Journal of Physical Organic Chemistry; vol. 21; nb. 7-8; (2008); p. 603 - 613 View in Reaxys O

OH O

Rx-ID: 28203307 View in Reaxys 235/824 Yield 16 %

Conditions & References in dimethyl sulfoxide, Irradiation, Inert atmosphere, Norrish type-II reaction Moorthy, Jarugu Narasimha; Samanta, Subhas; Koner, Apurba L.; Saha, Satyajit; Nau, Werner M.; Journal of the American Chemical Society; vol. 130; nb. 41; (2008); p. 13608 - 13617 View in Reaxys

Rx-ID: 28203308 View in Reaxys 236/824 Yield 15 %

Conditions & References in benzene, Irradiation, Inert atmosphere, Norrish type-II reaction

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Moorthy, Jarugu Narasimha; Samanta, Subhas; Koner, Apurba L.; Saha, Satyajit; Nau, Werner M.; Journal of the American Chemical Society; vol. 130; nb. 41; (2008); p. 13608 - 13617 View in Reaxys O

O O

Rx-ID: 28203309 View in Reaxys 237/824 Yield

Conditions & References in benzene, Irradiation, Inert atmosphere, Norrish type-II reaction, optical yield given as percent de Moorthy, Jarugu Narasimha; Samanta, Subhas; Koner, Apurba L.; Saha, Satyajit; Nau, Werner M.; Journal of the American Chemical Society; vol. 130; nb. 41; (2008); p. 13608 - 13617 View in Reaxys O

O O

Rx-ID: 28203310 View in Reaxys 238/824 Yield 30 %

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Rx-ID: 28203311 View in Reaxys 239/824 Yield

Conditions & References in dimethyl sulfoxide, Irradiation, Inert atmosphere, Norrish type-II reaction, optical yield given as percent de Moorthy, Jarugu Narasimha; Samanta, Subhas; Koner, Apurba L.; Saha, Satyajit; Nau, Werner M.; Journal of the American Chemical Society; vol. 130; nb. 41; (2008); p. 13608 - 13617 View in Reaxys

Rx-ID: 28203322 View in Reaxys 240/824 Yield

O H

Rx-ID: 28214284 View in Reaxys 241/824 Yield 78 %, 2 %

Conditions & References With ethanol, antimony pentafluoride in 1,2-dichloro-ethane, Time= 2h, T= 90 Â°C , stereoselective reaction Saito, Akio; Umakoshi, Masaharu; Yagyu, Naomi; Hanzawa, Yuji; Organic Letters; vol. 10; nb. 9; (2008); p. 1783 - 1785

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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View in Reaxys

Rx-ID: 28214292 View in Reaxys 242/824 Yield

Conditions & References

24 %, 15 %, With ethanol, antimony pentafluoride in 1,2-dichloro-ethane, Time= 4h, T= 90 °C , stereoselective reaction 36 % Saito, Akio; Umakoshi, Masaharu; Yagyu, Naomi; Hanzawa, Yuji; Organic Letters; vol. 10; nb. 9; (2008); p. 1783 - 1785 View in Reaxys

Rx-ID: 28214294 View in Reaxys 243/824 Yield

Conditions & References

22 %, 26 %, With antimony pentafluoride in 1,2-dichloro-ethane, Time= 4h, T= 90 °C , stereoselective reaction 38 % Saito, Akio; Umakoshi, Masaharu; Yagyu, Naomi; Hanzawa, Yuji; Organic Letters; vol. 10; nb. 9; (2008); p. 1783 - 1785 View in Reaxys O

OH 2H

Rx-ID: 28232225 View in Reaxys 244/824 Yield

Conditions & References

83 With tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate, potassium carbonate in acetonitrile, %Spectr., Time= 1h, Inert atmosphere, Reflux 17 %Spectr. Bouziane, Asmae; Carboni, Bertrand; Bruneau, Christian; Carreaux, Francois; Renaud, Jean-Luc; Tetrahedron; vol. 64; nb. 51; (2008); p. 11745 - 11750 View in Reaxys

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O N H O

Rx-ID: 28254889 View in Reaxys 245/824 Yield

Conditions & References

70 %

With caesium carbonate in N,N-dimethyl-formamide, T= 50 °C Knowles, Deborah A.; Mathews, Christopher J.; Tomkinson, Nicholas C. O.; Synlett; nb. 18; (2008); p. 2769 - 2772 View in Reaxys O O

Rx-ID: 28407155 View in Reaxys 246/824 Yield

Conditions & References With hydrogenchloride, water in ethylene glycol, Time= 0.5h Hyder, Zeynab; Ruan, Jiwu; Xiao, Jianliang; Chemistry - A European Journal; vol. 14; nb. 18; (2008); p. 5555 - 5566 View in Reaxys

O Cl Bi O

Rx-ID: 2332695 View in Reaxys 247/824 Yield

Conditions & References

92 %

With triethylamine, palladium diacetate in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 5h, T= 65 °C Barton, Derek H. R.; Ozbalik, Nubar; Ramesh, Manian; Tetrahedron; vol. 44; nb. 18; (1988); p. 5661 - 5668 View in Reaxys With triethylamine, tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane, Time= 3h, T= 80 °C

80 %

Rao, Maddali L.N.; Venkatesh, Varadhachari; Banerjee, Debasis; Tetrahedron; vol. 63; nb. 52; (2007); p. 12917 - 12926 View in Reaxys 78 %

With triethylamine, triphenylphosphine, palladium dichloride in 1,4-dioxane, Time= 4h, T= 80 °C Rao, Maddali L.N.; Venkatesh, Varadhachari; Jadhav, Deepak N.; Tetrahedron Letters; vol. 47; nb. 39; (2006); p. 6975 6978 View in Reaxys O

Rx-ID: 9068319 View in Reaxys 248/824

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Yield

Conditions & References

86 %

With triphenyl phosphite, sodium hydrogencarbonate, (BrBu2Te)2O in water, N,N-dimethyl-formamide, Time= 6h, T= 80 °C Huang, Zheng-Zheng; Tang, Yong; Journal of Organic Chemistry; vol. 67; nb. 15; (2002); p. 5320 - 5326 View in Reaxys

75 %

With water, 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate, Time= 0.116667h, T= 125 °C , p= 2585.74Torr , microwave irradiation Ranu, Brindaban C.; Chattopadhyay, Kalicharan; Jana, Ranjan; Tetrahedron; vol. 63; nb. 1; (2007); p. 155 - 159 View in Reaxys Reaction Steps: 2 1: 90 percent / 1-methyl-3-pentylimidazolium tetrafluoroborate; H2O / 0.04 h / 125 °C / 2585.74 Torr / microwave irradiation 2: 85 percent / 1-methyl-3-pentylimidazolium tetrafluoroborate; H2O / 0.07 h / 125 °C / 2585.74 Torr / microwave irradiation With water, 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate Ranu, Brindaban C.; Chattopadhyay, Kalicharan; Jana, Ranjan; Tetrahedron; vol. 63; nb. 1; (2007); p. 155 - 159 View in Reaxys O

(v2)

Rx-ID: 9650285 View in Reaxys 249/824 Yield 85 %

Conditions & References With bromine, N,N-dimethyl-formamide, zinc, 10 wt. % palladium on activated carbon in tetrahydrofuran, toluene, Time= 48h, T= 20 °C , Fukuyama coupling reaction Mori, Yoshikazu; Seki, Masahiko; Tetrahedron Letters; vol. 45; nb. 39; (2004); p. 7343 - 7345 View in Reaxys

85 %

With bromine, N,N-dimethyl-formamide, zinc, 10 wt. % palladium on activated carbon in tetrahydrofuran, toluene, Time= 48h, T= 20 °C , Fukuyama coupling reaction Mori, Yoshikazu; Seki, Masahiko; Advanced Synthesis and Catalysis; vol. 349; nb. 11-12; (2007); p. 2027 - 2038 View in Reaxys O

HO B HO

Rx-ID: 10327032 View in Reaxys 250/824 Yield 52 %

Conditions & References With [(bpy)Pd(μ-OH)]2(OTf)2 in nitromethane, Time= 24h, Heating Zhao, Baowei; Lu, Xiyan; Organic Letters; vol. 8; nb. 26; (2006); p. 5987 - 5990 View in Reaxys

15 %

With [2,2]bipyridinyl, potassium fluoride, acetic acid, palladium diacetate in tetrahydrofuran, Time= 48h, T= 80 °C Zhao, Baowei; Lu, Xiyan; Tetrahedron Letters; vol. 47; nb. 38; (2006); p. 6765 - 6768 View in Reaxys

12 %

With ammonium chloride, bipyridine-cyclopalladated ferrocenylimine complex in water, Time= 24h, T= 100 °C Yu, Ajuan; Li, Jingya; Cui, Mengjun; Wu, Yangjie; Synlett; nb. 19; (2007); p. 3063 - 3067 View in Reaxys

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O O

Rx-ID: 10396540 View in Reaxys 251/824 Yield

Conditions & References

90 %

With water, 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate, Time= 0.0416667h, T= 125 °C , p= 2585.74Torr , microwave irradiation Ranu, Brindaban C.; Chattopadhyay, Kalicharan; Jana, Ranjan; Tetrahedron; vol. 63; nb. 1; (2007); p. 155 - 159 View in Reaxys

O O

Rx-ID: 10529989 View in Reaxys 252/824 Yield

Conditions & References

32 %, 68 %

With gallium(I) iodide in toluene, Time= 24h, T= 20 °C Green, Shaun P.; Jones, Cameron; Stasch, Andreas; Rose, Richard P.; New Journal of Chemistry; vol. 31; nb. 1; (2007); p. 127 - 134 View in Reaxys O

OH H

Rx-ID: 11110986 View in Reaxys 253/824 Yield

Conditions & References With (R,R)-1,2-diphenylethylenediamine, potassium tert-butylate, cyclohexanone, [(η6-C6H6)Ru(μ-Cl)Cl]2 in tetrahydrofuran, Time= 20h, T= 60 °C Adair, Gareth R. A.; Williams, Jonathan M. J.; Chemical Communications; nb. 25; (2007); p. 2608 - 2609 View in Reaxys O

N N N

O O

N N

N H

Rx-ID: 26012025 View in Reaxys 254/824

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Yield

Conditions & References

32 %, 24 %, in toluene, Time= 16h, UV-irradiation 7% Singh, Pradeep N. D.; Mandel, Sarah M.; Sankaranarayanan, Jagadis; Muthukrishnan, Sivaramakrishnan; Chang, Mingxin; Robinson, Rachel M.; Lahti, Paul M.; Ault, Bruce S.; Gudmundsdottir, Anna D.; Journal of the American Chemical Society; vol. 129; nb. 51; (2007); p. 16263 - 16272 View in Reaxys O O Cl

Rx-ID: 1626908 View in Reaxys 255/824 Yield

Conditions & References With potassium hydroxide, hydrogen, Aliquat 336, tetrakis(triphenylphosphine) palladium(0), 1-decanol in 2,2,4-trimethylpentane, Time= 2h, T= 25 °C , atmospheric pressure

100 %

Perosa, Alvise; Tundo, Pietro; Selva, Maurizio; Canton, Patrizia; Chemical Communications; nb. 43; (2006); p. 4480 - 4482 View in Reaxys 85 %

With 10 wt. % palladium on activated carbon, formic acid, N,N-dimethyl-formamide, Time= 6h, Heating Pandey, Paras N.; Purkayastha, Makhan L.; Synthesis; nb. 10; (1982); p. 876 - 878 View in Reaxys

O O

O S

Rx-ID: 2094694 View in Reaxys 256/824 Yield

Conditions & References

96 %

With ascorbic acid in water, acetonitrile, Time= 10h, T= 20 °C , Irradiation Liu, Qiang; Han, Bing; Liu, Zhengang; Yang, Li; Liu, Zhong-Li; Yu, Wei; Tetrahedron Letters; vol. 47; nb. 11; (2006); p. 1805 - 1807 View in Reaxys

75.6 %

With sodium hydrogen telluride, 18-crown-6 ether in tetrahydrofuran, ethanol, Ambient temperature Huang, Xian; Pi, Jin-Hong; Synthetic Communications; vol. 20; nb. 15; (1990); p. 2297 - 2300 View in Reaxys

75.6 %

With sodium hydrogen telluride, 18-crown-6 ether in tetrahydrofuran, ethanol, Ambient temperature, other η-alkyl-η-keto-sulfones, Product distribution Huang, Xian; Pi, Jin-Hong; Synthetic Communications; vol. 20; nb. 15; (1990); p. 2297 - 2300 View in Reaxys

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Rx-ID: 10099830 View in Reaxys 257/824 Yield 6 %, 31 %, 12 %

Conditions & References With ammonium peroxydisulfate, silver nitrate in N,N-dimethyl-formamide, T= 20 °C Chiba, Shunsuke; Cao, Zhengyan; El Bialy, Serry Atta Atta; Narasaka, Koichi; Chemistry Letters; vol. 35; nb. 1; (2006); p. 18 - 19 View in Reaxys

Si O

Rx-ID: 10118860 View in Reaxys 258/824 Yield 86 %, 10 %

Conditions & References With pyridine, ammonium peroxydisulfate, silver nitrate in N,N-dimethyl-formamide, T= 20 °C Chiba, Shunsuke; Cao, Zhengyan; El Bialy, Serry Atta Atta; Narasaka, Koichi; Chemistry Letters; vol. 35; nb. 1; (2006); p. 18 - 19 View in Reaxys

20 %, 53 %

With ammonium peroxydisulfate, silver nitrate in N,N-dimethyl-formamide, T= 20 °C Chiba, Shunsuke; Cao, Zhengyan; El Bialy, Serry Atta Atta; Narasaka, Koichi; Chemistry Letters; vol. 35; nb. 1; (2006); p. 18 - 19 View in Reaxys

N N

Rx-ID: 10124348 View in Reaxys 259/824 Yield 90 %

Conditions & References With HOF* CH3CN in dichloromethane, Time= 0.0166667h, T= 0 °C Carmeli, Mira; Rozen, Shlomo; Tetrahedron Letters; vol. 47; nb. 5; (2006); p. 763 - 766 View in Reaxys

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N O

Rx-ID: 10160384 View in Reaxys 260/824 Yield

Conditions & References

91 %

O– Na +

P HO

Rx-ID: 10262409 View in Reaxys 261/824 Yield

Conditions & References in water-d2, acetonitrile, Time= 17h, T= 75 °C , pH= 6.8 - 7.5 Hawkins, Michael J.; Powell, Eugene T.; Leo, Gregory C.; Gauthier, Diane A.; Greco, Michael N.; Maryanoff, Bruce; Organic Letters; vol. 8; nb. 16; (2006); p. 3429 - 3431 View in Reaxys O

H H N

Rx-ID: 10304438 View in Reaxys 262/824 Yield

Conditions & References With sodium thiocyanide, Time= 4h, T= 180 - 200 °C Cruz, Alejandro; Contreras, Rosalinda; Padilla-Martinez, Itzia I.; Juarez-Juarez, Minerva; Tetrahedron Asymmetry; vol. 17; nb. 10; (2006); p. 1499 - 1505 View in Reaxys

N B–

Na +

Rx-ID: 10327028 View in Reaxys 263/824 Yield

Conditions & References With 1,3-bis-(diphenylphosphino)propane, water, 1,1'-(1,2-ethanediyl)bisbenzene, chloro(1,5-cyclooctadiene)rhodium(I) dimer in o-xylene, T= 120 °C Ueura, Kenji; Miyamura, Sawako; Satoh, Tetsuya; Miura, Masahiro; Journal of Organometallic Chemistry; vol. 691; nb. 12; (2006); p. 2821 - 2826 View in Reaxys

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O O

Rx-ID: 10397331 View in Reaxys 264/824 Yield

Conditions & References

8 %, 6 %

With palladium dichloride in water, N,N-dimethyl-formamide, Time= 24h, T= 20 °C He, Zhi; Yudin, Andrei K.; Organic Letters; vol. 8; nb. 25; (2006); p. 5829 - 5832 View in Reaxys O

Rx-ID: 10397895 View in Reaxys 265/824 Yield

Conditions & References With potassium hydroxide, acetone, N,N'-bis[o-(diphenylphosphino)benzylidene]-(1S,2S)-diaiminocyclohexane, bis(1,5-cyclooctadiene)diiridium(I) dichloride in isopropyl alcohol, Time= 8h, T= 25 °C Li, Yan-Yun; Zhang, Xue-Qin; Dong, Zhen-Rong; Shen, Wei-Yi; Chen, Gui; Gao, Jing-Xing; Organic Letters; vol. 8; nb. 24; (2006); p. 5565 - 5567 View in Reaxys

Rx-ID: 10445834 View in Reaxys 266/824 Yield

Conditions & References With 2-Amino-4-methylpyridine, benzoic acid, Wilkinson's catalyst in toluene, Time= 4h, T= 130 °C Park, Jung-Woo; Chang, Hoon-Jo; Jun, Chul-Ho; Synlett; nb. 5; (2006); p. 771 - 775 View in Reaxys O

Rx-ID: 11052452 View in Reaxys 267/824 Yield 80.7 %

Conditions & References With cetylpyridinium chloride, dihydrogen peroxide, phosphotungstic acid in chloroform, Time= 12h, T= 60 °C Zhang, Yanfei; Shen, Zongxuan; Tang, Jingting; Zhang, Yan; Kong, Lichun; Zhang, Yawen; Organic and Biomolecular Chemistry; vol. 4; nb. 8; (2006); p. 1478 - 1482 View in Reaxys

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F F

F O N

Rx-ID: 11062460 View in Reaxys 268/824 Yield

Conditions & References With sodium ethanolate in ethanol, T= 20 °C Weiss, Matthias E.; Fischer, Daniel F.; Xin, Zhuo-Qun; Jautze, Sascha; Schweizer, W. Bernd; Peters, Rene; Angewandte Chemie - International Edition; vol. 45; nb. 34; (2006); p. 5694 - 5698 View in Reaxys O HO

Rx-ID: 2015387 View in Reaxys 269/824 Yield

Conditions & References With ammonium peroxydisulfate, copper diacetate, sodium acetate in acetonitrile, T= 100 °C , Yield given. Yields of byproduct given Walling, Cheves; El-Taliawi, Gamil M.; Zhao, Chengxue; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4914 4917 View in Reaxys With hydrogenchloride, sodium hypochlorite, air, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, Time= 0.25h, T= 20 °C , pH= 8.5 - 9.5, Product distribution, Further Variations: Solvents, Reagents, reaction times Bright, Zack R.; Luyeye, Cedric R.; Morton, Angela Ste. Marie; Sedenko, Marina; Landolt, Robert G.; Bronzi, Matthew J.; Bohovic, Katherine M.; Gonser, M. W. Alex; Lapainis, Theodore E.; Hendrickson, William H.; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 684 - 687 View in Reaxys

O HO

Rx-ID: 2015390 View in Reaxys 270/824 Yield

Conditions & References in dichloromethane, Time= 18h, T= 60 - 70 °C , Irradiation, Yield given. Yields of byproduct given Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 16; (1982); p. 2525 - 2538 View in Reaxys With Pd4(μ-COOMe)4(μ-CO)4, Time= 2h, T= 60 °C , Title compound not separated from byproducts Stolarov; Dobrokhotova; Kryukova; Kozitsyna; Gekhman; Vargaftik; Moiseev; Russian Chemical Bulletin; vol. 54; nb. 3; (2005); p. 803 - 806 View in Reaxys

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O H N

N NH 2

Rx-ID: 2043121 View in Reaxys 271/824 Yield

Conditions & References

85 %

With phosphoric acid in water, Time= 4h, T= 95 °C Bhar, Sanjay; Guha, Sharmistha; Synthetic Communications; vol. 35; nb. 9; (2005); p. 1183 - 1188 View in Reaxys

82 %

With [bis(acetoxy)iodo]benzene in water, acetonitrile, Time= 0.5h, Ambient temperature, various aromatic and/or aliphatic semicarbazones investigated; regeneration of carbonyl compounds Chen; Synthesis; nb. 8; (1994); p. 773 - 774 View in Reaxys

78 %

With quinolinium monofluorochromate(VI) in acetonitrile, Time= 3.5h, Heating Tajbakhsh, Mahmoud; Alimohammadi, Kamal; Behmadi, Hossein; Barghamadi, Mohammad; Journal of Chemical Research; nb. 1; (2005); p. 35 - 37 View in Reaxys With copper dichloride in acetonitrile, Time= 0.5h, Heating, Yield given Ram, Ram N.; Varsha, Kiran; Tetrahedron Letters; vol. 32; nb. 41; (1991); p. 5829 - 5832 View in Reaxys With tellurium oxide, lithium bromide in acetic acid, Heating, Yield given Bergman, Jan; Engman, Lars; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 35; nb. 7; (1980); p. 882 - 884 View in Reaxys O

O N N N

Rx-ID: 9070867 View in Reaxys 272/824 Yield 78 %

Conditions & References With samarium diiodide in tetrahydrofuran, T= 20 °C Fan, Xuesen; Zhang, Yongmin; Tetrahedron Letters; vol. 43; nb. 10; (2002); p. 1863 - 1865 View in Reaxys

78 %

With samarium diiodide in tetrahydrofuran, T= 20 °C Fan, Xuesen; Zhang, Xinying; Zhang, Yongmin; Journal of Chemical Research; nb. 11; (2005); p. 750 - 752 View in Reaxys O O

Rx-ID: 9771479 View in Reaxys 273/824 Yield

Conditions & References With tert.-butylhydroperoxide, air, (Pd(IiPr)Cl2)2, silver trifluoromethanesulfonate in methanol, Time= 48h, T= 35 °C , Wacker oxidation, Title compound not separated from byproducts

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Cornell, Candace N.; Sigman, Matthew S.; Journal of the American Chemical Society; vol. 127; nb. 9; (2005); p. 2796 - 2797 View in Reaxys

Li N O

NH 2

NH O

Rx-ID: 9867293 View in Reaxys 274/824 Yield

Conditions & References

5 % Spectr., in tetrahydrofuran, cyclohexane, toluene, Time= 3h, T= -78 °C 7 % Spectr., Di Nunno, Leonardo; Scilimati, Antonio; Vitale, Paola; Tetrahedron; vol. 61; nb. 10; (2005); p. 2623 - 2630 40 % View in Reaxys Spectr., 40 % Spectr. HO

O OH H HO

Rx-ID: 9873547 View in Reaxys 275/824 Yield 84 %

Conditions & References With [(C4Ph4COHOCC4Ph4)(μ-H)][(CO)4Ru2], Novozym(R) 435, 2,4-dimethylpentan-3-one in toluene, Time= 40h, T= 70 °C , p= 142.511Torr Verzijl, Gerard K.M.; De Vries, Johannes G.; Broxterman, Quirinus B.; Tetrahedron Asymmetry; vol. 16; nb. 9; (2005); p. 1603 - 1610 View in Reaxys

O HO

Rx-ID: 9955940 View in Reaxys 276/824 Yield 17 %, 34 %

Conditions & References With [bis(acetoxy)iodo]benzene, iodine in dichloromethane, Time= 0.0333333h, T= 20 °C , Irradiation

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Bietti, Massimo; Gente, Giacomo; Salamone, Michela; Journal of Organic Chemistry; vol. 70; nb. 17; (2005); p. 6820 - 6826 View in Reaxys O

Rx-ID: 9963857 View in Reaxys 277/824 Yield

Conditions & References With gallium(III) triflate, (S,S)-4-tBu-2,6-bis[2-(HOCPh2-)pyrazolidin-1-ylmethyl]phenol in ethanol, water, Time= 36h, T= 0 5 °C , asymmetric Mukaiyama aldol reaction, Product distribution, Further Variations: Catalysts, Solvents Li, Hui-Jing; Tian, Hong-Yu; Wu, Yan-Chao; Chen, Yong-Jun; Liu, Li; Wang, Dong; Li, Chao-Jun; Advanced Synthesis and Catalysis; vol. 347; nb. 9; (2005); p. 1247 - 1256 View in Reaxys O

Rx-ID: 9992259 View in Reaxys 278/824 Yield

Conditions & References

74 %

With water, oxygen, copper dichloride in acetonitrile, Time= 2h, T= 40 °C , p= 760Torr Tokunaga, Makoto; Shirogane, Yuki; Aoyama, Hiroshi; Obora, Yasushi; Tsuji, Yasushi; Journal of Organometallic Chemistry; vol. 690; nb. 23; (2005); p. 5378 - 5382 View in Reaxys

O HO

HO HO

Rx-ID: 10070514 View in Reaxys 279/824 Yield 6 %, 79 %, 3 %, 7 %

Conditions & References With samarium diiodide, water in tetrahydrofuran, Time= 0.166667h, T= 20 °C , Further byproducts given Kamochi, Yasuko; Kudo, Tadahiro; Masuda, Toshinobu; Takadate, Akira; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 8; (2005); p. 1017 - 1020 View in Reaxys

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Rx-ID: 10082086 View in Reaxys 280/824 Yield

Conditions & References in benzene-d6, T= 25 °C , UV-irradiation, Quantum yield, Further Variations: Solvents Singhal, Nidhi; Koner, Apurba L.; Mal, Prasenjit; Venugopalan, Paloth; Nau, Werner M.; Moorthy, Jarugu Narasimha; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14375 - 14382 View in Reaxys

O OH

O O

Rx-ID: 10082087 View in Reaxys 281/824 Yield

Conditions & References in benzene-d6, T= 25 °C , UV-irradiation, Product distribution, Quantum yield, Further Variations: Solvents Singhal, Nidhi; Koner, Apurba L.; Mal, Prasenjit; Venugopalan, Paloth; Nau, Werner M.; Moorthy, Jarugu Narasimha; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14375 - 14382 View in Reaxys

Rx-ID: 10085826 View in Reaxys 282/824 Yield

Conditions & References in benzene-d6, T= 25 °C , UV-irradiation, Product distribution, Further Variations: Solvents

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Singhal, Nidhi; Koner, Apurba L.; Mal, Prasenjit; Venugopalan, Paloth; Nau, Werner M.; Moorthy, Jarugu Narasimha; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14375 - 14382 View in Reaxys

Rx-ID: 10085827 View in Reaxys 283/824 Yield

Conditions & References in benzene-d6, T= 25 °C , UV-irradiation, Product distribution, Further Variations: Solvents Singhal, Nidhi; Koner, Apurba L.; Mal, Prasenjit; Venugopalan, Paloth; Nau, Werner M.; Moorthy, Jarugu Narasimha; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14375 - 14382 View in Reaxys H

Rx-ID: 10417442 View in Reaxys 284/824 Yield

Conditions & References With potassium tert-butylate, [Ru(η5-Ph4MeCp)(CO)2Cl] in tetrahydrofuran, toluene, Time= 2h, T= 50 °C , Title compound not separated from byproducts Martin-Matute, Belen; Bogar, Krisztian; Edin, Michaela; Kaynak, F. Betuel; Baeckvall, Jan-E.; Chemistry - A European Journal; vol. 11; nb. 20; (2005); p. 5832 - 5842 View in Reaxys

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 12937586 View in Reaxys 285/824 Yield

Conditions & References Reaction Steps: 3 1: 40 percent / (diacetoxy)iodobenzene; I2 / CH2Cl2 / 0.02 h / 20 °C / Irradiation 2: tetrahydrofuran

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3: 34 percent / (diacetoxy)iodobenzene; I2 / CH2Cl2 / 0.03 h / 20 °C / Irradiation With [bis(acetoxy)iodo]benzene, iodine in tetrahydrofuran, dichloromethane Bietti, Massimo; Gente, Giacomo; Salamone, Michela; Journal of Organic Chemistry; vol. 70; nb. 17; (2005); p. 6820 - 6826 View in Reaxys O

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 12958681 View in Reaxys 286/824 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran 2: 34 percent / (diacetoxy)iodobenzene; I2 / CH2Cl2 / 0.03 h / 20 °C / Irradiation With [bis(acetoxy)iodo]benzene, iodine in tetrahydrofuran, dichloromethane Bietti, Massimo; Gente, Giacomo; Salamone, Michela; Journal of Organic Chemistry; vol. 70; nb. 17; (2005); p. 6820 - 6826 View in Reaxys

S S

Rx-ID: 4338747 View in Reaxys 287/824 Yield

Conditions & References

99 %

With silica gel, copper(II) nitrate in tetrachloromethane, Time= 0.25h, Ambient temperature Lee, Jong Gun; Hwang, Je Pil; Chemistry Letters; nb. 7; (1995); p. 507 - 508 View in Reaxys

94 %

With silica gel, ferric nitrate in hexane, Time= 0.166667h, T= 50 °C Hirano, Masao; Ukawa, Ken; Yakabe, Shigetaka; Morimoto, Takashi; Organic Preparations and Procedures International; vol. 29; nb. 4; (1997); p. 480 - 484 View in Reaxys

92 %

With potassium permanganate, tetrachlorosilane in acetonitrile, Time= 0.116667h, T= 20 °C Firouzabadi, Habib; Hazarkhani, Hassan; Hassani, Hassan; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 2; (2004); p. 403 - 409 View in Reaxys O S

Rx-ID: 4339022 View in Reaxys 288/824 Yield 99 %

Conditions & References With silica gel, copper(II) nitrate in tetrachloromethane, Time= 1h, Ambient temperature Lee, Jong Gun; Hwang, Je Pil; Chemistry Letters; nb. 7; (1995); p. 507 - 508 View in Reaxys

99 %

With silica gel, ferric nitrate in hexane, Time= 0.5h, T= 40 °C

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Hirano, Masao; Ukawa, Ken; Yakabe, Shigetaka; Morimoto, Takashi; Synthetic Communications; vol. 27; nb. 9; (1997); p. 1527 - 1533 View in Reaxys 92 %

With zinc dichromate(VI) in acetonitrile, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Hassani, Hassan; Sobhani, Sara; Synthetic Communications; vol. 34; nb. 11; (2004); p. 1967 - 1972 View in Reaxys

Si O

Rx-ID: 5280952 View in Reaxys 289/824 Yield

Conditions & References

93 %

With N-hydroxyphthalimide, oxygen, cobalt(II) benzoate in acetonitrile, Time= 2h, T= 20 °C Karimi, Babak; Rajabi, Jamshid; Organic Letters; vol. 6; nb. 17; (2004); p. 2841 - 2844 View in Reaxys

92 %

With zinc dichromate(VI), T= 20 °C Firouzabadi, Habib; Hassani, Hassan; Gholizadeh, Mostafa; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 7; (2004); p. 1417 - 1422 View in Reaxys

90 %

With potassium permanganate, tetrachlorosilane in acetonitrile, Time= 0.45h, T= 20 °C Firouzabadi, Habib; Hazarkhani, Hassan; Hassani, Hassan; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 2; (2004); p. 403 - 409 View in Reaxys

80 %

With manganese(IV) oxide, aluminium trichloride in acetonitrile, Time= 0.166667h, Heating, Oxidation Firouzabadi, Habib; Etemadi, Shahrad; Karimi, Babak; Jarrahpour, Ali Asghar; Synthetic Communications; vol. 29; nb. 24; (1999); p. 4333 - 4339 View in Reaxys

Rx-ID: 9549929 View in Reaxys 290/824 Yield 92 %

Conditions & References With zinc dichromate(VI), T= 20 °C Firouzabadi, Habib; Hassani, Hassan; Gholizadeh, Mostafa; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 7; (2004); p. 1417 - 1422 View in Reaxys

90 %

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80 %

With allyltriphenylphopsphonium peroxodisulfate in acetonitrile, Time= 0.5h, Heating Tajbakhsh; Lakouraj; Fadavi; Synthetic Communications; vol. 34; nb. 7; (2004); p. 1173 - 1181 View in Reaxys

O OH H

O HO

Rx-ID: 9581471 View in Reaxys 291/824 Yield

Conditions & References

62 %, 38 %

With Novozym 435, potassium tert-butylate, sodium carbonate, [2,3,4,5-Ph4(η5-C4CNH(i-Pr))]Ru(CO)2Cl in toluene, Time= 96h, T= 25 °C Choi, Jun Ho; Choi, Yoon Kyung; Kim, Yu Hwan; Park, Eun Sil; Kim, Eun Jung; Kim, Mahn-Joo; Park, Jaiwook; Journal of Organic Chemistry; vol. 69; nb. 6; (2004); p. 1972 - 1977 View in Reaxys O

Rx-ID: 9651373 View in Reaxys 292/824 Yield

Conditions & References

89 %

With N-bromobis(p-toluenesulfonyl)amine in tetrachloromethane, Time= 3.5h, T= 20 °C Ghorbani-Vaghei, Ramin; Khazaei, Ardeshir; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 6; (2004); p. 1169 - 1173 View in Reaxys O

Rx-ID: 9666668 View in Reaxys 293/824 Yield

Conditions & References

47 %

With tris(dipivaloylmethanato)europium(III) in hexane, benzene, Time= 24h, T= 25 °C Tsvelikhovsky, Dmitry; Gelman, Dmitri; Molander, Gary A.; Blum, Jochanan; Organic Letters; vol. 6; nb. 12; (2004); p. 1995 - 1997 View in Reaxys O

H 2N O O

Rx-ID: 9686969 View in Reaxys 294/824

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Yield

Conditions & References

83 %

With trimethylsilyl trifluoromethanesulfonate, water in toluene, T= -78 - 20 °C Seppi, Michael; Kalkofen, Rainer; Reupohl, Jens; Froehlich, Roland; Hoppe, Dieter; Angewandte Chemie - International Edition; vol. 43; nb. 11; (2004); p. 1423 - 1427 View in Reaxys

O H N

N NH 2

Rx-ID: 9741312 View in Reaxys 295/824 Yield 100 %

Conditions & References With caro's acid, silica gel in dichloromethane, Time= 0.116667h, Heating Tajbakhsh, Mahmood; Lakouraj, Moslem-Mansor; Gholami, Mohammad-Hosein; Ramzanian-Lehmali, Farhad; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 9; (2004); p. 1731 - 1736 View in Reaxys O

O (v2)

Rx-ID: 9778931 View in Reaxys 296/824 Yield 93 %

Conditions & References With bis(acetylacetonate)nickel(II), para-fluorostyrene, 2-(2-(diphenylphosphino)ethyl)pyridine in tetrahydrofuran, Time= 0.0833333h, T= 23 °C Zhang, Yongda; Rovis, Tomislav; Journal of the American Chemical Society; vol. 126; nb. 49; (2004); p. 15964 - 15965 View in Reaxys O O

Rx-ID: 23659319 View in Reaxys 297/824 Yield

Conditions & References 7 With nitric acid, 1-n-butyl-3-methylimidazolium methanesulfonate in water, Time= 80h, Heating / reflux Patent; THE QUEEN'S UNIVERSITY OF BELFAST; JP2004/523477; (2004); (A) Japanese View in Reaxys O

Rx-ID: 2063591 View in Reaxys 298/824 Yield 68 %

Conditions & References With molecular sieve, pyridinium chlorochromate in dichloromethane, Time= 10h, T= 20 °C Fernandes, Rodney A.; Kumar, Pradeep; Tetrahedron Letters; vol. 44; nb. 6; (2003); p. 1275 - 1278

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View in Reaxys 47 %

With 1,10-Phenanthroline, oxygen, copper(l) chloride in benzene, Time= 2h, Heating Jallabert, C.; Riviere, H.; Tetrahedron; vol. 36; nb. 82; (1980); p. 1191 - 1194 View in Reaxys O HO

Rx-ID: 8691233 View in Reaxys 299/824 Yield

Conditions & References

74 %, 12 %

With (2-methyl-4-phenyl-1-oxabuta-1,3-diene)tricarbonyliron(0) in tetrahydrofuran, Time= 1.5h, Irradiation Uma, Ramalinga; Gouault, Nicolas; Crevisy, Christophe; Gree, Rene; Tetrahedron Letters; vol. 44; nb. 33; (2003); p. 6187 6190 View in Reaxys

73 %, 10 %

With iron pentacarbonyl in tetrahydrofuran, Irradiation, Title compound not separated from byproducts Crevisy, Christophe; Wietrich, Marina; Le Boulaire, Virginie; Uma, Ramalinga; Gree, Rene; Tetrahedron Letters; vol. 42; nb. 3; (2001); p. 395 - 398 View in Reaxys O O

O 2H

Rx-ID: 9312427 View in Reaxys 300/824 Yield

Conditions & References Stage 1: in diethyl ether, Time= 1h, T= 20 °C Stage 2: With tetradeuterioacetic acid in tetrahydrofuran, diethyl ether, Time= 0.5h, T= -78 °C , Title compound not separated from byproducts Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys With ethylene glycol-d2, methyllithium in tetrahydrofuran, Product distribution, Further Variations: Reagents Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys Stage 1: in diethyl ether, Time= 1h, T= 20 °C Stage 2: With tetradeuterioacetic acid in tetrahydrofuran, diethyl ether, Time= 0.5h, T= -78 °C , Further stages. Title compound not separated from byproducts. Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys O

Li O

Rx-ID: 9319580 View in Reaxys 301/824

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Yield

Conditions & References

78 %

With copper(l) chloride, lithium chloride in tetrahydrofuran Dieter, R. Karl; Sharma, Ram R.; Yu, Huayun; Gore, Vinayak K.; Tetrahedron; vol. 59; nb. 7; (2003); p. 1083 - 1094 View in Reaxys O HO

B HO

Rx-ID: 9319623 View in Reaxys 302/824 Yield

Conditions & References

71 % Chromat.

With bis-triphenylphosphine-palladium(II) chloride, potassium phosphate in toluene, Time= 4h, T= 80 °C , Suzuki-Miyaura coupling reaction Urawa, Yoshio; Ogura, Katsuyuki; Tetrahedron Letters; vol. 44; nb. 2; (2003); p. 271 - 273 View in Reaxys O O

Rx-ID: 9326515 View in Reaxys 303/824 Yield

Conditions & References

32 %, 40 %

With boron trifluoride diethyl etherate in dichloromethane, Time= 2h, T= -78 °C Gansaeuer, Andreas; Fielenbach, Doris; Stock, Christoph; Geich-Gimbel, Daniel; Advanced Synthesis and Catalysis; vol. 345; nb. 8; (2003); p. 1017 - 1030 View in Reaxys O

H 2N (v2)

H 2N

Rx-ID: 9329056 View in Reaxys 304/824 Yield

Conditions & References

15 %, 25 %, Stage 1: With methyltriisopropoxytitanium(IV), lithium isopropoxide in tetrahydrofuran, T= 20 °C 18 % Stage 2: With water, Further stages. Wiedemann, Stefan; Frank, Daniel; Winsel, Harald; De Meijere, Armin; Organic Letters; vol. 5; nb. 5; (2003); p. 753 - 755 View in Reaxys

Rx-ID: 9347462 View in Reaxys 305/824 Yield 83 %

Conditions & References With boron trifluoride diethyl etherate in dichloromethane, Time= 3h, T= -40 - -30 °C , Product distribution, Further Variations: Catalysts Gansaeuer, Andreas; Fielenbach, Doris; Stock, Christoph; Geich-Gimbel, Daniel; Advanced Synthesis and Catalysis; vol. 345; nb. 8; (2003); p. 1017 - 1030

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View in Reaxys

O N

N P N

Rx-ID: 9351092 View in Reaxys 306/824 Yield 85 %

Conditions & References With sulfuric acid in benzene, Time= 4h, Heating Grison, Claude; Thomas, Antoine; Coutrot, Frederic; Coutrot, Philippe; Tetrahedron; vol. 59; nb. 12; (2003); p. 2101 2123 View in Reaxys O O

Rx-ID: 9390459 View in Reaxys 307/824 Yield 26 %, 74 % Chromat.

Conditions & References With peracetic acid, [((phen)2(H2O)FeIII)2(μ-O)](ClO4)2 in water, acetonitrile, Time= 0.0833333h, cooling Dubois, Geraud; Murphy, Andrew; Daniel; Stack; Organic Letters; vol. 5; nb. 14; (2003); p. 2469 - 2472 View in Reaxys

O H

I O

Rx-ID: 9402083 View in Reaxys 308/824 Yield

Conditions & References With 4 A molecular sieve, potassium carbonate, 9-bora-bicyclo[3.3.1]nonane in toluene, Time= 20h, T= 20 °C , Product distribution, Further Variations: Reagents, Solvents, Temperatures, reaction times Mukaiyama, Teruaki; Takuwa, Tomofumi; Yamane, Keiko; Imachi, Shouhei; Bulletin of the Chemical Society of Japan; vol. 76; nb. 4; (2003); p. 813 - 823 View in Reaxys O

N O

Rx-ID: 9421205 View in Reaxys 309/824

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Yield

Conditions & References

7 % Spectr., Stage 1:T= 400 °C , p= 0.0015Torr , flash vacuum thermolysis 93 % Stage 2: With hydrogenchloride in methanol, water, T= -50 - 20 °C , Further stages. Spectr. Bartnik, Romuald; Baylere, Patrick; Chrostowska, Anna; Galindo, Alberto; Lesniak, Stanislaw; Pfister-Guillouzo, Genevieve; European Journal of Organic Chemistry; nb. 13; (2003); p. 2475 - 2479 View in Reaxys O

O Te

Rx-ID: 9424045 View in Reaxys 310/824 Yield

Conditions & References

59 % Spectr.

With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Time= 2h, T= 0 °C , Product distribution Al-Rubaie, Ali Z.; Yousif, Lina Z.; Al-Ba'aj, Ammar K.; Journal of Organometallic Chemistry; vol. 673; nb. 1-2; (2003); p. 40 - 46 View in Reaxys Cl

Rx-ID: 9426199 View in Reaxys 311/824 Yield 48 % Spectr.

Conditions & References With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Time= 2h, T= 0 °C , Product distribution Al-Rubaie, Ali Z.; Yousif, Lina Z.; Al-Ba'aj, Ammar K.; Journal of Organometallic Chemistry; vol. 673; nb. 1-2; (2003); p. 40 - 46 View in Reaxys O

O Zn I

(v2)

Rx-ID: 9536672 View in Reaxys 312/824 Yield 74 %

Conditions & References With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, Heating, Negishi-type cross-coupling Wang, Donghui; Zhang, Zhaoguo; Organic Letters; vol. 5; nb. 24; (2003); p. 4645 - 4648 View in Reaxys O

O Na + O–

(v2)

Rx-ID: 9573577 View in Reaxys 313/824 Yield 78 %

Conditions & References Stage 1: With chloroformic acid ethyl ester in tetrahydrofuran, Time= 0.25h, T= 20 °C Stage 2: With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, Time= 14h, T= 70 °C , Negishi-type cross-coupling Wang, Donghui; Zhang, Zhaoguo; Organic Letters; vol. 5; nb. 24; (2003); p. 4645 - 4648

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View in Reaxys O H 2N

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 14301381 View in Reaxys 314/824 Yield

Conditions & References Reaction Steps: 5 1.1: POCl3; Et3N / diethyl ether / 1.25 h / -5 - 20 °C 2.1: Et3N / diethyl ether / -20 - 20 °C 3.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -50 - 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -50 °C 4.2: 91 percent / H2O / tetrahydrofuran; hexane / -50 °C 5.1: 85 percent / aq. H2SO4 / benzene / 4 h / Heating With n-butyllithium, sulfuric acid, triethylamine, trichlorophosphate in tetrahydrofuran, diethyl ether, hexane, benzene Grison, Claude; Thomas, Antoine; Coutrot, Frederic; Coutrot, Philippe; Tetrahedron; vol. 59; nb. 12; (2003); p. 2101 2123 View in Reaxys O Cl

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 14317284 View in Reaxys 315/824 Yield

Conditions & References Reaction Steps: 4 1.1: Et3N / diethyl ether / -20 - 20 °C 2.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -50 - 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -50 °C 3.2: 91 percent / H2O / tetrahydrofuran; hexane / -50 °C 4.1: 85 percent / aq. H2SO4 / benzene / 4 h / Heating With n-butyllithium, sulfuric acid, triethylamine in tetrahydrofuran, diethyl ether, hexane, benzene Grison, Claude; Thomas, Antoine; Coutrot, Frederic; Coutrot, Philippe; Tetrahedron; vol. 59; nb. 12; (2003); p. 2101 2123 View in Reaxys

N O

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 14318405 View in Reaxys 316/824 Yield

Conditions & References Reaction Steps: 3 1.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -50 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -50 °C 2.2: 91 percent / H2O / tetrahydrofuran; hexane / -50 °C 3.1: 85 percent / aq. H2SO4 / benzene / 4 h / Heating With n-butyllithium, sulfuric acid in tetrahydrofuran, hexane, benzene

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Grison, Claude; Thomas, Antoine; Coutrot, Frederic; Coutrot, Philippe; Tetrahedron; vol. 59; nb. 12; (2003); p. 2101 2123 View in Reaxys

O N O P

bis<chloro(η3-1,3-diphenylallyl)palladium>

N N

Rx-ID: 14318472 View in Reaxys 317/824 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -50 °C 1.2: 91 percent / H2O / tetrahydrofuran; hexane / -50 °C 2.1: 85 percent / aq. H2SO4 / benzene / 4 h / Heating With n-butyllithium, sulfuric acid in tetrahydrofuran, hexane, benzene Grison, Claude; Thomas, Antoine; Coutrot, Frederic; Coutrot, Philippe; Tetrahedron; vol. 59; nb. 12; (2003); p. 2101 2123 View in Reaxys O

Rx-ID: 2068078 View in Reaxys 318/824 Yield 97 %

Conditions & References With tin(ll) chloride, palladium dichloride in water, Time= 0.025h, microwave irradiation Hosseinzadeh, Rahman; Sharifi, Ali; Tabar-Heydar, Kourosh; Mohsenzadeh, Farshid; Monatshefte fur Chemie; vol. 133; nb. 11; (2002); p. 1413 - 1415 View in Reaxys

96 %

With water, manganese(III) acetylacetonate in chloroform, Time= 1h, Heating, Hydrolysis Kamal; Arifuddin; Rao; Synlett; nb. 10; (2000); p. 1482 - 1484 View in Reaxys

90 %

With sodium perborate, sodium hydroxide, potassium dihydrogenphosphate, water in tert-butyl alcohol, Time= 48h, T= 60 °C Enders, Dieter; Bhushan, Vidya; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 42; nb. 12; (1987); p. 1595 1596 View in Reaxys

95 % Chromat.

With porcin pancreatic lipase in water, acetone, Time= 48h, T= 20 °C , Hydrolysis Mino, Takashi; Matsuda, Terumi; Hiramatsu, Dai; Yamashita, Masakazu; Tetrahedron Letters; vol. 41; nb. 9; (2000); p. 1461 - 1463 View in Reaxys

95 % Chromat.

With montmorillonite K-10, Time= 0.0333333h, microwave irradiation Hosseinzadeh, Rahmam; Sharifi, Ali; Mirzaei, Mojtaba; Tabar Heydar, Kourosh; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 57; nb. 8; (2002); p. 961 - 962 View in Reaxys

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O O

Rx-ID: 9004804 View in Reaxys 319/824 Yield

Conditions & References

5 % Spectr., 11 % Spectr., 10 % Spectr., 64 % Spectr.

With magnesium, T= 600 °C , p= 0.01 - 0.1Torr , Further byproducts. Title compound not separated from byproducts. Aitken, R. Alan; Hodgson, Philip K.G.; Morrison, John J.; Oyewale, Adebayo O.; Journal of the Chemical Society. Perkin Transactions 1; nb. 3; (2002); p. 402 - 415 View in Reaxys

O H 2N

N N H 2N

N H N

Rx-ID: 9023591 View in Reaxys 320/824 Yield 8 %, 39 %, 8 %, 5 %

Conditions & References With 2,2'-azobis(isobutyronitrile), tri-n-butyl-tin hydride in benzene, Heating, Product distribution Benati, Luisa; Leardini, Rino; Minozzi, Matteo; Nanni, Daniele; Spagnolo, Piero; Strazzari, Samantha; Zanardi, Giuseppe; Calestani, Gianluca; Tetrahedron; vol. 58; nb. 18; (2002); p. 3485 - 3492 View in Reaxys

O Na +

B–

Rx-ID: 9143944 View in Reaxys 321/824

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Yield

Conditions & References

46 % Chromat.

With [(1,5-cyclooctadiene)2RhCl]2, 1,3-bis-(diphenylphosphino)propane in toluene, Time= 2h, T= 100 °C Oguma, Kazuaki; Miura, Masahiro; Satoh, Tetsuya; Nomura, Masakatsu; Journal of Organometalic Chemistry; vol. 648; nb. 1-2; (2002); p. 297 - 301 View in Reaxys

O O Na +

B–

Rx-ID: 9143946 View in Reaxys 322/824 Yield

Conditions & References With [(1,5-cyclooctadiene)2RhCl]2, 1,3-bis-(diphenylphosphino)propane in toluene, Time= 2h, T= 100 °C Oguma, Kazuaki; Miura, Masahiro; Satoh, Tetsuya; Nomura, Masakatsu; Journal of Organometalic Chemistry; vol. 648; nb. 1-2; (2002); p. 297 - 301 View in Reaxys O HO

Si O

Rx-ID: 9150730 View in Reaxys 323/824 Yield

Conditions & References

41 %, 52 %

With potassium tert-butylate in tetrahydrofuran, T= -78 °C Ma, Yuan; Heteroatom Chemistry; vol. 13; nb. 4; (2002); p. 310 - 315 View in Reaxys

O Si

Rx-ID: 9157368 View in Reaxys 324/824 Yield 96 %

Conditions & References With 18-crown-6 ether, potassium hexamethylsilazane in tetrahydrofuran, T= -78 °C Ma, Yuan; Heteroatom Chemistry; vol. 13; nb. 4; (2002); p. 310 - 315 View in Reaxys O O

Mg Br

Rx-ID: 9208005 View in Reaxys 325/824 Yield

Conditions & References Stage 1: With 1-hydroxy-7-aza-benzotriazole, resin-CH2-NH-OBn, diisopropyl-carbodiimide, Time= 5h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 18h, T= 20 °C , Grignard reaction

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Tice, Colin M.; Michelotti, Enrique L.; Mata, Ernesto G.; Nicolas, Ernesto; Garcia, Javier; Albericio, Fernando; Tetrahedron Letters; vol. 43; nb. 42; (2002); p. 7491 - 7494 View in Reaxys O

Rx-ID: 9246832 View in Reaxys 326/824 Yield

Conditions & References

18 %

With potassium permanganate, iron(III) chloride in acetone, Time= 16h, T= -78 - 20 °C Lai, Sheng; Lee, Donald G.; Tetrahedron; vol. 58; nb. 49; (2002); p. 9879 - 9887 View in Reaxys O

O F O

bis<chloro(η3-1,3-diphenylallyl)palladium>

F F

Rx-ID: 14734142 View in Reaxys 327/824 Yield

Conditions & References Reaction Steps: 3 1: 73 percent / Pd(DBA)2 / tetrahydrofuran / 12 h / 20 °C 2: 97 percent / Na2EDTA; di(chloromethyl)dioxirane; Bu4NHSO4 / acetonitrile 3: 52 percent / tBuOK / tetrahydrofuran / -78 °C With di(chloromethyl)dioxirane, potassium tert-butylate, tetra(n-butyl)ammonium hydrogensulfate, edetate disodium, bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran, acetonitrile Ma, Yuan; Heteroatom Chemistry; vol. 13; nb. 4; (2002); p. 310 - 315 View in Reaxys 2H

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 14734851 View in Reaxys 328/824 Yield

Conditions & References Reaction Steps: 4 1: Et3N; DMAP / CH2Cl2 / 15 h / 0 °C 2: 70 percent / Pd(DBA)2 / tetrahydrofuran / 12 h / 20 °C 3: 93 percent / Na2EDTA; di(chloromethyl)dioxirane; Bu4NHSO4 / acetonitrile 4: 96 percent / KN(TMS)2; 18-Crown-6 / tetrahydrofuran / -78 °C With dmap, 18-crown-6 ether, di(chloromethyl)dioxirane, tetra(n-butyl)ammonium hydrogensulfate, edetate disodium, potassium hexamethylsilazane, triethylamine, bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran, dichloromethane, acetonitrile Ma, Yuan; Heteroatom Chemistry; vol. 13; nb. 4; (2002); p. 310 - 315 View in Reaxys O

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 14735812 View in Reaxys 329/824

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Yield

Conditions & References Reaction Steps: 2 1: 97 percent / Na2EDTA; di(chloromethyl)dioxirane; Bu4NHSO4 / acetonitrile 2: 52 percent / tBuOK / tetrahydrofuran / -78 °C With di(chloromethyl)dioxirane, potassium tert-butylate, tetra(n-butyl)ammonium hydrogensulfate, edetate disodium in tetrahydrofuran, acetonitrile Ma, Yuan; Heteroatom Chemistry; vol. 13; nb. 4; (2002); p. 310 - 315 View in Reaxys O

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 14744174 View in Reaxys 330/824 Yield

Conditions & References Reaction Steps: 4 1: Et3N; DMAP / CH2Cl2 / 15 h / 0 °C 2: 73 percent / Pd(DBA)2 / tetrahydrofuran / 12 h / 20 °C 3: 97 percent / Na2EDTA; di(chloromethyl)dioxirane; Bu4NHSO4 / acetonitrile 4: 52 percent / tBuOK / tetrahydrofuran / -78 °C With dmap, di(chloromethyl)dioxirane, potassium tert-butylate, tetra(n-butyl)ammonium hydrogensulfate, edetate disodium, triethylamine, bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran, dichloromethane, acetonitrile Ma, Yuan; Heteroatom Chemistry; vol. 13; nb. 4; (2002); p. 310 - 315 View in Reaxys 2H

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 14767987 View in Reaxys 331/824 Yield

Conditions & References Reaction Steps: 2 1: 93 percent / Na2EDTA; di(chloromethyl)dioxirane; Bu4NHSO4 / acetonitrile 2: 96 percent / KN(TMS)2; 18-Crown-6 / tetrahydrofuran / -78 °C With 18-crown-6 ether, di(chloromethyl)dioxirane, tetra(n-butyl)ammonium hydrogensulfate, edetate disodium, potassium hexamethylsilazane in tetrahydrofuran, acetonitrile Ma, Yuan; Heteroatom Chemistry; vol. 13; nb. 4; (2002); p. 310 - 315 View in Reaxys 2

bis<chloro(η3-1,3-diphenylallyl)palladium>

O F F

Rx-ID: 14768284 View in Reaxys 332/824 Yield

Conditions & References Reaction Steps: 3 1: 70 percent / Pd(DBA)2 / tetrahydrofuran / 12 h / 20 °C 2: 93 percent / Na2EDTA; di(chloromethyl)dioxirane; Bu4NHSO4 / acetonitrile 3: 96 percent / KN(TMS)2; 18-Crown-6 / tetrahydrofuran / -78 °C With 18-crown-6 ether, di(chloromethyl)dioxirane, tetra(n-butyl)ammonium hydrogensulfate, edetate disodium, potassium hexamethylsilazane, bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran, acetonitrile

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Ma, Yuan; Heteroatom Chemistry; vol. 13; nb. 4; (2002); p. 310 - 315 View in Reaxys O

Rx-ID: 1986664 View in Reaxys 333/824 Yield

Conditions & References

92 %

With oxygen, lithium cyclohexylisopropylamide in dimethyl sulfoxide, Time= 16h, Ambient temperature Kulp, Stuart S.; McGee, Michael J.; Journal of Organic Chemistry; vol. 48; nb. 22; (1983); p. 4097 - 4098 View in Reaxys With cultured suspension cells of cotton (Gossypium hirsutum), T= 25 °C , pH= 5.8, X Hamada, Hiroki; Tanaka, Toshinori; Furuya, Tsutomu; Takahata, Hiroki; Nemoto, Hideo; Tetrahedron Letters; vol. 42; nb. 5; (2001); p. 909 - 911 View in Reaxys O

Rx-ID: 8813269 View in Reaxys 334/824 Yield

Conditions & References With Merulius tremellosus ono991 in acetone, Time= 72h, T= 28 °C , Title compound not separated from byproducts Hage, Annemarie; Petra, Danielle G.I.; Field, Jim A.; Schipper, Dick; Wijnberg, Joannes B.P.A.; Kamer, Paul C.J.; Reek, Joost N.H.; Van Leeuwen, Piet W.N.M.; Wever, Ron; Schoemaker, Hans E.; Tetrahedron Asymmetry; vol. 12; nb. 7; (2001); p. 1025 - 1034 View in Reaxys

Br N

Rx-ID: 8816814 View in Reaxys 335/824 Yield

Conditions & References With copper(l) iodide in tetrahydrofuran, diethyl ether, Time= 3h, T= 0 °C , Grignard reaction De Luca, Lidia; Giacomelli, Giampaolo; Porcheddu, Andrea; Organic Letters; vol. 3; nb. 10; (2001); p. 1519 - 1521 View in Reaxys

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O Si

Rx-ID: 8824457 View in Reaxys 336/824 Yield

Conditions & References

92 %

With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 1.5h, T= 20 °C Ooi; Ooi, Takashi; Sugimoto; Sugimoto, Hayato; Maruoka; Maruoka, Keiji; Heterocycles; vol. 54; nb. 2; (2001); p. 593 596 View in Reaxys O

Rx-ID: 8826418 View in Reaxys 337/824 Yield

Conditions & References

88 %

With titanium(II) diisopropoxide in tetrahydrofuran, Time= 12h, T= 25 °C Eisch, John J.; Gitua, John N.; Otieno, Peter O.; Shi, Xian; Journal of Organometallic Chemistry; vol. 624; nb. 1-2; (2001); p. 229 - 238 View in Reaxys

O OH

H (v2)

H O

Rx-ID: 10306736 View in Reaxys 338/824 Yield

Conditions & References With (R)-aromatic alcohol dehydrogenase (Lactobacillus kefir), (S)-aromatic alcohol dehydrogenase (Thermoanaerobium sp.), (S)-(-)-2,2-dimethyl-5,5-diphenyl-4-isopropyl-1,3-oxazolidine in toluene, Product distribution, Enzyme kinetics, Kinetics, Further Variations: Solvents, Reagents, Catalysts Abato; Seto; Journal of the American Chemical Society; vol. 123; nb. 37; (2001); p. 9206 - 9207 View in Reaxys With (R)-aromatic alcohol dehydrogenase (Lactobacillus kefir), (S)-aromatic alcohol dehydrogenase (Thermoanaerobium sp.), (R)-4-isopropyl-2,2-dimethyl-oxazolidine in toluene, Product distribution, Enzyme kinetics, Kinetics, Further Variations: Solvents, Reagents, Catalysts Abato; Seto; Journal of the American Chemical Society; vol. 123; nb. 37; (2001); p. 9206 - 9207 View in Reaxys O

diacetylmeso-tartaric acid HO

Rx-ID: 15351690 View in Reaxys 339/824 Yield

Conditions & References Reaction Steps: 2

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1: N-methylmorpholine / tetrahydrofuran / 1 h / 20 °C 2: CuI / tetrahydrofuran; diethyl ether / 3 h / 0 °C With 4-methyl-morpholine, copper(l) iodide in tetrahydrofuran, diethyl ether, 2: Grignard reaction De Luca, Lidia; Giacomelli, Giampaolo; Porcheddu, Andrea; Organic Letters; vol. 3; nb. 10; (2001); p. 1519 - 1521 View in Reaxys

O O

Rx-ID: 4470990 View in Reaxys 340/824 Yield 66 %

Conditions & References With samarium, mercury dichloride in tetrahydrofuran, water, T= 20 °C , Desulfonylation Guo, Hongyun; Zhang, Yongmin; Synthetic Communications; vol. 30; nb. 14; (2000); p. 2559 - 2564 View in Reaxys

56 %

With samarium, titanium tetrachloride in tetrahydrofuran, Time= 2h, Heating Wang, Junquan; Zhang, Yongmin; Synthetic Communications; vol. 26; nb. 10; (1996); p. 1931 - 1934 View in Reaxys O

Rx-ID: 8556113 View in Reaxys 341/824 Yield

Conditions & References With bis(dibenzylideneacetone)-palladium(0) in acetonitrile, Time= 20h, T= 50 °C , Ring cleavage, Title compound not separated from byproducts Okumoto, Hiroshi; Jinnai, Takamitsu; Shimizu, Hiroyuki; Harada, Yoshinori; Mishima, Hideki; Suzuki, Akira; Synlett; nb. 5; (2000); p. 629 - 630 View in Reaxys O

Rx-ID: 8556900 View in Reaxys 342/824 Yield 93 % Chromat.

Conditions & References With tetra(n-butyl)ammonium hydrogensulfate, hypochloric acid in dichloromethane, chlorobenzene, Time= 0.5h, T= 20 °C , pH= 9.0 - 9.3, η-scission Dailey, Jennifer I.; Hays, Ryan S.; Lee, Hua; Mitchell, Randall M.; Ries, Jennifer J.; Landolt, Robert G.; Husmann, Hollie H.; Lockridge, Joseph B.; Hendrickson, William H.; Journal of Organic Chemistry; vol. 65; nb. 8; (2000); p. 2568 - 2571 View in Reaxys

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Rx-ID: 856724 View in Reaxys 343/824 Yield

Conditions & References

78 %

With bis(cyclopentadienyl)titanium dichloride, isopropylmagnesium bromide in tetrahydrofuran, diethyl ether, Time= 4h, Ambient temperature Yu, Yongping; Zhang, Yongmin; Synthetic Communications; vol. 29; nb. 2; (1999); p. 243 - 247 View in Reaxys With hydrogenchloride Rupe; Pieper; Helvetica Chimica Acta; vol. 12; (1929); p. 645 View in Reaxys bei der Destillation mit auf 150grad erhitztem Wasserdampf Rupe; Pieper; Helvetica Chimica Acta; vol. 12; (1929); p. 645 View in Reaxys With hydrogenchloride in ethanol Bestmann,H.J. et al.; Chemische Berichte; vol. 103; (1970); p. 2794 - 2801 View in Reaxys T= 150 °C , bei der Destillation mit ueberhitztem Wasserdampf Rupe; Pieper; Helvetica Chimica Acta; vol. 12; (1929); p. 645 View in Reaxys O

Rx-ID: 2035194 View in Reaxys 344/824 Yield

Conditions & References

87 %

With indium, water, Time= 3h, ultrasound Ranu, Brindaban C.; Dutta, Pinak; Sarkar, Arunkanti; Journal of the Chemical Society - Perkin Transactions 1; nb. 9; (1999); p. 1139 - 1140 View in Reaxys

70 % Spectr.

With sulfuric acid, sodium iodide in tetrahydrofuran, water, Time= 2h, Ambient temperature Gemal, A.L.; Luche, J.L.; Tetrahedron Letters; vol. 21; (1980); p. 3195 - 3198 View in Reaxys O

Rx-ID: 2068079 View in Reaxys 345/824 Yield 94 %

Conditions & References With sodium perborate in acetic acid, Time= 5h, T= 50 - 60 °C McKillop, Alexander; Tarbin, Jonathan A.; Tetrahedron; vol. 43; nb. 8; (1987); p. 1753 - 1758

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View in Reaxys 98 % Chromat.

With air, water, palladium diacetate, tin(ll) chloride in N,N-dimethyl-formamide, Time= 24h, Hydrolysis Mino, Takashi; Hirota, Tatsuya; Fujita, Noriko; Yamashita, Masakazu; Synthesis; nb. 12; (1999); p. 2024 - 2026 View in Reaxys

N N

Rx-ID: 4425744 View in Reaxys 346/824 Yield

Conditions & References

100 %

With 2-phenyl-1,2-benzoisoselenazol-3(2H)-one, dihydrogen peroxide in methanol, water, Time= 1.5h, T= 65 °C Mlochowski, Jacek; Giurg, Miroslaw; Kubicz, Elzbieta; Said, Samy B.; Synthetic Communications; vol. 26; nb. 2; (1996); p. 291 - 300 View in Reaxys

93 %

With ammonium cerium(IV) nitrate in water, acetonitrile, Time= 16h, T= 20 °C , Oxidation Giurg, Miroslaw; Mlochowski, Jacek; Synthetic Communications; vol. 29; nb. 24; (1999); p. 4307 - 4313 View in Reaxys O

O HO

Rx-ID: 5088933 View in Reaxys 347/824 Yield

Conditions & References With n-butyllithium, <Rh(dppe)COD>ClO4, 1.) THF, hexane, 60 deg C, 7 h, 2.) THF, hexane, Yield given, Multistep reaction. Yields of byproduct given Gazzard, Lewis J.; Motherwell, William B.; Sandham, David A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1999); p. 979 - 993 View in Reaxys O HO

O O

Rx-ID: 5093329 View in Reaxys 348/824 Yield 9 %, 91 %

Conditions & References With dihydrogen peroxide, methyltrioxorhenium(VII), sodium bromide in acetic acid, Time= 10h, Ambient temperature Espenson; Zhu; Zauche; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1191 - 1196 View in Reaxys

Rx-ID: 5094028 View in Reaxys 349/824

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Yield

Conditions & References

49 %

With dihydrogen peroxide, methyltrioxorhenium(VII), sodium bromide in acetic acid, Time= 12h, Ambient temperature Espenson; Zhu; Zauche; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1191 - 1196 View in Reaxys O

O HO

Rx-ID: 5094261 View in Reaxys 350/824 Yield

Conditions & References With n-butyllithium, benzyl bromide, <Rh(dppe)COD>ClO4, 1.) THF, hexane, 60 deg C, 7 h, 2.) THF, hexane, Yield given, Multistep reaction. Yields of byproduct given Gazzard, Lewis J.; Motherwell, William B.; Sandham, David A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1999); p. 979 - 993 View in Reaxys O

Rx-ID: 5094903 View in Reaxys 351/824 Yield

Conditions & References

73 %

O HO

Rx-ID: 5100146 View in Reaxys 352/824 Yield

O O

Rx-ID: 5104313 View in Reaxys 353/824 Yield 9 %, 91 %

Conditions & References With dihydrogen peroxide, methyltrioxorhenium(VII), sodium bromide, Time= 10h, Ambient temperature Espenson; Zhu; Zauche; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1191 - 1196

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View in Reaxys O

O HO

Rx-ID: 5107412 View in Reaxys 354/824 Yield

O HO I

Rx-ID: 5132678 View in Reaxys 355/824 Yield

O O

Rx-ID: 5136643 View in Reaxys 356/824 Yield

Conditions & References

6 % Chromat., 11 % Chromat., 31 % Chromat., 1 % Chromat., 51 % Chromat.

With potassium hydroxide, hydrogen, 10% platinum on carbon in 2,2,4-trimethylpentane, water, Time= 0.283333h, T= 50 °C , p= 760Torr , Product distribution Perosa, Alvise; Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 64; nb. 11; (1999); p. 3934 - 3939 View in Reaxys

O Cl

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O O

Rx-ID: 5136644 View in Reaxys 357/824 Yield

Conditions & References

85 % Chromat., 1 % Chromat., 2 % Chromat., 12 % Chromat.

With potassium hydroxide, hydrogen, 10% platinum on carbon in 2,2,4-trimethylpentane, water, Time= 6h, T= 50 °C , p= 760Torr , other reagent, reaction time, various KOH concentrations, pH effect, Product distribution Perosa, Alvise; Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 64; nb. 11; (1999); p. 3934 - 3939 View in Reaxys

Rx-ID: 5196737 View in Reaxys 358/824 Yield

Conditions & References

97 %

With dihydrogen peroxide, bromine in dichloromethane, water, Time= 24h, T= 20 °C Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 261 - 269 View in Reaxys

81 % Spectr.

H N

O HO

Rx-ID: 5198345 View in Reaxys 359/824 Yield

Conditions & References

64 %, 25 %

With S4N4*SbCl5 in toluene, Time= 1h, T= 60 °C , Rearrangement, Beckmann rearrangement Kim, Kil Joong; Kim, Kyongtae; Heterocycles; vol. 50; nb. 1; (1999); p. 147 - 157 View in Reaxys

O OH H

H HO

O OH

Rx-ID: 5200370 View in Reaxys 360/824

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Yield

Conditions & References With Coprinus peroxidase (CiP), 2-methoxy-phenol in water, Time= 20h, T= 72 °C , phosphate buffer pH 7.0; enzyme-catalyzed kinetic resolution of chiral hydroperoxides in the presence and absence of guaiacol; selectivity; enantiomeric excess; CiPcatalyzed disproportionation; radical formation; mechanism; CiP-catalyzed sulfoxidation, Product distribution Adam, Waldemar; Mock-Knoblauch, Cordula; Saha-Moeller, Chantu R.; Journal of Organic Chemistry; vol. 64; nb. 13; (1999); p. 4834 - 4839 View in Reaxys O O

HO O

Rx-ID: 5214949 View in Reaxys 361/824 Yield

Conditions & References With trimagnesium phosphate, Time= 1.33333h, T= 499.85 °C , aldol condensation, dehydration, hydrogenation, Product distribution, Further Variations: Catalysts, Temperatures, Reaction partners Aramendia, Maria Angeles; Borau, Victoriano; Jimenez, Cesar; Marinas, Jose Maria; Romero, Francisco Jose; Journal of Catalysis; vol. 183; nb. 1; (1999); p. 119 - 127 View in Reaxys O O

Rx-ID: 5217414 View in Reaxys 362/824 Yield 75 %, 18 %

Conditions & References With N,N,N,N,N,N-hexamethylphosphoric triamide, dibutyltin, Dibutyldifluorotin in tetrahydrofuran, T= 20 °C , Reduction Moriuchi-Kawakami, Takayo; Matsuda, Haruo; Shibata, Ikuya; Miyatake, Masato; Suwa, Toshihiro; Baba, Akio; Bulletin of the Chemical Society of Japan; vol. 72; nb. 3; (1999); p. 465 - 470 View in Reaxys O

bis<chloro(η3-1,3-diphenylallyl)palladium>

HI, I2 O

Rx-ID: 16439508 View in Reaxys 363/824 Yield

Conditions & References Reaction Steps: 2 1: 76 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 2 h 2: 1.) n-BuLi / 1.) <Rh(dppe)COD>ClO4 / 1.) THF, hexane, 60 deg C, 7 h, 2.) THF, hexane With n-butyllithium, <Rh(dppe)COD>ClO4 in tetrahydrofuran Gazzard, Lewis J.; Motherwell, William B.; Sandham, David A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1999); p. 979 - 993 View in Reaxys Reaction Steps: 2 1: 76 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 2 h 2: 1.) n-BuLi, 2.) benzyl bromide / 1.) <Rh(dppe)COD>ClO4 / 1.) THF, hexane, 60 deg C, 7 h, 2.) THF, hexane With n-butyllithium, benzyl bromide, <Rh(dppe)COD>ClO4 in tetrahydrofuran Gazzard, Lewis J.; Motherwell, William B.; Sandham, David A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1999); p. 979 - 993

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View in Reaxys Reaction Steps: 2 1: 76 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 2 h 2: 1.) n-BuLi / 1.) <Rh(dppe)COD>ClO4 / 1.) THF, hexane, 60 deg C, 7 h, 2.) THF, hexane With n-butyllithium, <Rh(dppe)COD>ClO4 in tetrahydrofuran Gazzard, Lewis J.; Motherwell, William B.; Sandham, David A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1999); p. 979 - 993 View in Reaxys Reaction Steps: 2 1: 76 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 2 h 2: 1.) n-BuLi / 1.) <Rh(dppe)COD>ClO4 / 1.) THF, hexane, 60 deg C, 7 h, 2.) THF, hexane With n-butyllithium, <Rh(dppe)COD>ClO4 in tetrahydrofuran Gazzard, Lewis J.; Motherwell, William B.; Sandham, David A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1999); p. 979 - 993 View in Reaxys Reaction Steps: 2 1: 76 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 2 h 2: 1.) n-BuLi / 1.) <Rh(dppe)COD>ClO4 / 1.) THF, hexane, 60 deg C, 7 h, 2.) THF, hexane With n-butyllithium, <Rh(dppe)COD>ClO4 in tetrahydrofuran Gazzard, Lewis J.; Motherwell, William B.; Sandham, David A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1999); p. 979 - 993 View in Reaxys

N S

Rx-ID: 4099247 View in Reaxys 364/824 Yield 19 %

Conditions & References With ethylaluminum dichloride in dichloromethane, Time= 12h, Ambient temperature Kataoka; Iwama; Tetrahedron Letters; vol. 36; nb. 2; (1995); p. 245 - 248 View in Reaxys

19 %

With ethylaluminum dichloride in hexane, dichloromethane, Time= 12h, Ambient temperature Iwama, Tetsuo; Ogawa, Miyoko; Kataoka, Tadashi; Muraoka, Osamu; Tanabe, Genzoh; Tetrahedron; vol. 54; nb. 31; (1998); p. 8941 - 8974 View in Reaxys O

Rx-ID: 4853775 View in Reaxys 365/824 Yield 43 %

Conditions & References With 2-Amino-4-methylpyridine, rhodium(III) chloride, triphenylphosphine in benzene, Time= 12h, T= 130 °C Jun, Chul-Ho; Huh, Chan-Woo; Na, Sang-Jin; Angewandte Chemie - International Edition; vol. 37; nb. 1-2; (1998); p. 145 147 View in Reaxys

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O O

Rx-ID: 4867348 View in Reaxys 366/824 Yield

Conditions & References

36 %, 16 %

With sodium hydride in N,N-dimethyl-formamide, Time= 24h, T= 70 - 80 Â°C Nymann, Kirsten; Svendsen, John S.; Acta Chemica Scandinavica; vol. 52; nb. 3; (1998); p. 338 - 349 View in Reaxys O

Br O

Rx-ID: 4881262 View in Reaxys 367/824 Yield

Conditions & References With GeI2 in tetrahydrofuran, Time= 6h, Ambient temperature, Yield given. Yields of byproduct given Kagoshima, Hirotaka; Hashimoto, Yukihiko; Oguro, Dai; Saigo, Kazuhiko; Journal of Organic Chemistry; vol. 63; nb. 3; (1998); p. 691 - 697 View in Reaxys O

Rx-ID: 4885908 View in Reaxys 368/824 Yield

Conditions & References

0 %, 0 %, 75 %

With germaniumtetrachloride, benzaldehyde in tetrahydrofuran, 1.) room temp., 72 h, 2.) reflux, 6 h Kagoshima, Hirotaka; Hashimoto, Yukihiko; Oguro, Dai; Saigo, Kazuhiko; Journal of Organic Chemistry; vol. 63; nb. 3; (1998); p. 691 - 697 View in Reaxys O

O P

O O

Rx-ID: 5011411 View in Reaxys 369/824 Yield

Conditions & References With sodium hydroxide, 1.) toluene, -78 deg C, 10 min, 2.) H2O, DME, room temperature, 1 h., Yield given. Multistep reaction

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Maeda, Hatsuo; Takahashi, Kenji; Ohmori, Hidenobu; Tetrahedron; vol. 54; nb. 40; (1998); p. 12233 - 12242 View in Reaxys O O

O P

Rx-ID: 5011420 View in Reaxys 370/824 Yield

Conditions & References With sodium hydroxide, 1.) toluene, -78 deg C, 10 min, 2.) DME, H2O, room temperature, 1 h., Yield given. Multistep reaction Maeda, Hatsuo; Takahashi, Kenji; Ohmori, Hidenobu; Tetrahedron; vol. 54; nb. 40; (1998); p. 12233 - 12242 View in Reaxys

Si N

Rx-ID: 5021793 View in Reaxys 371/824 Yield

Conditions & References With water, silica gel, Yield given Ortiz-Marciales, Margarita; Tirado, Liz M.; Colon, Roberto; Ufret, Maria L.; Figueroa, Ruth; Lebron, Marisabel; DeJesus, Melvin; Martinez, Johanna; Malave, Tania; Synthetic Communications; vol. 28; nb. 21; (1998); p. 4067 - 4075 View in Reaxys

O H 2N

N N

Rx-ID: 5055077 View in Reaxys 372/824 Yield

Conditions & References

47 %

With iodine, mercury(II) oxide in dichloromethane, Time= 1h, T= 20 Â°C , Oxidation Orito, Kazuhiko; Hatakeyama, Takahiro; Takeo, Mitsuhiro; Uchiito, Shiho; Tokuda, Masao; Suginome, Hiroshi; Tetrahedron; vol. 54; nb. 29; (1998); p. 8403 - 8410 View in Reaxys

O F

HO F

O F

F O

Rx-ID: 5091200 View in Reaxys 373/824

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Yield

Conditions & References

3 %, 9 %, 0.7 %

With 2,6-dimethylpyridine, Time= 3h, T= 20 °C , Irradiation Usui, Satoshi; Matsumoto, Takeshi; Ohkubo, Katsutoshi; Tetrahedron Letters; vol. 39; nb. 52; (1998); p. 9755 - 9758 View in Reaxys

HO F

O F

F O

Rx-ID: 5091201 View in Reaxys 374/824 Yield

Conditions & References

3 %, 9 %, With 2,6-dimethylpyridine, Time= 3h, T= 20 °C , Irradiation 85 %, 0.7 % Usui, Satoshi; Matsumoto, Takeshi; Ohkubo, Katsutoshi; Tetrahedron Letters; vol. 39; nb. 52; (1998); p. 9755 - 9758 View in Reaxys O Cl Br

Rx-ID: 5098880 View in Reaxys 375/824 Yield

Conditions & References With naphthalene, lithium, manganese(ll) chloride, 1.) Et2O, 20 deg C, 4 h; 2.) Et2O, 20 h, Yield given, Multistep reaction Hojo, Makoto; Yoshizawa, Junji; Funahashi, Yoshihiro; Okada, Ryo; Nakamura, Shin-Ya; Tateiwa, Jun-Ichi; Hosomi, Akira; Heterocycles; vol. 49; nb. 1; (1998); p. 85 - 88 View in Reaxys

O F

F O

Rx-ID: 5111189 View in Reaxys 376/824 Yield 9%

Conditions & References With 2,6-dimethylpyridine, 2,2,2-trifluoroethanol, Irradiation Usui, Satoshi; Matsumoto, Takeshi; Ohkubo, Katsutoshi; Tetrahedron Letters; vol. 39; nb. 52; (1998); p. 9755 - 9758 View in Reaxys

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tin tetrachloride

bis<chloro(η3-1,3-diphenylallyl)palladium>

Rx-ID: 16554112 View in Reaxys 377/824 Yield

Conditions & References Reaction Steps: 2 1: AlCl3 2: TFE, 2,6-lutidine / Irradiation With 2,6-dimethylpyridine, aluminium trichloride, 2,2,2-trifluoroethanol Usui, Satoshi; Matsumoto, Takeshi; Ohkubo, Katsutoshi; Tetrahedron Letters; vol. 39; nb. 52; (1998); p. 9755 - 9758 View in Reaxys

4-isopropyl-phenyl magnesium halide O

/PCCWF195-1820/

Rx-ID: 16709231 View in Reaxys 378/824 Yield

Conditions & References Reaction Steps: 2 1: CuBr / tetrahydrofuran / -78 - 0 °C 2: H2O, silica gel With water, silica gel, copper(I) bromide in tetrahydrofuran Ortiz-Marciales, Margarita; Tirado, Liz M.; Colon, Roberto; Ufret, Maria L.; Figueroa, Ruth; Lebron, Marisabel; DeJesus, Melvin; Martinez, Johanna; Malave, Tania; Synthetic Communications; vol. 28; nb. 21; (1998); p. 4067 - 4075 View in Reaxys O O

Rx-ID: 660094 View in Reaxys 379/824 Yield 70 %

Conditions & References With HY-Zeolite, Time= 12h, T= 250 °C , other catalyst: HZSM-5 Sreekumar; Padmakumar, Raghavakaimal; Synthetic Communications; vol. 27; nb. 5; (1997); p. 777 - 780 View in Reaxys With aluminium trichloride Patent; I.G. Farbenind.; DE646702; (1933); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 24; p. 179 View in Reaxys With aluminium trichloride, iron(III) chloride Riddell; Noller; Journal of the American Chemical Society; vol. 54; (1932); p. 290,291, 292

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View in Reaxys O

Rx-ID: 4605447 View in Reaxys 380/824 Yield

Conditions & References With hydrogen, Rh-PEVV in water, Time= 2h, T= 40 °C , p= 31052.5Torr , other time; catalytic hydroformylation of olefins in biphastic reaction conditions; turnover frequency; conversion, selectivity, Product distribution Chen, Jinhua; Alper, Howard; Journal of the American Chemical Society; vol. 119; nb. 5; (1997); p. 893 - 895 View in Reaxys O H

Rx-ID: 4625574 View in Reaxys 381/824 Yield

Conditions & References

92 %

With 3-methylpyridin-2-ylamine, Wilkinson's catalyst in benzene, Time= 24h, T= 150 °C Jun, Chul-Ho; Lee, Hyuk; Hong, Jun-Bae; Journal of Organic Chemistry; vol. 62; nb. 5; (1997); p. 1200 - 1201 View in Reaxys

Rx-ID: 4676307 View in Reaxys 382/824 Yield

Conditions & References

99 %

With water, PtCl4-CO in tetrahydrofuran, Time= 2h, T= 80 °C , p= 1034.3Torr Baidossi, Wael; Lahav, Michal; Blum, Jochanan; Journal of Organic Chemistry; vol. 62; nb. 3; (1997); p. 669 - 672 View in Reaxys

O HO

O O

Rx-ID: 4677405 View in Reaxys 383/824 Yield 70 %

Conditions & References T= 650 °C , p= 0.01Torr Aitken, R. Alan; Thomas, Andrew W.; Synlett; vol. 1997; nb. 3; (1997); p. 293 - 294 View in Reaxys

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HO O

Rx-ID: 4690560 View in Reaxys 384/824 Yield

Conditions & References With water, Aliquat 336, platinum(IV) chloride in various solvent(s), Time= 5h, T= 110 °C , p= 1034.3Torr , Yield given. Yields of byproduct given. Title compound not separated from byproducts Baidossi, Wael; Lahav, Michal; Blum, Jochanan; Journal of Organic Chemistry; vol. 62; nb. 3; (1997); p. 669 - 672 View in Reaxys O

Rx-ID: 4713500 View in Reaxys 385/824 Yield

Conditions & References

100 %

O P O

Rx-ID: 4781833 View in Reaxys 386/824 Yield

Conditions & References With lithium aluminium tetrahydride, n-butyllithium, 1) THF, -78 deg C, 1 h, 2) THF, -78 deg C -> -5 deg C, 30 min, 3) THF, -5 deg C -> room temperature, 30 min, Yield given. Multistep reaction Jang, Won Bum; Shin, Won Suk; Hong, Jong Eun; Lee, Shi Yong; Oh, Dong Young; Synthetic Communications; vol. 27; nb. 19; (1997); p. 3333 - 3339 View in Reaxys

HO HO

Rx-ID: 4934015 View in Reaxys 387/824 Yield

Conditions & References With tert.-butylhydroperoxide, aluminum tri-tert-butoxide in benzene, Time= 84h, T= 20 - 70 °C , Mechanism, Product distribution

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Stepovik; Dodonov; Zaburdaeva; Russian Journal of General Chemistry; vol. 67; nb. 1; (1997); p. 111 - 115 View in Reaxys O

Rx-ID: 5070763 View in Reaxys 388/824 Yield

Conditions & References With Lithium dimsyl in dimethyl sulfoxide, T= 18 °C , fragmentation, Kinetics, Further Variations: Temperatures Moosavi, Sayid M.; Beddoes, Roy S.; Watt, C. Ian F.; Journal of the Chemical Society. Perkin Transactions 2; nb. 8; (1997); p. 1585 - 1596 View in Reaxys O

Rx-ID: 5070764 View in Reaxys 389/824 Yield

EtMgX

Rx-ID: 5931102 View in Reaxys 390/824 Yield

Conditions & References in ethanol Musso, David L.; Mehta, Nariman B.; Soroko, Francis E.; Bioorganic and Medicinal Chemistry Letters; vol. 7; nb. 1; (1997); p. 1 - 6 View in Reaxys OH O

copper oxide-chromium oxide catalyst O

/PCCWF195-1820/

Rx-ID: 17411628 View in Reaxys 391/824 Yield

Conditions & References Reaction Steps: 2 1: 93 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 15 min; 2.) warm up to RT, 1 h

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2: 70 percent / 650 °C / 0.01 Torr With lithium diisopropyl amide in tetrahydrofuran Aitken, R. Alan; Thomas, Andrew W.; Synlett; vol. 1997; nb. 3; (1997); p. 293 - 294 View in Reaxys O

metaphosphoric acid HO

/PCCWF195-1820/

Rx-ID: 17428991 View in Reaxys 392/824 Yield

Conditions & References Reaction Steps: 2 1: 1.) SOCl2, 2.) NH4OH, 3.) SOCl2 / 2.) dioxane, 3.) reflux 2: ethanol With ammonium hydroxide, thionyl chloride in ethanol Musso, David L.; Mehta, Nariman B.; Soroko, Francis E.; Bioorganic and Medicinal Chemistry Letters; vol. 7; nb. 1; (1997); p. 1 - 6 View in Reaxys

O HO

Rx-ID: 4423833 View in Reaxys 393/824 Yield

Conditions & References

3 %, 79 %, 3%

With methyltrioxorhenium(VII) in benzene, Time= 48h, Ambient temperature Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 61; nb. 1; (1996); p. 324 - 328 View in Reaxys O O

Rx-ID: 4470441 View in Reaxys 394/824 Yield 55 %

Conditions & References With dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc, zinc in ethanol, Time= 18h, Heating Yadav, K. Mallik; Suresh, Joghee R.; Patro, Balaram; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar; Tetrahedron; vol. 52; nb. 13; (1996); p. 4679 - 4686 View in Reaxys

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O O

O O P O

Rx-ID: 4472515 View in Reaxys 395/824 Yield

Conditions & References With lithium aluminium tetrahydride, sulfuric acid, sodium hydride, 1.) THF, room temperature, 1 h, 2.) THF, room temperature, 10 min, 3.) H2O, Yield given. Multistep reaction Hong, Jong Eoun; Shin, Won Suk; Jang, Won Bum; Oh, Dong Young; Journal of Organic Chemistry; vol. 61; nb. 6; (1996); p. 2199 - 2201 View in Reaxys OH

Rx-ID: 4485363 View in Reaxys 396/824 Yield

Conditions & References With aluminium tris(2,6-diphenylphenoxide), n-butyllithium, diisobutylaluminium hydride, 1) toluene, -78 deg C; 2) toluene, THF, hexane, -78 deg C --> rt, Yield given. Multistep reaction. Yields of byproduct given Saito, Susumu; Yamamoto, Hisashi; Journal of Organic Chemistry; vol. 61; nb. 9; (1996); p. 2928 - 2929 View in Reaxys

H N

N NH

Rx-ID: 4503225 View in Reaxys 397/824 Yield

Conditions & References

84 % in (2)H8-toluene, Time= 7h, T= 150 Â°C , Title compound not separated from byproducts Spectr., 7 % Spectr., 9 % Kawashima, Takayuki; Yamashita, Naoko; Okazaki, Renji; Chemistry Letters; nb. 3; (1996); p. 213 - 214 Spectr. View in Reaxys

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O O

Rx-ID: 4509724 View in Reaxys 398/824 Yield

Conditions & References With hydrogen, Aliquat 336, 10 wt. % palladium on activated carbon in 2,2,4-trimethylpentane, T= 50 °C , Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Gazzetta Chimica Italiana; vol. 126; nb. 6; (1996); p. 317 - 328 View in Reaxys O

O Cl

Rx-ID: 4517720 View in Reaxys 399/824 Yield

Conditions & References

2 % Chromat., 98 % Chromat.

With potassium hydroxide, hydrogen, Aliquat 336, 10 wt. % palladium on activated carbon in 2,2,4-trimethylpentane, Time= 20h, T= 50 °C , Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Gazzetta Chimica Italiana; vol. 126; nb. 6; (1996); p. 317 - 328 View in Reaxys

O S

Rx-ID: 4519307 View in Reaxys 400/824 Yield

Conditions & References

86.9 % Chromat., 79.1 % Chromat.

With 2,2'-azobis(isobutyronitrile) in benzene, Time= 48h, T= 61 °C Li, Xianfeng; Chen, Jian J.; Tanner, Dennis D.; Journal of Organic Chemistry; vol. 61; nb. 13; (1996); p. 4314 - 4318 View in Reaxys With 2,2'-azobis(isobutyronitrile) in benzene, Time= 48h, T= 61 °C , Product distribution, Mechanism Li, Xianfeng; Chen, Jian J.; Tanner, Dennis D.; Journal of Organic Chemistry; vol. 61; nb. 13; (1996); p. 4314 - 4318 View in Reaxys O

O I

Rx-ID: 4574852 View in Reaxys 401/824 Yield

Conditions & References With N,N,N,N,N,N-hexamethylphosphoric triamide, sec.-butyllithium, samarium(III) trifluoromethanesulfonate, 1.) THF, cyclohexane, room temperature, 1 h, 2.) THF, cyclohexane, room temperature, 1 h, Yield given. Multistep reaction Fukuzawa, Shin-Ichi; Mutoh, Keisuke; Tsuchimoto, Teruhisa; Hiyama, Tamejiro; Journal of Organic Chemistry; vol. 61; nb. 16; (1996); p. 5400 - 5405

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View in Reaxys O

Rx-ID: 716324 View in Reaxys 402/824 Yield

Conditions & References With yttrium(III) chloride, Triethylgermyl-natrium, multistep reaction; other ketones, var. solvents and additives, var. catalyst systems, Product distribution Yokoyama, Yasuo; Mochida, Kunio; Journal of Organometallic Chemistry; vol. 499; nb. 1-2; (1995); p. C4 - C6 View in Reaxys With potassium carbonate, T= 100 °C Nef; Justus Liebigs Annalen der Chemie; vol. 310; (1900); p. 323 View in Reaxys With yttrium(III) chloride, Triethylgermyl-natrium, 1.) THF, HMPA, RT, 1 h, 2.) THF, HMPA, -78 deg C, 1.5 h, Yield given. Multistep reaction Yokoyama, Yasuo; Mochida, Kunio; Journal of Organometallic Chemistry; vol. 499; nb. 1-2; (1995); p. C4 - C6 View in Reaxys With ytterbium(III) chloride, Triethylgermyl-natrium, 1.) Et2O, HMPA, 2.) Et2O, HMPA, -78 deg C, Yield given. Multistep reaction. Yields of byproduct given Yokoyama, Yasuo; Mochida, Kunio; Journal of Organometallic Chemistry; vol. 499; nb. 1-2; (1995); p. C4 - C6 View in Reaxys O

O O Ga

Rx-ID: 4084627 View in Reaxys 403/824 Yield

Conditions & References With lithium phenylacetylide, 1.) 0 deg C, THF/hexane, 30 min 2.) 0 deg C r.t., THF/hexane, 1 h, Yield given. Multistep reaction. Yields of byproduct given Han, Ying; Fang, Lei; Tao, Wen-Tian; Huang, Yao-Zeng; Tetrahedron Letters; vol. 36; nb. 8; (1995); p. 1287 - 1290 View in Reaxys O

O O

Li Cl

Rx-ID: 4084807 View in Reaxys 404/824 Yield

Conditions & References With triethyl gallium, 1.) 0 deg C, THF/hexane, 30 min 2.) 0 deg C r.t., THF/hexane, 1 h, Yield given. Multistep reaction. Yields of byproduct given Han, Ying; Fang, Lei; Tao, Wen-Tian; Huang, Yao-Zeng; Tetrahedron Letters; vol. 36; nb. 8; (1995); p. 1287 - 1290 View in Reaxys

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O O

Rx-ID: 4149432 View in Reaxys 405/824 Yield

Conditions & References

72 %, 25 %, With potassium hydroxide, hydrogen, Aliquat 336, 10 wt. % palladium on activated carbon in pentane, Time= 0.166667h, T= 3% 30 Â°C , various solvents, time, temp.; also in the absence of Aliquat 336; further aromatic ketones, Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2430 2435 View in Reaxys

O HO

Rx-ID: 4154389 View in Reaxys 406/824 Yield

Conditions & References

10 %, 63 %

in diethyl ether, Time= 1h, Ambient temperature Kashima, Choji; Kita, Isanobu; Takahashi, Katsumi; Hosomi, Akira; Journal of Heterocyclic Chemistry; vol. 32; nb. 1; (1995); p. 25 - 28 View in Reaxys

O HO

Rx-ID: 4154391 View in Reaxys 407/824 Yield 12 %, 65 %

Conditions & References in diethyl ether, Time= 1h, Ambient temperature Kashima, Choji; Kita, Isanobu; Takahashi, Katsumi; Hosomi, Akira; Journal of Heterocyclic Chemistry; vol. 32; nb. 1; (1995); p. 25 - 28 View in Reaxys

O O

N N N

Rx-ID: 4446112 View in Reaxys 408/824 Yield

Conditions & References With hydrogenchloride in tetrahydrofuran, Ambient temperature, Yield given

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Katritzky, Alan R.; Lang, Hengyuan; Wang, Zuoquan; Zhang, Zhongxing; Song, Huimin; Journal of Organic Chemistry; vol. 60; nb. 23; (1995); p. 7619 - 7624 View in Reaxys O

O O

/PBNYG055--511/ Cl

Rx-ID: 5931110 View in Reaxys 409/824 Yield

Conditions & References

46 %, 37 %

in tetrahydrofuran, hexane, Time= 1h, T= 0 °C , to room temperature Han, Ying; Fang, Lei; Tao, Wen-Tian; Huang, Yao-Zeng; Tetrahedron Letters; vol. 36; nb. 8; (1995); p. 1287 - 1290 View in Reaxys

Br–

+Mg

Rx-ID: 6682937 View in Reaxys 410/824 Yield

Conditions & References

4 %, 67 %

in diethyl ether, Time= 1h, Ambient temperature Kashima, Choji; Kita, Isanobu; Takahashi, Katsumi; Hosomi, Akira; Journal of Heterocyclic Chemistry; vol. 32; nb. 1; (1995); p. 25 - 28 View in Reaxys O

hydrogen

2-hydroxy-2-phenyl-butyraldehyde-oxime

Rx-ID: 17796269 View in Reaxys 411/824 Yield

Conditions & References Reaction Steps: 3 1: 85 percent / toluene / 4 h / Heating 2: 85 percent / n-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 2.) -78 deg C, 2 min 3: aq. HCl / tetrahydrofuran / Ambient temperature With hydrogenchloride, n-butyllithium in tetrahydrofuran, cyclohexane, toluene Katritzky, Alan R.; Lang, Hengyuan; Wang, Zuoquan; Zhang, Zhongxing; Song, Huimin; Journal of Organic Chemistry; vol. 60; nb. 23; (1995); p. 7619 - 7624 View in Reaxys O

sodium cyanate

2-hydroxy-2-phenyl-butyraldehyde-oxime

Rx-ID: 17803737 View in Reaxys 412/824 Yield

Conditions & References Reaction Steps: 3 1: 70 percent / H2SO4 / ethanol; tetrahydrofuran / 1.) r.t., 3 h, 2.) reflux, 3 h

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2: 85 percent / n-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 2.) -78 deg C, 2 min 3: aq. HCl / tetrahydrofuran / Ambient temperature With hydrogenchloride, n-butyllithium, sulfuric acid in tetrahydrofuran, ethanol, cyclohexane Katritzky, Alan R.; Lang, Hengyuan; Wang, Zuoquan; Zhang, Zhongxing; Song, Huimin; Journal of Organic Chemistry; vol. 60; nb. 23; (1995); p. 7619 - 7624 View in Reaxys

O O

2-hydroxy-2-phenyl-butyraldehyde-oxime N N N

Rx-ID: 17806509 View in Reaxys 413/824 Yield

Conditions & References Reaction Steps: 2 1: 85 percent / n-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 2.) -78 deg C, 2 min 2: aq. HCl / tetrahydrofuran / Ambient temperature With hydrogenchloride, n-butyllithium in tetrahydrofuran, cyclohexane Katritzky, Alan R.; Lang, Hengyuan; Wang, Zuoquan; Zhang, Zhongxing; Song, Huimin; Journal of Organic Chemistry; vol. 60; nb. 23; (1995); p. 7619 - 7624 View in Reaxys O I

Rx-ID: 1548752 View in Reaxys 414/824 Yield

Conditions & References With silica gel, phosphorous triiodide in dichloromethane, Time= 3h, various reaction times, adsorbents, and the hydroiodination reagent, Product distribution Kropp, Paul J.; Crawford, Scott D.; Journal of Organic Chemistry; vol. 59; nb. 11; (1994); p. 3102 - 3112 View in Reaxys

21 % Chro- With aluminum oxide, phosphorous triiodide, Time= 3h, Title compound not separated from byproducts mat., 66 % Chromat., 3 Kropp, Paul J.; Crawford, Scott D.; Journal of Organic Chemistry; vol. 59; nb. 11; (1994); p. 3102 - 3112 % Chromat. View in Reaxys O O

HO O

Rx-ID: 1985355 View in Reaxys 415/824 Yield 58 %, 25 %

Conditions & References With methyloxirane in water, acetone, Irradiation, pH neutral Sonawane, Harikisan; Bellur, Nanjundiah S.; Kulkarni, Dilip G.; Ayyangar, Nagaraj R.; Tetrahedron; vol. 50; nb. 4; (1994); p. 1243 - 1260 View in Reaxys

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39 %

With sodium hydroxide, methyloxirane, 1.) MeOH, irradiation, pH neutral; 2.) MeOH, reflux, 2 h, Yield given. Multistep reaction Sonawane, Harikisan; Bellur, Nanjundiah S.; Kulkarni, Dilip G.; Ayyangar, Nagaraj R.; Tetrahedron; vol. 50; nb. 4; (1994); p. 1243 - 1260 View in Reaxys

Rx-ID: 2792444 View in Reaxys 416/824 Yield

Conditions & References

84 %

With hydrogenchloride in tetrahydrofuran, Time= 15h, Ambient temperature Jousseaume, Bernard; Vilcot, Nathalie; Ricci, Alfredo; Tiekink, Edward R. T.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 16; (1994); p. 2283 - 2288 View in Reaxys

O S

Rx-ID: 3950774 View in Reaxys 417/824 Yield 96 %

Conditions & References With trimethylsilyl trifluoromethanesulfonate, nitrobenzaldehyde polymer in dichloromethane, Time= 2h, Ambient temperature Ravindranathan, T.; Chavan, Subhash P.; Awachat, Moreshwar M.; Tetrahedron Letters; vol. 35; nb. 47; (1994); p. 8835 8838 View in Reaxys O O

O P O

Rx-ID: 3977736 View in Reaxys 418/824 Yield

Conditions & References With n-butyllithium, water, titanium tetrachloride, Multistep reaction Garossian, Massoud; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 88; nb. 1-4; (1994); p. 279 - 282 View in Reaxys

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O O

Rx-ID: 4003145 View in Reaxys 419/824 Yield 54 %, 3 %

Conditions & References With titanium tetrachloride in dichloromethane, Time= 0.5h, T= -78 Â°C Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7977 - 7980 View in Reaxys O

Zn(CN)2

Rx-ID: 18387354 View in Reaxys 420/824 Yield

Conditions & References Reaction Steps: 3 1: PCl5 2: 1.) Me3SnLi, 2.) MeLi 3: 84 percent / HCl / tetrahydrofuran / 15 h / Ambient temperature With (trimethylstannyl)lithium, hydrogenchloride, phosphorus pentachloride, methyllithium in tetrahydrofuran Jousseaume, Bernard; Vilcot, Nathalie; Ricci, Alfredo; Tiekink, Edward R. T.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 16; (1994); p. 2283 - 2288 View in Reaxys O

Zn(CN)2

Rx-ID: 18396262 View in Reaxys 421/824 Yield

Conditions & References Reaction Steps: 2 1: 1.) Me3SnLi, 2.) MeLi 2: 84 percent / HCl / tetrahydrofuran / 15 h / Ambient temperature With (trimethylstannyl)lithium, hydrogenchloride, methyllithium in tetrahydrofuran Jousseaume, Bernard; Vilcot, Nathalie; Ricci, Alfredo; Tiekink, Edward R. T.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 16; (1994); p. 2283 - 2288 View in Reaxys O

sulfur

Zn(CN)2

Rx-ID: 18727835 View in Reaxys 422/824

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Yield

Conditions & References Reaction Steps: 2 1: AlCl3 2: 25 percent / propylene oxide / H2O; acetone / Irradiation; pH neutral With aluminium trichloride, methyloxirane in water, acetone Sonawane, Harikisan; Bellur, Nanjundiah S.; Kulkarni, Dilip G.; Ayyangar, Nagaraj R.; Tetrahedron; vol. 50; nb. 4; (1994); p. 1243 - 1260 View in Reaxys Li

O B

Rx-ID: 1552042 View in Reaxys 423/824 Yield

Conditions & References With water, 1.) THF, hexane, Yield given. Multistep reaction Pelter; Warren; Wilson; Tetrahedron; vol. 49; nb. 14; (1993); p. 2988 - 3006 View in Reaxys

O O O

O HO O

Rx-ID: 1746476 View in Reaxys 424/824 Yield

Conditions & References Ambient temperature, Irradiation, without cyclohexane but in DMSO; after previous adsorption at room temp. for 2 h on different zeolites forms prepared from the commercial 13X and LZY-52, Product distribution, Mechanism Corma, Avelino; Garcia, Hermenegildo; Miranda, Miguel A.; Primo, Jaime; Sabater, Maria J.; Journal of Organic Chemistry; vol. 58; nb. 24; (1993); p. 6892 - 6894 View in Reaxys O

O O

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O O

O Pb

O O

Rx-ID: 1817058 View in Reaxys 425/824 Yield

Conditions & References With boron trifluoride diethyl etherate, 1) CHCl3, r.t., 2 h, 2) CDCl3, 60 deg C, 3 d, Yield given. Multistep reaction. Yields of byproduct given Morgan, Jacqueline; Buys, Irmi; Hambley, Trevor W.; Pinhey, John T.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 14; (1993); p. 1677 - 1682 View in Reaxys O

O O O O Si

O O

Rx-ID: 1817080 View in Reaxys 426/824 Yield

Conditions & References With boron trifluoride diethyl etherate, 1) CHCl3, r.t., 30 min, 2) CDCl3, 60 deg C, 28 h, Yield given. Multistep reaction. Yields of byproduct given Morgan, Jacqueline; Buys, Irmi; Hambley, Trevor W.; Pinhey, John T.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 14; (1993); p. 1677 - 1682 View in Reaxys Reaction Steps: 2 1: BF3-Et2O / chloroform 2: chloroform-d1 With BF3-Et2O in chloroform-d1, chloroform Morgan, Jacqueline; Buys, Irmi; Hambley, Trevor W.; Pinhey, John T.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 14; (1993); p. 1677 - 1682 View in Reaxys

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N O N

N N

Rx-ID: 2156570 View in Reaxys 427/824 Yield

Conditions & References With ethylmagnesium bromide, 1) THF, reflux, 2 h, 2) THF, reflux, 6 h, Yield given. Multistep reaction. Yields of byproduct given Black, David St. C.; Deacon, Glen B.; Edwards, Gavin L.; Gatehouse, Bryan M.; Australian Journal of Chemistry; vol. 46; nb. 9; (1993); p. 1323 - 1336 View in Reaxys

O O

I–

N+

Rx-ID: 2254087 View in Reaxys 428/824 Yield

Conditions & References

87 %

in tetrahydrofuran, -78 deg C to room temp. then room temp., 45 min Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

O Cl

(v5)

Rx-ID: 2333172 View in Reaxys 429/824 Yield

Conditions & References

62 % Chromat.

With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, Time= 20h, T= 25 °C Cho, Chan Sik; Itotani, Koichi; Uemura, Sakae; Journal of Organometallic Chemistry; vol. 443; nb. 2; (1993); p. 253 - 259 View in Reaxys

O O

Rx-ID: 2575335 View in Reaxys 430/824

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Yield

Conditions & References

68 %

in 1,3,5-trimethyl-benzene Birkhofer, Hermann; Beckhaus, Hans-Dieter; Ruechardt, Christoph; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 185 188 View in Reaxys

68 %

With 1,1-Diphenylethylene in 1,3,5-trimethyl-benzene, T= 170 - 220 °C , ΔG(excit), ΔH(excit), ΔS(excit), Kinetics, Thermodynamic data Birkhofer, Hermann; Beckhaus, Hans-Dieter; Peters, Karl; Schnering, Hans-Georg von; Ruechardt, Christoph; Chemische Berichte; vol. 126; nb. 7; (1993); p. 1693 - 1700 View in Reaxys Li

H B

O HO

Rx-ID: 2683996 View in Reaxys 431/824 Yield

Conditions & References 1.) THF, -78 deg C, 22 h, r.t., 16 h; 2.) CHCl3, reflux, 12 h, Yield given. Multistep reaction. Yields of byproduct given Pelter; Buss; Colclough; Singaram; Tetrahedron; vol. 49; nb. 32; (1993); p. 7077 - 7103 View in Reaxys Li

O B

Rx-ID: 2709029 View in Reaxys 432/824 Yield

Conditions & References With water, 1.) THF, hexane, Yield given. Multistep reaction Pelter; Warren; Wilson; Tetrahedron; vol. 49; nb. 14; (1993); p. 2988 - 3006 View in Reaxys

N O

Rx-ID: 2937306 View in Reaxys 433/824 Yield

Conditions & References With 1-phenylpyrazole, 1) THF, reflux, 2 h, 2) THF, reflux, 6 h, Yield given. Multistep reaction. Yields of byproduct given

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Black, David St. C.; Deacon, Glen B.; Edwards, Gavin L.; Gatehouse, Bryan M.; Australian Journal of Chemistry; vol. 46; nb. 9; (1993); p. 1323 - 1336 View in Reaxys O

O N HO

Rx-ID: 2965583 View in Reaxys 434/824 Yield

Conditions & References

78 %

With dinitrogen tetraoxide in tetrahydrofuran, Time= 0.166667h, T= -40 Â°C Kim, Yong Hae; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 74; nb. 1-4; (1993); p. 249 - 260 View in Reaxys OH

O OH

Rx-ID: 3382748 View in Reaxys 435/824 Yield

Conditions & References in benzene, Ambient temperature, Irradiation, varying alcohol concentration, Quantum yield Wagner, Peter J.; Zhang, Yuanda; Puchalski, Allen E.; Journal of Physical Chemistry; vol. 97; (1993); p. 13368 - 13374 View in Reaxys in benzene, Ambient temperature, Irradiation, varying acetophenone concentration, Quantum yield Wagner, Peter J.; Zhang, Yuanda; Puchalski, Allen E.; Journal of Physical Chemistry; vol. 97; (1993); p. 13368 - 13374 View in Reaxys O

(S)-2-chloro-butyric acid

Zn(CN)2

Rx-ID: 18572282 View in Reaxys 436/824 Yield

Conditions & References Reaction Steps: 2 1: NaOH 2: 86 percent / CH2Cl2 / added at -70 deg C, then 8 h at room temperature. AlCl3 can be added as well. With sodium hydroxide in dichloromethane Tolstikov, G. A.; Valitov, F. Kh.; Kuchin, A. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 6; (1982); p. 1328 1334,1170 - 1175 View in Reaxys Reaction Steps: 2 1: 57 percent / K2CO3 / CH2Cl2 / 1.) room temp., 15 min, 2.) reflux, 6 h 2: 87 percent / tetrahydrofuran / -78 deg C to room temp. then room temp., 45 min

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With potassium carbonate in tetrahydrofuran, dichloromethane Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys Reaction Steps: 3 1: 83 percent / K2CO3 / CH2Cl2 / 6 h / Heating 2: 95 percent / ethyl acetate / 24 h / Ambient temperature 3: 87 percent / tetrahydrofuran / -78 deg C to room temp. then room temp., 45 min With potassium carbonate in tetrahydrofuran, dichloromethane, ethyl acetate Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys O O

Zn(CN)2 O

Rx-ID: 18693315 View in Reaxys 437/824 Yield

Conditions & References Reaction Steps: 2 1: 50 percent / TiCl4, LiAlH4 / tetrahydrofuran / 20 h / Ambient temperature 2: 68 percent / 1,1-Diphenylethene / 1,3,5-trimethyl-benzene / 170 - 220 °C / ΔG(excit), ΔH(excit), ΔS(excit) With 1,1-Diphenylethylene, lithium aluminium tetrahydride, titanium tetrachloride in tetrahydrofuran, 1,3,5-trimethyl-benzene Birkhofer, Hermann; Beckhaus, Hans-Dieter; Peters, Karl; Schnering, Hans-Georg von; Ruechardt, Christoph; Chemische Berichte; vol. 126; nb. 7; (1993); p. 1693 - 1700 View in Reaxys

O –O

Zn(CN)2

N N+

Rx-ID: 18753682 View in Reaxys 438/824 Yield

Conditions & References Reaction Steps: 2 1: 95 percent / ethyl acetate / 24 h / Ambient temperature 2: 87 percent / tetrahydrofuran / -78 deg C to room temp. then room temp., 45 min in tetrahydrofuran, ethyl acetate Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys O

O O O O Si

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C H2

O O

H2 C

Rx-ID: 26941088 View in Reaxys 439/824 Yield

Conditions & References With BF3-Et2O in chloroform, the triacetate and the enol ether are dissolved in dry CHCl3, BF3-Et2O is added, the mixt. is stirred at room temp. for 30 min; the volatile components are evaporated at 25°C and 1 mmHg Morgan, Jacqueline; Buys, Irmi; Hambley, Trevor W.; Pinhey, John T.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 14; (1993); p. 1677 - 1682 ; (from Gmelin) View in Reaxys

O O Pb O O

H2 C

O O

Rx-ID: 26941601 View in Reaxys 440/824 Yield

Conditions & References

21 %, 21 %, in chloroform-d1, the Pb-compd. is stirred in dry CDCl3 at 60°C for 28 h; the reaction is monitored by 1H.-NMR, the solvent is 18 % evaporated off under reduced pressure, the residue is filtered in Et2O through silica gel, evapn. of solvent yielded a yellow oil, which is subjected to HPLC in AcOEt-light petroleum Morgan, Jacqueline; Buys, Irmi; Hambley, Trevor W.; Pinhey, John T.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 14; (1993); p. 1677 - 1682 ; (from Gmelin) View in Reaxys O O

O O

(v3) O O (v4)Pb O O Pb (v4) O (v7)O O (v7) O

(v3)

O O

O O O –O

O 2

O Pb

O Pb2+ (v0)

Rx-ID: 26941788 View in Reaxys 441/824

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Yield

Conditions & References

10 %, 37 %, in chloroform-d1, byproducts: anisol; the Pb-compd. is heated in dry CDCl3 at 60°C for 3 days; the ppt. is allowed to settle and 24 % analysis of the supernatant soln. by 1H.NMR, treatment of reaction mixt. with dry light petroleum, filtn. through silica gel, analysis of filtrate by GLC Morgan, Jacqueline; Buys, Irmi; Hambley, Trevor W.; Pinhey, John T.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 14; (1993); p. 1677 - 1682 ; (from Gmelin) View in Reaxys O

O O O

O O

Rx-ID: 2064379 View in Reaxys 442/824 Yield

Conditions & References With potassium perchlorate in N,N-dimethyl-formamide, Time= 30h, electrochemical reduction on a polycrystalline platinum electrode, Mechanism, Product distribution Garcia, V. G.; Montiel, V.; Aldaz, A.; Journal of Chemical Research, Miniprint; nb. 2; (1992); p. 540 - 553 View in Reaxys O

Rx-ID: 2141538 View in Reaxys 443/824 Yield 87 %

Conditions & References With potassium carbonate, palladium diacetate, tris-(o-tolyl)phosphine in benzene, Time= 5h, T= 80 °C Tsuji, Jiro; Nagashima, Hideo; Sato, Koji; Tetrahedron Letters; vol. 23; nb. 30; (1982); p. 3085 - 3088 View in Reaxys

87 %

With potassium carbonate, palladium diacetate, tris-(o-tolyl)phosphine in benzene, Heating nagashima, Hideo; Sato, Koji; Tsuii, Jiro; Tetrahedron; vol. 41; nb. 23; (1985); p. 5645 - 5651 View in Reaxys

75 %

With toluene-4-sulfonic acid in benzene, Ambient temperature, Irradiation Piva; Tetrahedron Letters; vol. 33; nb. 18; (1992); p. 2459 - 2460 View in Reaxys

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O O

Rx-ID: 2709981 View in Reaxys 444/824 Yield

Conditions & References

25 %, 62 %

in tetrahydrofuran, Ambient temperature Zhang, Li-Jun; Huang, Yao-Zeng; Jiang, Hong-Xia; Duan-Mu, Jun; Liao, Yi; Journal of Organic Chemistry; vol. 57; nb. 2; (1992); p. 774 - 777 View in Reaxys O

Rx-ID: 3840951 View in Reaxys 445/824 Yield 8 %, 78 %

Conditions & References With carbon monoxide, water, 1,8-diazabicyclo[5.4.0]undec-7-ene, selenium in tetrahydrofuran, Time= 24h, T= 120 °C , p= 22800Torr Nishiyama, Yutaka; Inoue, Jun; Teranishi, Kazuyo; Moriwaki, Masami; Hamanaka, Sawako; Tetrahedron Letters; vol. 33; nb. 42; (1992); p. 6347 - 6350 View in Reaxys

5 %, 73 %

With carbon monoxide, water, 1,8-diazabicyclo[5.4.0]undec-7-ene, selenium in tetrahydrofuran, Time= 24h, T= 120 °C , p= 22800Torr , other η-, η-diketone, other diketones, Product distribution Nishiyama, Yutaka; Inoue, Jun; Teranishi, Kazuyo; Moriwaki, Masami; Hamanaka, Sawako; Tetrahedron Letters; vol. 33; nb. 42; (1992); p. 6347 - 6350 View in Reaxys

O O

O OH

Rx-ID: 3867186 View in Reaxys 446/824 Yield

Conditions & References

64 %, 22 %, in dichloromethane, Time= 2h, T= -20 - 0 °C , var. enamines 11 % Adam, Waldemar; Andler, Simone; Heil, Markus; Voerckel, Volker; Journal of Organic Chemistry; vol. 57; nb. 9; (1992); p. 2680 - 2682

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View in Reaxys With hydrogenchloride, 1) CH2Cl2, -20 deg C -> 0 deg C, 2h, 2) 40-50 deg C, 30 min, Yield given. Multistep reaction. Yields of byproduct given Adam, Waldemar; Andler, Simone; Heil, Markus; Voerckel, Volker; Journal of Organic Chemistry; vol. 57; nb. 9; (1992); p. 2680 - 2682 View in Reaxys

H N

N N

O O O

Rx-ID: 1555907 View in Reaxys 447/824 Yield

Conditions & References

10.9 % Chromat., 5.4 % Chromat., 5.0 % Chromat., 15.6 % Chromat., 12.1 % Chromat.

With oxygen in ethyl acetate, T= 20 °C , further use of different solvents, Product distribution Blau, K.; Burgemeister, I.; Grasnick, J.; Voerckel, V.; Journal fuer Praktische Chemie (Leipzig); vol. 333; nb. 3; (1991); p. 455 - 466 View in Reaxys

O O

Rx-ID: 2032313 View in Reaxys 448/824 Yield

Conditions & References

50 %, 30 %

With tris(pyridine-2-carboxylato)manganese(III) Iwasawa, Nobuharu; Hayakawa, Satoshi; Isobe, Koichi; Narasaka, Koichi; Chemistry Letters; (1991); p. 1193 - 1196 View in Reaxys O

Rx-ID: 2035807 View in Reaxys 449/824 Yield 87 %

Conditions & References With triethyl borane, tri-n-butyl-tin hydride in hexane, toluene, Time= 10h, T= 25 °C

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Miura, Katsukiyo; Ichinose, Yoshifumi; Nozaki, Kyoko; Fugami, Keigo; Oshima, Koichiro; Utimoto, Kiitiro; Bulletin of the Chemical Society of Japan; vol. 62; nb. 1; (1989); p. 143 - 147 View in Reaxys in N,N,N,N,N,N-hexamethylphosphoric triamide, Ambient temperature, Irradiation, Rate constant, Mechanism Kimura, Norio; Takamuku, Setsuo; Bulletin of the Chemical Society of Japan; vol. 64; nb. 8; (1991); p. 2433 - 2437 View in Reaxys O O

H 2N

O N N H

H N

Rx-ID: 2180216 View in Reaxys 450/824 Yield 4 %, 14 %, 47 %, 2 %

Conditions & References in methanol, Time= 0.666667h, Irradiation, Further byproducts given Kim, Jong-Man; Bogdan, Michael A.; Mariano, Patrick S.; Journal of the American Chemical Society; vol. 113; nb. 24; (1991); p. 9251 - 9257 View in Reaxys

3 %, 5 %, 20 %, 8 %

in acetonitrile, Time= 0.5h, Irradiation, other cyclopropylamines, other solvents, Product distribution, Mechanism Kim, Jong-Man; Bogdan, Michael A.; Mariano, Patrick S.; Journal of the American Chemical Society; vol. 113; nb. 24; (1991); p. 9251 - 9257 View in Reaxys H

O N O

O O

O N O

Rx-ID: 2677944 View in Reaxys 451/824 Yield 76 %

Conditions & References With ammonium acetate in acetic acid, Time= 3h, T= 50 °C , p= 7500600Torr Agafonov, N. E.; Sedishev, I. P.; Dudin, A. V.; Kutin, A. A.; Stashina, G. A.; Zhulin, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 40; nb. 2.2; (1991); p. 366 - 372; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1991); p. 426 - 433 View in Reaxys With ammonium acetate in acetic acid, Time= 3h, T= 50 °C , p= 7500600Torr

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Agafonov, N. E.; Sedishev, I. P.; Dudin, A. V.; Kutin, A. A.; Stashina, G. A.; Zhulin, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 40; nb. 2.2; (1991); p. 366 - 372; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1991); p. 426 - 433 View in Reaxys O O– Na +

N O

Rx-ID: 3917912 View in Reaxys 452/824 Yield

Conditions & References

68 %, 4 %

With trifluorormethanesulfonic acid, trifluoroacetic acid, Time= 1.5h, T= 5 °C Ohwada, Tomohiko; Yamagata, Naoko; Shudo, Koichi; Journal of the American Chemical Society; vol. 113; nb. 4; (1991); p. 1364 - 1373 View in Reaxys O

4'-dimethylamino-biphenyl-4-yl magnesium iodide

Rx-ID: 11714388 View in Reaxys 453/824 Yield

Conditions & References Reaction Steps: 2 1: 93 percent / tetraisopropoxytitanium / diethyl ether / 0.5 h / -78 - 0 °C 2: 88 percent / acidic water / dioxane / 5 h / Heating With titanium(IV) isopropylate, water in 1,4-dioxane, diethyl ether Kulinkovich, O.G.; Sviridov, S.V.; Vasilevskii, D.A.; Savchenko, A.I.; Pritytskaya, T.S.; Journal of Organic Chemistry USSR (English Translation); vol. 27; nb. 2; (1991); p. 250 - 253; Zhurnal Organicheskoi Khimii; vol. 27; nb. 2; (1991); p. 294 298 View in Reaxys O (v5) (v5)

(v2)

(v5) (v5)

(v5)

Cl (v2)

(v2)

(v5)

(v5) Cl

(v5)

Cl (v2) (v5)

(v5)

Rx-ID: 26857903 View in Reaxys 454/824 Yield >99

Conditions & References With HCl Ikura, Kiyoshi; Ryu, Ilhyong; Ogawa, Akiya; Sonoda, Noboru; Harada, Shigeharu; Kasai, Nobutami; Organometallics; vol. 10; (1991); p. 528 - 529 ; (from Gmelin) View in Reaxys

O –O

Li+

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Rx-ID: 1673440 View in Reaxys 455/824 Yield

Conditions & References

57 %

in tetrahydrofuran, Time= 2h, T= -78 - 25 °C , Yield given Gong, Leyi; Leung-Toung, Regis; Tidwell, Thomas T.; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3634 - 3639 View in Reaxys

O –O

Li+

Rx-ID: 2033879 View in Reaxys 456/824 Yield

Conditions & References

57 %

in tetrahydrofuran, Time= 2h, T= -78 - 25 °C , Yields of byproduct given Gong, Leyi; Leung-Toung, Regis; Tidwell, Thomas T.; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3634 - 3639 View in Reaxys

Rx-ID: 2105740 View in Reaxys 457/824 Yield 22 % Spectr., 10 % Spectr., 68 % Spectr.

Conditions & References With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Time= 2.5h, T= 20 °C Christensen, Dorthe; Jorgensen, Karl Anker; Hazell, Rita G.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1990); p. 2391 - 2397 View in Reaxys

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O H+

N N

N –C

Rx-ID: 2226956 View in Reaxys 458/824 Yield

Conditions & References

52 %

With hydrogenchloride in chloroform, Heating Jones, Raymond C. F.; Nichols, John R.; Tetrahedron Letters; vol. 31; nb. 12; (1990); p. 1771 - 1774 View in Reaxys

O O

Rx-ID: 2295730 View in Reaxys 459/824 Yield

Conditions & References

42 % Spectr.

With trimethylsilyl iodide in chloroform-d1, Time= 4h, T= 22 °C Keinan, E.; Perez, D.; Sahai, M.; Shvily, R.; Journal of Organic Chemistry; vol. 55; nb. 9; (1990); p. 2927 - 2938 View in Reaxys O

Br O

Rx-ID: 2686115 View in Reaxys 460/824 Yield

Conditions & References With water, zinc, Time= 2h, Ambient temperature, Yield given. Yields of byproduct given Chan, T. H.; Li, C. J.; Wei, Z. Y.; Journal of the Chemical Society, Chemical Communications; nb. 6; (1990); p. 505 - 507 View in Reaxys With tin, water, Time= 4h, T= 80 °C , Yield given. Yields of byproduct given Chan, T. H.; Li, C. J.; Wei, Z. Y.; Journal of the Chemical Society, Chemical Communications; nb. 6; (1990); p. 505 - 507 View in Reaxys O O Tl Cl

Rx-ID: 2707592 View in Reaxys 461/824

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Yield

Conditions & References With methyllithium, 1) ether, 20 deg C; 2) ether, Yield given. Multistep reaction Marko, Istvan E.; Southern, J. Mike; Journal of Organic Chemistry; vol. 55; nb. 10; (1990); p. 3368 - 3370 View in Reaxys O

Rx-ID: 2896762 View in Reaxys 462/824 Yield

O O

Rx-ID: 2958672 View in Reaxys 463/824 Yield

O Br

Rx-ID: 2958749 View in Reaxys 464/824 Yield

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Br O

Rx-ID: 2958767 View in Reaxys 465/824 Yield

Conditions & References With tin, water, Time= 4h, T= 80 °C , Yield given. Yields of byproduct given Chan, T. H.; Li, C. J.; Wei, Z. Y.; Journal of the Chemical Society, Chemical Communications; nb. 6; (1990); p. 505 - 507 View in Reaxys With water, zinc, Time= 2h, Ambient temperature, Yield given. Yields of byproduct given Chan, T. H.; Li, C. J.; Wei, Z. Y.; Journal of the Chemical Society, Chemical Communications; nb. 6; (1990); p. 505 - 507 View in Reaxys

O O

Rx-ID: 2958780 View in Reaxys 466/824 Yield

Conditions & References With dibutylstannane, Time= 1h, T= 0 °C , p-dinitrobenzene as additive, Product distribution Shibata, Ikuya; Nakamura, Kenji; Baba, Akio; Matsuda, Haruo; Tetrahedron Letters; vol. 31; nb. 44; (1990); p. 6381 - 6384 View in Reaxys With para-dinitrobenzene, dibutylstannane, Time= 1h, T= 0 °C , Yield given. Yields of byproduct given Shibata, Ikuya; Nakamura, Kenji; Baba, Akio; Matsuda, Haruo; Tetrahedron Letters; vol. 31; nb. 44; (1990); p. 6381 - 6384 View in Reaxys O

Rx-ID: 3382345 View in Reaxys 467/824 Yield 22 % Chromat., 28 % Chromat.

Conditions & References With carbon monoxide, hydrogen, dodecacarbonyl-triangulo-triruthenium in N,N-dimethyl-formamide, Time= 16h, T= 150 °C , p= 76000.1Torr Abe, Fujio; Hayashi, Teruyuki; Tanaka, Masato; Chemistry Letters; nb. 5; (1990); p. 765 - 768 View in Reaxys

7 % Chromat., 51 % Chromat.

With carbon monoxide, hydrogen, dodecacarbonyl-triangulo-triruthenium in N,N-dimethyl-formamide, Time= 40h, T= 150 °C , p= 76000.1Torr Abe, Fujio; Hayashi, Teruyuki; Tanaka, Masato; Chemistry Letters; nb. 5; (1990); p. 765 - 768 View in Reaxys

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(v5)(v5)

(v5)

(v5)O

Ir P

(v8) (v4)

(v5)(v5) (v5)

Ir P (v8)

(v4)

O (v5)

Rx-ID: 26713679 View in Reaxys 468/824 Yield

Conditions & References

>99

in tetrahydrofuran, 70°C, 2d Tjaden, Erik B.; Stryker, Jeffrey M.; Journal of the American Chemical Society; vol. 112; nb. 17; (1990); p. 6420 - 6422 ; (from Gmelin) View in Reaxys

H N

Rx-ID: 1494572 View in Reaxys 469/824 Yield

Conditions & References With sulfur, T= 70 °C Carmack, Marvin; Behforouz, Mohammad; Berchtold, Glenn A.; Berkowitz, Samuel M.; Wiesler, Donald; Barone, Ralph; Journal of Heterocyclic Chemistry; vol. 26; (1989); p. 1305 - 1318 View in Reaxys

Rx-ID: 1763995 View in Reaxys 470/824 Yield

Conditions & References

3 %, 1 %, 1 %, 34 %

With 18-crown-6 ether, carbon dioxide in N,N-dimethyl-formamide, Time= 20h, T= 15 - 20 °C Yamamoto, Hiroshi; Mashino, Tadahiko; Nagano, Tetsuo; Hirobe, Masaaki; Tetrahedron Letters; vol. 30; nb. 31; (1989); p. 4133 - 4136 View in Reaxys O

O O N O

Rx-ID: 2042322 View in Reaxys 471/824 Yield 70 %

Conditions & References With triethylsilane, sodium dithionite in N,N,N,N,N,N-hexamethylphosphoric triamide, water, Time= 3h, T= 25 °C Kamimura, Akio; Kurata, Kiyoko; Ono, Noboru; Tetrahedron Letters; vol. 30; nb. 36; (1989); p. 4819 - 4820

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View in Reaxys 58 %

With 1-Benzyl-1,4-dihydronicotinamide in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 48h, Ambient temperature, Irradiation Ono; Tamura; Kaji; Journal of the American Chemical Society; vol. 105; nb. 12; (1983); p. 4017 - 4022 View in Reaxys O

O Si

Rx-ID: 2042725 View in Reaxys 472/824 Yield 51 %

Conditions & References With di(rhodium)tetracarbonyl dichloride in chloroform-d1, Time= 12h, T= 55 °C , Yield given Ikura, Kiyoshi; Ryu, Ilhyong; Ogawa, Akiya; Kambe, Nobuaki; Sonoda, Noboru; Tetrahedron Letters; vol. 30; nb. 49; (1989); p. 6887 - 6890 View in Reaxys O Cl

I O

Rx-ID: 2332311 View in Reaxys 473/824 Yield 90 %

Conditions & References With tetrabutylammonium tetrafluoroborate, (2,2'-bipyridine)nickel(II) dibromide in acetonitrile, Ambient temperature, zinc rod as the anode, vitreous carbon gauze as the cathode, 0.1 A Marzouk, H.; Rollin, Y.; Folest, J. C.; Nedelec, J. Y.; Perichon, J.; Journal of Organometallic Chemistry; vol. 369; (1989); p. C47 - C50 View in Reaxys

Rx-ID: 2690857 View in Reaxys 474/824 Yield

Conditions & References With hydrogenchloride, (-)-DAIB in toluene, T= 0 °C , various molar ratio of reagents, other dialkylzincs; alkylscrambling experiments, Rate constant, Mechanism, Product distribution Kitamura, M.; Okada, S.; Suga, S.; Noyori, R.; Journal of the American Chemical Society; vol. 111; nb. 11; (1989); p. 4028 4036 View in Reaxys

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Rx-ID: 2710762 View in Reaxys 475/824 Yield 75 %, 15 %

Conditions & References in toluene, Time= 5h, T= 20 °C Boudin, Alain; Cerveau, Genevieve; Chuit, Claude; Corriu, Robert J.P.; Reye, Catherine; Tetrahedron; vol. 45; nb. 1; (1989); p. 171 - 180 View in Reaxys

75 %, 15 %

in toluene, Time= 5h, T= 20 °C , further carbonyl compounds, further Grignard/TDA-1 complexes Boudin, Alain; Cerveau, Genevieve; Chuit, Claude; Corriu, Robert J.P.; Reye, Catherine; Tetrahedron; vol. 45; nb. 1; (1989); p. 171 - 180 View in Reaxys O

O O

–O

S Cl

S O

Rx-ID: 3021222 View in Reaxys 476/824 Yield 98 % Chromat.

Conditions & References With potassium superoxide in acetonitrile, Time= 6h, T= -35 °C Kim, Yong Hae; Kim, Kyoung Soo; Lee, Hyeon Kyu; Tetrahedron Letters; vol. 30; nb. 46; (1989); p. 6357 - 6360 View in Reaxys

O O

Rx-ID: 3756881 View in Reaxys 477/824 Yield 3.3 %

Conditions & References With morpholine, sulfur, T= 70 °C Carmack, Marvin; Behforouz, Mohammad; Berchtold, Glenn A.; Berkowitz, Samuel M.; Wiesler, Donald; Barone, Ralph; Journal of Heterocyclic Chemistry; vol. 26; (1989); p. 1305 - 1318 View in Reaxys

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NH 2 S S NH 2

H N

Rx-ID: 3868195 View in Reaxys 478/824 Yield

Conditions & References

66 %, 42 %, With toluene-4-sulfonic acid in toluene, Time= 5h, Heating 65 % Trapani, Giuseppe; Latrofa, Andrea; Reho, Antonia; Liso, Gaetano; Journal of Heterocyclic Chemistry; vol. 26; (1989); p. 721 - 724 View in Reaxys

Br 2

Rx-ID: 3922163 View in Reaxys 479/824 Yield 75 %, 15 %

Conditions & References With carbon disulfide in tetrahydrofuran, Time= 5h, T= 20 °C , further carbonyl compounds, further Grignard/TDA-1 complexes Boudin, Alain; Cerveau, Genevieve; Chuit, Claude; Corriu, Robert J.P.; Reye, Catherine; Tetrahedron; vol. 45; nb. 1; (1989); p. 171 - 180 View in Reaxys O

(HBPz3 *)Rh(CO)(Ph)-C(O)C2H5

Rx-ID: 5931103 View in Reaxys 480/824 Yield 82 %

Conditions & References With zinc dibromide in dichloromethane, Time= 4h, T= 25 °C Ghosh, Chanchal K.; Graham, William A. G.; Journal of the American Chemical Society; vol. 111; nb. 1; (1989); p. 375 376 View in Reaxys

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H B

t-BuLi O

Rx-ID: 5931109 View in Reaxys 481/824 Yield

Conditions & References With N-chloro-succinimide, 2,4,6-trimethylphenyl bromide, 1.) THF-hexane, -78 deg C to 25 deg C, 1.5 h; 2.) THF, -127 deg C to 25 deg C, 20 h, Yield given. Multistep reaction Pelter, Andrew; Smith, Keith; Elgendy, Said; Rowlands, Martin; Tetrahedron Letters; vol. 30; nb. 41; (1989); p. 5643 - 5646 View in Reaxys O

Rx-ID: 819435 View in Reaxys 482/824 Yield

Conditions & References

67 %

With tri-n-butyl-tin hydride, Time= 0.5h, T= 200 °C Chao, Herbert S.-I.; Synthetic Communications; vol. 18; nb. 11; (1988); p. 1207 - 1212 View in Reaxys With barium sulfate-supported palladium, T= 120 °C , Hydrogenation Reichert; Posemann; Archiv der Pharmazie (Weinheim, Germany); vol. 281; (1943); p. 189 View in Reaxys

N N O

Rx-ID: 2154662 View in Reaxys 483/824 Yield 0.5 % Chromat., 6.9 % Chromat., 90 % Chromat., 1 % Chromat.

Conditions & References With η,η,η,η-Tetraphenylporphin-Zink, oxygen in benzene, Time= 0.5h, T= 20 °C , Irradiation, other substituted diazomethanes; other (or none) sensitizer; var. reaction conditions, Product distribution, Quantum yield, Mechanism Ishiguro, Katsuya; Hirano, Yukimichi; Sawaki, Yasuhiko; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5397 5405 View in Reaxys

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(v4)

P (v4)

(v2)

Pd (v4)

Rx-ID: 2254764 View in Reaxys 484/824 Yield

Conditions & References in tetrahydrofuran, hexane, Time= 2h, p= 22800Torr , Ambient temperature, Yield given. Yields of byproduct given Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 View in Reaxys

(v2)

(v4)

Rx-ID: 2254765 View in Reaxys 485/824 Yield

Conditions & References With BrClMg, Time= 2h, p= 22800Torr , Ambient temperature, Yield given. Yields of byproduct given Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 View in Reaxys

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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(v4)

P (v4)

H (v2)

Pd (v4)

Rx-ID: 2254800 View in Reaxys 486/824 Yield

Conditions & References With carbon monoxide, BrClMg, Time= 2h, p= 22800Torr , Ambient temperature, Yield given Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 View in Reaxys

(v4)

P (v4)

(v2)

Pd (v4)

Rx-ID: 2254931 View in Reaxys 487/824 Yield

(v4)

P (v4)

(v2)

Pd (v4)

Rx-ID: 2425657 View in Reaxys 488/824 Yield

Conditions & References With carbon monoxide, BrClMg, Time= 2h, p= 22800Torr , Ambient temperature, Yield given

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 View in Reaxys O (v2)

O HO

Rx-ID: 2707474 View in Reaxys 489/824 Yield

Conditions & References With BrClMg, Pd Complex, palladium in tetrahydrofuran, Time= 16h, p= 22800Torr , Ambient temperature, Yield given. Yields of byproduct given Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 View in Reaxys O (v2)

O HO

Rx-ID: 2707475 View in Reaxys 490/824 Yield

Conditions & References With BrClMg, Pd Complex, palladium in tetrahydrofuran, Time= 16h, p= 22800Torr , Ambient temperature, Yield given Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 View in Reaxys O O

O H

(v2)

Rx-ID: 2707476 View in Reaxys 491/824 Yield

Conditions & References With carbon monoxide, BrClMg, Pd Complex, palladium in tetrahydrofuran, Time= 16h, p= 22800Torr , Ambient temperature, Yield given Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 View in Reaxys

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Rx-ID: 2714881 View in Reaxys 492/824 Yield

Conditions & References With carbon monoxide, diethylzinc, BrClMg, Pd Complex, palladium in tetrahydrofuran, Time= 16h, p= 22800Torr , Ambient temperature, var. Pd complexes, ethylmetals, Product distribution Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 View in Reaxys O

N Li

Rx-ID: 2926344 View in Reaxys 493/824 Yield

Conditions & References With n-butyllithium, acetic acid, 1.) hexane, THF, 2 h, -40 deg C -> -5 deg C; 2.) cyclohexane-ether, 3 h, -5 deg C -> 10 deg C; 3.) 16 h, ether, Yield given. Multistep reaction El-Jazouli, Mustapha; Lage, Nadia; Masson, Serge; Thuillier, Andre; Bulletin de la Societe Chimique de France; nb. 5; (1988); p. 883 - 888 View in Reaxys

(v4)

P (v4)

(v2)

Pd (v4)

O O

Rx-ID: 26144168 View in Reaxys 494/824 Yield <1, 7 %, 4 %

Conditions & References With carbon monoxide in tetrahydrofuran, High Pressure; 0.05 mmol Pd compound, 0.1 mmol Et2Zn, 2.5 ml THF, CO 30 atm (at -50°), stirred at 25°C for 2 h in presence of 0.2 mmol MgClBr, (yield of PhCEt(OH)COEt/PhCOCEt2(OH): 68percent), previous product ratio for previous conditions; GC-MS, GC

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Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

(v4)

P (v4)

Pd (v4)

Rx-ID: 26144169 View in Reaxys 495/824 Yield

Conditions & References

0 %, 0 %, 0 %, 0 %

With carbon monoxide in tetrahydrofuran, hexane, High Pressure; 0.05 mmol Pd compound, 0.1 mmol Et3B, 2,5 ml THF/ hexane (24/1), CO 30 atm (at -50°C), stirred for 2 h at 25°C; GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

(v4)

P (v4)

Pd (v4)

Rx-ID: 26144170 View in Reaxys 496/824 Yield 0 %, 0 %, 0 %, 15 %

Conditions & References With carbon monoxide in tetrahydrofuran, hexane, High Pressure; 0.05 mmol Pd compound, 0.1 mmol Et3Al, 2,5 ml THF/ hexane (24/1), CO 30 atm (at -50°C), stirred for 2 h at 25°C; GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

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O (v2)

Rx-ID: 26159266 View in Reaxys 497/824 Yield 0 %, 0 %, 0 %, 0 %, 99 %

Conditions & References With carbon monoxide, dichlorobis(trimethylphosphine)palladium in tetrahydrofuran, High Pressure; 0.5 mmol PhCOCl, 1 mmol Et2Zn, 2 mmol MgClBr, 0.05 mmol Pd complex, 20 ml THF, CO 30 atm, stirred at 25°C for 16 h; GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

3 %, <0.5, 75 %

With carbon monoxide, (bis(tricyclohexyl)phosphine)palladium(II) dichloride in tetrahydrofuran, High Pressure; 0.5 mmol PhCOCl, 1 mmol Et2Zn, 2 mmol MgClBr, 0.05 mmol Pd complex, 20 ml THF, CO 30 atm, stirred at 25°C for 16 h, (yield of PhCEt(OH)COCEt/PhCOCEt2(OH): 1percent); GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

2 %, 1 %, 51 %

With carbon monoxide, [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride in tetrahydrofuran, High Pressure; 0.5 mmol PhCOCl, 1 mmol Et2Zn, 2 mmol MgClBr, 0.05 mmol Pd complex, 20 ml THF, CO 30 atm, stirred at 25°C for 16 h, (yield of PhCEt(OH)COEt/PhCOCEt2(OH): 7percent); GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

7 %, 2 %, 23 %

With carbon monoxide, bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran, High Pressure; 0.5 mmol PhCOCl, 1 mmol Et2Zn, 2 mmol MgClBr, 0.05 mmol Pd complex, 20 ml THF, CO 30 atm, stirred at 25°C for 16 h, (yield of PhCEt(OH)COEt/PhCOCEt2(OH): 17percent); GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

8 %, 1 %, 15 %

With carbon monoxide, bis(tris(4-fluoro)phenylphosphine)palladium dichloride in tetrahydrofuran, High Pressure; 0.5 mmol PhCOCl, 1 mmol Et2Zn, 2 mmol MgClBr, 0.05 mmol Pd complex, 20 ml THF, CO 30 atm, stirred at 25°C for 16 h, (yield of PhCEt(OH)COEt/PhCOCEt2(OH): 20percent); GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

0 %, 0 %, 0 With carbon monoxide, bis(benzonitrile)palladium(II) dichloride in tetrahydrofuran, byproducts: PhCO2(CH2)4Cl; High Pres%, 0 %, 3 % sure; 0.5 mmol PhCOCl, 1 mmol Et2Zn, 2 mmol MgClBr, 0.05 mmol Pd complex, 20 ml THF, CO 30 atm, stirred at 25°C for 16 h, (yield of PhCO2(CH2)4Cl: 22percent); GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

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(v2)

(v4)

Rx-ID: 26159278 View in Reaxys 498/824 Yield

Conditions & References

3 %, 8 %, 9 %

With carbon monoxide in tetrahydrofuran, High Pressure; 0.05 mmol Pd compound, 0.1 mmol Et2Zn, 2.5 ml THF, CO 30 atm (at -50°), stirred at 25°C for 2 h in presence of 0.2 mmol MgClBr, (yield of PhCEt(OH)COEt/PhCOCEt2(OH): 61percent); GCMS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

(v4)

P (v4)

Pd (v4)

Rx-ID: 26441379 View in Reaxys 499/824 Yield

Conditions & References

<1, <1, 5 %, With carbon monoxide, ethylmagnesium bromide in tetrahydrofuran, High Pressure; 0.05 mmol Pd compound, 0.1 mmol 8% EtMgBr, 2,5 ml THF, CO 30 atm (at -50°C), stirred for 2 h at 25°C; GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

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(v4)

P (v4)

Pd (v4)

Rx-ID: 26441380 View in Reaxys 500/824 Yield

Conditions & References

0 %, 0 %, 0 %, 1 %

With carbon monoxide in tetrahydrofuran, hexane, High Pressure; 0.05 mmol Pd compound, 0.1 mmol Et2AlCl, 2,5 ml THF/ hexane (24/1), CO 30 atm (at -50°C), stirred for 2 h at 25°C; GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

(v4)

P (v4)

(v2)

Pd (v4)

Rx-ID: 26441381 View in Reaxys 501/824 Yield 8 %, 2 %

Conditions & References With carbon monoxide in tetrahydrofuran, High Pressure; 0.05 mmol Pd compound, 0.1 mmol Et2Cd, 2,5 ml THF, CO 30 atm (at -50°C), stirred for 2 h at 25°C in presence of 0.2 mmol MgClBr (yield of PhCEt(OH)COEt/PhCOCEt2(OH): 71percent); GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

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(v4)

P (v4)

(v1)

Pd (v4)

Rx-ID: 26441383 View in Reaxys 502/824 Yield

Conditions & References

12 %, 21 %

With carbon monoxide in tetrahydrofuran, High Pressure; 0.05 mmol Pd compound, 0.1 mmol EtCu, 2,5 ml THF, CO 30 atm (at -50°C), stirred for 2 h at 25°C in presence of 0.1 mmol MgBrI (yield of PhCEt(OH)COEt/PhCOCEt2(OH): 17percent); GCMS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

(v4)

P (v4)

(v2)

(v4)

Rx-ID: 26441384 View in Reaxys 503/824 Yield 0 %, 56 %

Conditions & References With carbon monoxide in tetrahydrofuran, High Pressure; 0.05 mmol Pd compound, 0.1 mmol EtZnCl, 2,5 ml THF, CO 30 atm (at -50°C), stirred for 2 h at 25°C in presence of 0.1 mmol MgClBr (yield of PhCEt(OH)COEt/PhCOCEt2(OH): 21percent); GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

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(v4)

P (v4)

(v2)

(v4)

Rx-ID: 26441385 View in Reaxys 504/824 Yield

Conditions & References

<1, <1, 3 %, With carbon monoxide in diethyl ether, High Pressure; 0.05 mmol Pd compound, 0.1 mmol EtMnI, 2,5 ml Et2O, CO 30 atm (at <1 -50°C), stirred for 2 h at 25°C in presence of 0.1 mmol MgBrI; GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

(v4)

P (v4)

(v2)

Pd (v4)

O OH

Rx-ID: 26441386 View in Reaxys 505/824 Yield 0 %, 0 %, 0 %, 91 %

Conditions & References With carbon monoxide in tetrahydrofuran, High Pressure; 0.05 mmol Pd compound, 0.1 mmol Et2Hg, 2,5 ml THF, CO 30 atm (at -50°C), stirred for 2 h at 25°C in presence of 0.2 mmol MgClBr; GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

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(v4)

P (v4)

(v4)

Rx-ID: 26441387 View in Reaxys 506/824 Yield

Conditions & References

0 %, 0 %, 0 %, 0 %

With carbon monoxide in tetrahydrofuran, High Pressure; 0.05 mmol Pd compound, 0.1 mmol Et4Sn, 2,5 ml THF, CO 30 atm (at -50°C), stirred for 2 h at 25°C; GC-MS, GC Yamashita, Hiroshi; Kobayashi, Toshi-aki; Sakakura, Toshiyasu; Tanaka, Masato; Journal of Organometallic Chemistry; vol. 356; (1988); p. 125 - 132 ; (from Gmelin) View in Reaxys

Rx-ID: 1710807 View in Reaxys 507/824 Yield

Conditions & References

15 % Chromat., 19 % Chromat.

With tetrakis(triphenylphosphine) palladium(0), Time= 20h, T= 100 °C

15 % Chromat., 19 % Chromat.

With tetrakis(triphenylphosphine) palladium(0), Time= 20h, T= 100 °C , reaction var. organic halides with propanoyltributyltin, var. catalysts, Product distribution

Kosugi, Masanori; Naka, Hiroyuki; Harada, Saburo; Sano, Hiroshi; Migita, Toshihiko; Chemistry Letters; (1987); p. 1371 - 1372 View in Reaxys

Kosugi, Masanori; Naka, Hiroyuki; Harada, Saburo; Sano, Hiroshi; Migita, Toshihiko; Chemistry Letters; (1987); p. 1371 - 1372 View in Reaxys O

HO O

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O O O

Rx-ID: 1970427 View in Reaxys 508/824 Yield

Conditions & References With oxygen in benzene, Time= 10h, T= 40 °C , Irradiation, other solvent cyclohexane, other time, temp., without O2, Product distribution Rao, T. S. S.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 329; nb. 4; (1987); p. 617 - 625 View in Reaxys O O

Rx-ID: 2038127 View in Reaxys 509/824 Yield

Conditions & References

63 %, 18 %

With lead(IV) acetate, perchloric acid in various solvent(s), Time= 30h, T= 25 °C Yamauchi, Takayoshi; Nakao, Kenji; Fujii, Kyoichi; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 1433 - 1436 View in Reaxys O

H 2N

Rx-ID: 2141260 View in Reaxys 510/824 Yield

Conditions & References

92 %

With dinitrogen tetraoxide in acetonitrile, Time= 0.166667h, T= -35 °C Shim, Sung Bo; Kim, Kweon; Kim, Yong Hae; Tetrahedron Letters; vol. 28; nb. 6; (1987); p. 645 - 648 View in Reaxys O

O N N

O O

HO O

Rx-ID: 2203536 View in Reaxys 511/824 Yield

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-1 F (v4)

B FF

Sn N+ N

Rx-ID: 2254885 View in Reaxys 512/824 Yield

Conditions & References

48 %

With palladium diacetate in acetonitrile, Time= 5h, Ambient temperature Kikukawa, Kiyoshi; Idemoto, Tohru; Katayama, Atsuhiko; Kono, Kiyoshi; Wada, Fumio; Matsuda, Tsutomu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 1511 - 1514 View in Reaxys

40 %

With palladium diacetate in acetonitrile, Time= 6h, p= 6619.6Torr , Heating Kikukawa,Kiyoshi; Kono, Kiyoshi; Wada, Fumio; Matsuda, Tsutomu; Chemistry Letters; (1982); p. 35 - 36 View in Reaxys O

Br O

Rx-ID: 2686114 View in Reaxys 513/824 Yield

Conditions & References

80 % Chromat., 0.5 % Chromat., 18 % Chromat.

With lanthanum bromide, lithium perchlorate in tetrahydrofuran, electrolysis Fry, Albert J.; Susla, Marko; Weltz, Michael; Journal of Organic Chemistry; vol. 52; nb. 12; (1987); p. 2496 - 2498 View in Reaxys

O O

Rx-ID: 2707887 View in Reaxys 514/824 Yield 84 %

Conditions & References With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, Time= 3h, T= 65 Â°C Yamada, Jun-ichi; Yamamoto, Yoshinori; Journal of the Chemical Society, Chemical Communications; nb. 17; (1987); p. 1302 - 1303 View in Reaxys

S O S

Rx-ID: 2853126 View in Reaxys 515/824

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Yield

Conditions & References Yield given. Multistep reaction Wladislaw, B.; Marzorati, L.; Uchoa, R. B.; Phosphorus and Sulfur and the Related Elements; vol. 32; (1987); p. 87 - 90 View in Reaxys

O O

Rx-ID: 2895391 View in Reaxys 516/824 Yield

Conditions & References

41 % Chromat., 43 % Chromat.

Rx-ID: 2950166 View in Reaxys 517/824 Yield

Conditions & References

50 % Chromat., 50 % Chromat.

O O

Br O O

Rx-ID: 2958692 View in Reaxys 518/824 Yield

Conditions & References

66 % Chromat., 30 % Chromat.

O Br

Rx-ID: 2958748 View in Reaxys 519/824 Yield 84 %, 3 %

Conditions & References With lanthanum bromide, lithium perchlorate in tetrahydrofuran, electrolysis

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Fry, Albert J.; Susla, Marko; Weltz, Michael; Journal of Organic Chemistry; vol. 52; nb. 12; (1987); p. 2496 - 2498 View in Reaxys

O O N O

Rx-ID: 2977637 View in Reaxys 520/824 Yield

Conditions & References

68 %

With 2-methylpropan-2-thiol in isopropyl alcohol, Ambient temperature, Irradiation Hasebe, Masato; Tsuchiya, Takashi; Tetrahedron Letters; vol. 28; nb. 49; (1987); p. 6207 - 6210 View in Reaxys O O

O S

Rx-ID: 3383921 View in Reaxys 521/824 Yield

Conditions & References With sodium hydride in N,N,N,N,N,N-hexamethylphosphoric triamide, T= 20 Â°C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Gompper, Rudolf; Vogt, Hans-Hubert; Chemische Berichte; vol. 114; nb. 8; (1981); p. 2866 - 2883 View in Reaxys With lithium hydride in tetrachloromethane, Yield given. Yields of byproduct given. Title compound not separated from byproducts Lazana, M. Celina R. L. R.; Franco, M. Luisa T. M. B.; Herold, Bernardo J.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 1399 - 1406 View in Reaxys

O S

Rx-ID: 3383922 View in Reaxys 522/824 Yield

Conditions & References With lithium hydride in N,N,N,N,N,N-hexamethylphosphoric triamide, Yield given. Yields of byproduct given. Title compound not separated from byproducts Lazana, M. Celina R. L. R.; Franco, M. Luisa T. M. B.; Herold, Bernardo J.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 1399 - 1406 View in Reaxys

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O S

Rx-ID: 3383923 View in Reaxys 523/824 Yield

Conditions & References With lithium hydride in 1,4-dioxane, also other solvents, other alkali hydrides, Product distribution Lazana, M. Celina R. L. R.; Franco, M. Luisa T. M. B.; Herold, Bernardo J.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 1399 - 1406 View in Reaxys With lithium hydride in 1,4-dioxane, Yield given. Yields of byproduct given. Title compound not separated from byproducts Lazana, M. Celina R. L. R.; Franco, M. Luisa T. M. B.; Herold, Bernardo J.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 1399 - 1406 View in Reaxys With lithium hydride in tetrahydrofuran, Yield given. Yields of byproduct given. Title compound not separated from byproducts Lazana, M. Celina R. L. R.; Franco, M. Luisa T. M. B.; Herold, Bernardo J.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 1399 - 1406 View in Reaxys

Rx-ID: 3696373 View in Reaxys 524/824 Yield

Conditions & References With potassium hydroxide, dihydrogen peroxide, 1) CHCl3, acetic acid, 55 deg C - 60 deg C, 2.5 h, 2) dioxane, reflux, 0.5 h, Yield given. Multistep reaction Barbero, Margherita; Cadamuro, Silvano; Ceruti, Maurizio; Degani, Iacapo; Fochi, Rita; Regondi, Valeria; Gazzetta Chimica Italiana; vol. 117; nb. 4; (1987); p. 227 - 236 View in Reaxys

O N O

Rx-ID: 3917563 View in Reaxys 525/824

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Yield

Conditions & References

73 %, 50 %, With trifluorormethanesulfonic acid, Time= 6.5h, T= 0 - 5 °C 22 % Ohwada, Tomohiko; Ohta, Toshiharu; Shudo, Koichi; Tetrahedron; vol. 43; nb. 2; (1987); p. 297 - 305 View in Reaxys O

Zn(CN)2

Cl O

Rx-ID: 18516641 View in Reaxys 526/824 Yield

Conditions & References Reaction Steps: 2 1: 95 percent / HBF4 / diethyl ether / 0.17 h / 105 - 110 °C 2: 1) 36percent H2O2, 2) 20percent KOH / 1) CHCl3, acetic acid, 55 deg C - 60 deg C, 2.5 h, 2) dioxane, reflux, 0.5 h With potassium hydroxide, tetrafluoroboric acid, dihydrogen peroxide in diethyl ether Barbero, Margherita; Cadamuro, Silvano; Ceruti, Maurizio; Degani, Iacapo; Fochi, Rita; Regondi, Valeria; Gazzetta Chimica Italiana; vol. 117; nb. 4; (1987); p. 227 - 236 View in Reaxys O

Zn(CN)2

HO O

Rx-ID: 18527630 View in Reaxys 527/824 Yield

Conditions & References Reaction Steps: 2 1: 90 percent / HBF4 / diethyl ether / 0.17 h / 105 - 110 °C 2: 1) 36percent H2O2, 2) 20percent KOH / 1) CHCl3, acetic acid, 55 deg C - 60 deg C, 2.5 h, 2) dioxane, reflux, 0.5 h With potassium hydroxide, tetrafluoroboric acid, dihydrogen peroxide in diethyl ether Barbero, Margherita; Cadamuro, Silvano; Ceruti, Maurizio; Degani, Iacapo; Fochi, Rita; Regondi, Valeria; Gazzetta Chimica Italiana; vol. 117; nb. 4; (1987); p. 227 - 236 View in Reaxys

Sn Br

Rx-ID: 26813484 View in Reaxys 528/824 Yield 15 %, 19 %

Conditions & References With tetrakis(triphenylphosphine) palladium(0), 100°C, 20 h; GLC Kosugi, Masanori; Naka, Hiroyuki; Harada, Saburo; Sano, Hiroshi; Migita, Toshihiko; Chemistry Letters; (1987); p. 1371 - 1372 ; (from Gmelin) View in Reaxys

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O O

HO H 2N

Rx-ID: 1587210 View in Reaxys 529/824 Yield

Conditions & References

55 %, 33 %

With N,N'-bis(salicylidene)ethylenediaminatocobalt(III) hydroxide, oxygen, Time= 1h, Ambient temperature Nishinaga, Akira; Yamazaki, Shigekazu; Matsuura, Teruo; Tetrahedron Letters; vol. 27; nb. 23; (1986); p. 2649 - 2652 View in Reaxys

Te Te

O O

Rx-ID: 1746475 View in Reaxys 530/824 Yield

Conditions & References With sodium, 1.) THF, reflux, 7 h; 2.) THF-DMF, reflux, 20 h, Yield given. Multistep reaction Uemura, Sakae; Fukuzawa, Shin-ichi; Yamauchi, Takayoshi; Hattori, Kaneaki; Mizutaki, Shoichi; Tamaki, Kentaro; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 1983 1987 View in Reaxys

O O

Rx-ID: 1818929 View in Reaxys 531/824 Yield

Conditions & References

73 %

With boron tribromide in dichloromethane, Time= 1h, T= 0 Â°C Napolitano, Elio; Fiaschi, Rita; Mastrorilli, Ettore; Synthesis; nb. 1; (1986); p. 122 - 125 View in Reaxys O O

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O O

Rx-ID: 2036501 View in Reaxys 532/824 Yield

Conditions & References

53 % Turn- in methanol, T= 25 °C , Irradiation, starting material adsorbed on silica gel, Product distribution, Mechanism ov., 3 % Turnov., 16 Mayo, Paul de; Ramnath, N.; Canadian Journal of Chemistry; vol. 64; (1986); p. 1293 - 1296 % Turnov., View in Reaxys 2 % Turnov. O

Rx-ID: 2060897 View in Reaxys 533/824 Yield

Conditions & References

80 %

Feringa, Ben L.; Jansen, F. G. A.; Tetrahedron Letters; vol. 27; nb. 4; (1986); p. 507 - 508 View in Reaxys O

O N

Rx-ID: 2100764 View in Reaxys 534/824 Yield

Conditions & References

84 %

in tetrahydrofuran, diethyl ether, Time= 1h, T= 0 °C Itsuno, Shinichi; Miyazaki, Koji; Ito, Koichi; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 3033 - 3036 View in Reaxys

84 %

in tetrahydrofuran, diethyl ether, Time= 1h, T= 0 °C , further organometallic compounds and temperatures, Mechanism Itsuno, Shinichi; Miyazaki, Koji; Ito, Koichi; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 3033 - 3036 View in Reaxys O

O N Mg Br

Rx-ID: 2100765 View in Reaxys 535/824 Yield 57 %

Conditions & References in tetrahydrofuran, diethyl ether, Time= 1h, T= 65 °C Itsuno, Shinichi; Miyazaki, Koji; Ito, Koichi; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 3033 - 3036 View in Reaxys

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O O

H 2N

Rx-ID: 2532824 View in Reaxys 536/824 Yield 55 %, 33 %

Conditions & References With N,N'-bis(salicylidene)ethylenediaminatocobalt(III) hydroxide, oxygen in methanol, Time= 1h, Ambient temperature Nishinaga, Akira; Yamazaki, Shigekazu; Matsuura, Teruo; Tetrahedron Letters; vol. 27; nb. 23; (1986); p. 2649 - 2652 View in Reaxys O

Rx-ID: 3952111 View in Reaxys 537/824 Yield 82 %

Conditions & References With N,N,N,N,N,N-hexamethylphosphoric triamide, zinc(II) acetylacetonate, triphenylphosphine, bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran, Time= 10.5h, T= 50 - 55 °C , p= 760Torr , var.: reagent, time, solvent Wakita, Yoshiaki; Yasunaga, Tomoyuki; Akita, Masahiro; Kojima, Masaharu; Journal of Organometallic Chemistry; vol. 301; (1986); p. C17 - C20 View in Reaxys O

Rx-ID: 21549565 View in Reaxys 538/824 Yield

Conditions & References Reaction Steps: 2 1: 73 percent / tetrahydrofuran / -78 deg C then warming to room temp. 2: 80 percent in tetrahydrofuran Feringa, Ben L.; Jansen, F. G. A.; Tetrahedron Letters; vol. 27; nb. 4; (1986); p. 507 - 508 View in Reaxys O

Rx-ID: 2105739 View in Reaxys 539/824 Yield

Conditions & References With acetic acid, Time= 24h, T= 20 °C , Yield given Jazouli, Mustapha El; Masson, Serge; Thuillier, Andre; Journal of the Chemical Society, Chemical Communications; nb. 22; (1985); p. 1598 - 1599 View in Reaxys

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N N

Rx-ID: 2154661 View in Reaxys 540/824 Yield

Conditions & References With methylphenylsulfonate, oxygen, η,η,η,η-Tetraphenylporphin-Zink in acetonitrile, benzene, Irradiation, building of (18)O2 is investigated, Yield given. Yields of byproduct given Ishiguro, Katsuya; Tomizawa, Kohtaro; Sawaki, Yasuhiko; Iwamura, Hiizu; Tetrahedron Letters; vol. 26; nb. 31; (1985); p. 3723 - 3726 View in Reaxys With methylphenylsulfonate, oxygen, η,η,η,η-Tetraphenylporphin-Zink in acetonitrile, benzene, Irradiation, building in of (18)O2 is investigated, Yield given. Yields of byproduct given Ishiguro, Katsuya; Tomizawa, Kohtaro; Sawaki, Yasuhiko; Iwamura, Hiizu; Tetrahedron Letters; vol. 26; nb. 31; (1985); p. 3723 - 3726 View in Reaxys With methylphenylsulfonate, oxygen, η,η,η,η-Tetraphenylporphin-Zink in acetonitrile, benzene, Irradiation, building in of (18)O2 is investigated, Mechanism, Product distribution Ishiguro, Katsuya; Tomizawa, Kohtaro; Sawaki, Yasuhiko; Iwamura, Hiizu; Tetrahedron Letters; vol. 26; nb. 31; (1985); p. 3723 - 3726 View in Reaxys O O Al

Rx-ID: 2707483 View in Reaxys 541/824 Yield

Conditions & References With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, Time= 4h, T= 25 °C

70 %

Wakamatsu, Kuni; Okuda, Yasuhiro; Oshima, Koichiro; Nozaki, Hitosi; Bulletin of the Chemical Society of Japan; vol. 58; nb. 8; (1985); p. 2425 - 2426 View in Reaxys With copper acetylacetonate, triphenylphosphine, 1.) a) THF, hexane, from -78 deg C to 0 deg C, b) 0 deg C, 10 min, 2.) 0 deg C, 1 h, Yield given. Multistep reaction Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Bulletin of the Chemical Society of Japan; vol. 54; nb. 4; (1981); p. 1281 - 1282 View in Reaxys

O Cl O

Rx-ID: 3695468 View in Reaxys 542/824 Yield

Conditions & References in methanol, Time= 15h, Irradiation Bergmark, William R.; Barnes, Curtis; Clark, Jeffrey; Paparian, Seth; Marynowski, Susan; Journal of Organic Chemistry; vol. 50; nb. 26; (1985); p. 5612 - 5615

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View in Reaxys

O HO

Rx-ID: 3952120 View in Reaxys 543/824 Yield

Conditions & References

10 %, 17 %, With triphenylphosphine, bis-triphenylphosphine-palladium(II) chloride in 1,2-dimethoxyethane, toluene, Time= 20h, T= 50 °C 61 % Wakita, Yoshiaki; Yasunaga, Tomoyuki; Kojima, Masaharu; Journal of Organometallic Chemistry; vol. 288; (1985); p. 261 268 View in Reaxys 25 %, 45 %, With triphenylphosphine, bis-triphenylphosphine-palladium(II) chloride in 1,2-dimethoxyethane, toluene, Time= 25h, T= 50 30 % °C , different quantity of the aluminum reagent; further aluminum reagent, Product distribution Wakita, Yoshiaki; Yasunaga, Tomoyuki; Kojima, Masaharu; Journal of Organometallic Chemistry; vol. 288; (1985); p. 261 268 View in Reaxys O

Rx-ID: 3952122 View in Reaxys 544/824 Yield

Conditions & References

79 %

With triphenylphosphine, bis-triphenylphosphine-palladium(II) chloride in 1,2-dimethoxyethane, hexane, Time= 15h, T= 50 °C Wakita, Yoshiaki; Yasunaga, Tomoyuki; Kojima, Masaharu; Journal of Organometallic Chemistry; vol. 288; (1985); p. 261 268 View in Reaxys

Zn(CN)2

Rx-ID: 18515850 View in Reaxys 545/824 Yield

Conditions & References Reaction Steps: 2 1: 90 percent / tert-butyl hypochlorite, p-toluenesulfonic acid / CCl4 / 0.5 h / Heating 2: methanol / 15 h / Irradiation With tert-butylhypochlorite, toluene-4-sulfonic acid in methanol, tetrachloromethane Bergmark, William R.; Barnes, Curtis; Clark, Jeffrey; Paparian, Seth; Marynowski, Susan; Journal of Organic Chemistry; vol. 50; nb. 26; (1985); p. 5612 - 5615 View in Reaxys

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ZnCl2

Rx-ID: 19037962 View in Reaxys 546/824 Yield

Conditions & References Reaction Steps: 2 1: 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 2.) -78 to 20 deg C 2: aq. AcOH / 24 h / 20 °C With n-butyllithium, acetic acid in tetrahydrofuran, hexane Jazouli, Mustapha El; Masson, Serge; Thuillier, Andre; Journal of the Chemical Society, Chemical Communications; nb. 22; (1985); p. 1598 - 1599 View in Reaxys

HO O

Rx-ID: 1576241 View in Reaxys 547/824 Yield

Conditions & References With iron pentacarbonyl in methanol, Time= 5h, Ambient temperature, Irradiation, Yield given. Yields of byproduct given Nitta, Makoto; Kobayashi, Tomoshige; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1984); p. 2103 - 2108 View in Reaxys O O

HO N O

Rx-ID: 1587628 View in Reaxys 548/824 Yield 41 % Chromat., 54 % Chromat.

Conditions & References With oxygen, thiamine diphosphate in benzene, Time= 0.5h, T= 20 °C , Irradiation Sawaki, Yasuhiko; Ishiguro, Katsuya; Tetrahedron Letters; vol. 25; nb. 14; (1984); p. 1487 - 1490 View in Reaxys

HO N N

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O O

Rx-ID: 1587629 View in Reaxys 549/824 Yield

Conditions & References

4 % Chromat., 5 % Chromat., 30 % Chromat., 35 % Chromat.

Time= 0.25h, T= 0 °C , Irradiation, Rose Bengal Sawaki, Yasuhiko; Ishiguro, Katsuya; Tetrahedron Letters; vol. 25; nb. 14; (1984); p. 1487 - 1490 View in Reaxys

N O

Rx-ID: 1701922 View in Reaxys 550/824 Yield

N Mg Br

Rx-ID: 1745312 View in Reaxys 551/824 Yield

Conditions & References

80 %

in tetrahydrofuran, T= 0 °C Wattanasin, S.; Kathawala, F.G.; Tetrahedron Letters; vol. 25; nb. 8; (1984); p. 811 - 814 View in Reaxys N

N N

O Si

Rx-ID: 1817084 View in Reaxys 552/824 Yield 46 % Spectr., 40 % Spectr.

Conditions & References With tris-(2-chloro-ethyl)-amine, titanium tetrachloride in dichloromethane, Time= 17h, Ambient temperature, without catalyst Hassner, Alfred; Fibiger, Richard; Andisik, Donald; Journal of Organic Chemistry; vol. 49; nb. 22; (1984); p. 4237 - 4244

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View in Reaxys

O O

Rx-ID: 1839913 View in Reaxys 553/824 Yield

Conditions & References With ammonium peroxydisulfate, copper diacetate, sodium acetate in water, acetic acid, T= 100 °C , Yield given. Yields of byproduct given Walling, Cheves; El-Taliawi, Gamil M.; Amarnath, Kalyani; Journal of the American Chemical Society; vol. 106; (1984); p. 7573 - 7578 View in Reaxys O

Rx-ID: 2033907 View in Reaxys 554/824 Yield

Conditions & References With sulfur dioxide, T= -261.2 °C , Irradiation, investigation of photoadducts; η > 300 nm, Mechanism Dunkin, Ian R.; MacDonald, J. Gavin; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1984); p. 2079 - 2084 View in Reaxys O

N O

Rx-ID: 2136162 View in Reaxys 555/824 Yield 65.7 %

Conditions & References in diethyl ether, Irradiation, Further byproducts given Fuhrmann, J.; Haupt, M.; Henning, H.-G.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 2; (1984); p. 177 - 186 View in Reaxys

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O OH

Rx-ID: 2544923 View in Reaxys 556/824 Yield

Conditions & References

16 %, 12 % Chromat.

in acetonitrile, Time= 26h, Irradiation, high-pressure mercury lamp Yoshioka; Suzuki; Oka; Bulletin of the Chemical Society of Japan; vol. 57; nb. 6; (1984); p. 1604 - 1607 View in Reaxys

16 % Chromat., 12 % Chromat.

in acetonitrile, Time= 26h, Irradiation, high-pressure mercury lamp Yoshioka; Suzuki; Oka; Bulletin of the Chemical Society of Japan; vol. 57; nb. 6; (1984); p. 1604 - 1607 View in Reaxys O

N N

Rx-ID: 2549818 View in Reaxys 557/824 Yield

Conditions & References

46 % Chromat., 3.3 % Chromat., 41 % Chromat.

With oxygen in benzene, Time= 6h, T= 20 °C , Irradiation Sawaki, Yasuhiko; Ishiguro, Katsuya; Tetrahedron Letters; vol. 25; nb. 14; (1984); p. 1487 - 1490 View in Reaxys

Rx-ID: 2549819 View in Reaxys 558/824 Yield

Conditions & References

43 % Chromat., 2.6 % Chromat., 96 % Chromat.

With η,η,η,η-Tetraphenylporphin-Zink, oxygen, dimethyl sulfoxide in benzene, Time= 0.0833333h, T= 20 °C , Irradiation Sawaki, Yasuhiko; Ishiguro, Katsuya; Tetrahedron Letters; vol. 25; nb. 14; (1984); p. 1487 - 1490 View in Reaxys

N N

Rx-ID: 2549820 View in Reaxys 559/824 Yield

Conditions & References

6.9 % Chro- With oxygen, thiamine diphosphate in benzene, Time= 0.5h, Irradiation mat., 90 % Chromat., 1 Sawaki, Yasuhiko; Ishiguro, Katsuya; Tetrahedron Letters; vol. 25; nb. 14; (1984); p. 1487 - 1490 % Chromat. View in Reaxys

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H N

O NH 2

NH 2

Rx-ID: 2925122 View in Reaxys 560/824 Yield

Conditions & References in diethyl ether, T= -78 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Czarnocki, Zbigniew; Wrobel, Jerzy T.; Bulletin of the Polish Academy of Sciences, Chemistry; vol. 32; nb. 9-10; (1984); p. 335 - 338 View in Reaxys O OH

N O

Cl N

O O

N HO

Rx-ID: 3151211 View in Reaxys 561/824 Yield 63 %

Rx-ID: 3255340 View in Reaxys 562/824 Yield

Conditions & References in benzene, Time= 5h, Irradiation, high-pressure mercury lamp, Product distribution Yoshioka; Suzuki; Oka; Bulletin of the Chemical Society of Japan; vol. 57; nb. 6; (1984); p. 1604 - 1607 View in Reaxys

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O N O

Br OH

O O

Br N

Rx-ID: 3269188 View in Reaxys 563/824 Yield

Conditions & References

58.3 %

in diethyl ether, Irradiation, Further byproducts given Fuhrmann, J.; Haupt, M.; Henning, H.-G.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 2; (1984); p. 177 - 186 View in Reaxys

O S N

Rx-ID: 3487694 View in Reaxys 564/824 Yield

Conditions & References

33.5 %

in diethyl ether, Irradiation, Further byproducts given Fuhrmann, J.; Haupt, M.; Henning, H.-G.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 2; (1984); p. 177 - 186 View in Reaxys

N H

Rx-ID: 4291697 View in Reaxys 565/824 Yield 97 %

Conditions & References With potassium hydroxide in 1,4-dioxane, methanol, water, Time= 22h, Heating

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Laurent, Andre; Mison, Pierre; Nafti, Abdelhafid; Ben Cheikh, Ridha; Chaabouni, Rifaat; Journal of Chemical Research, Miniprint; nb. 11; (1984); p. 3165 - 3194 View in Reaxys O O

O 5-benzoyl-O 1,O 2-isopropyliden-η-D-arabinofuranose Cl

Rx-ID: 21508078 View in Reaxys 566/824 Yield

Conditions & References Reaction Steps: 2 1: triethylamine / petroleum ether / 0.75 h / 0 °C 2: 80 percent / tetrahydrofuran / 0 °C With triethylamine in tetrahydrofuran, Petroleum ether Wattanasin, S.; Kathawala, F.G.; Tetrahedron Letters; vol. 25; nb. 8; (1984); p. 811 - 814 View in Reaxys O Cl

Rx-ID: 1548751 View in Reaxys 567/824 Yield

Conditions & References

76 % Chro- With hydrogenchloride, zinc(II) chloride in dichloromethane, Time= 1h, Ambient temperature, Product distribution, Mechanism mat., 23 % Chromat., 1 Hanack, Michael; Weber, Erhard; Chemische Berichte; vol. 116; nb. 2; (1983); p. 777 - 797 % Chromat. View in Reaxys

Rx-ID: 1737983 View in Reaxys 568/824 Yield

Conditions & References

21 %, 17 %, With iron pentacarbonyl in methanol, Time= 5h, Irradiation, Further byproducts given 45 % Nitta, Makoto; Kobayashi, Tomoshige; Chemistry Letters; (1983); p. 51 - 54 View in Reaxys O O

Rx-ID: 2005254 View in Reaxys 569/824 Yield 3 % Chromat., 3 % Chromat., 1 % Chro-

Conditions & References With chromyl nitrate in tetrachloromethane, dichloromethane, N,N-dimethyl-formamide, Time= 1h, T= -78 °C , Title compound not separated from byproducts Miyaura, N.; Kochi, J. K.; Journal of the American Chemical Society; vol. 105; nb. 8; (1983); p. 2368 - 2378 View in Reaxys

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mat., 73 % Chromat.

O S O

Rx-ID: 2153612 View in Reaxys 570/824 Yield

Conditions & References With n-butyllithium, bis-trimethylsilanyl peroxide, 1.) THF, -78 deg C; 15 min; 2.) room temp., Yield given. Multistep reaction Hwu, Jih Ru; Journal of Organic Chemistry; vol. 48; nb. 23; (1983); p. 4432 - 4433 View in Reaxys

O HO

Si Si

Rx-ID: 2182345 View in Reaxys 571/824 Yield

Conditions & References With 2<HRh(CO)(PPh3)>, 2-trimethylsilyl-1-phenyl-2-propen-1-one in benzene, Time= 20h, T= 105 Â°C , in sealed tube, Yield given. Yields of byproduct given Matsuda, Isamu; Sato, Susumu; Izumi, Yusuke; Tetrahedron Letters; vol. 24; nb. 27; (1983); p. 2787 - 2790 View in Reaxys O HO

HO O

Rx-ID: 2970742 View in Reaxys 572/824 Yield

Conditions & References With sodium persulfate, sulfuric acid, silver nitrate, copper(II) sulfate, 1.) water, reflux, 2.) 5 min, reflux, Yield given. Multistep reaction. Yields of byproduct given Fristad, William E.; Fry, Melisa A.; Klang, Jeffrey A.; Journal of Organic Chemistry; vol. 48; nb. 20; (1983); p. 3575 - 3577 View in Reaxys

O O

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O 2H

Rx-ID: 3135579 View in Reaxys 573/824 Yield

Conditions & References With titanium tetrachloride, T= -30 - -20 °C , Product distribution Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys

Rx-ID: 3195518 View in Reaxys 574/824 Yield

Conditions & References T= 160 °C , influence of catalyst nature, temperature, Rate constant, Mechanism, Product distribution Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys

O O

Rx-ID: 3195519 View in Reaxys 575/824 Yield

Conditions & References With iron(II) sulfate in tetrahydrofuran, Time= 2h, Ambient temperature Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys

Rx-ID: 3195521 View in Reaxys 576/824

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Yield

Conditions & References T= 160 °C , influence of the catalyst nature, temperature, Rate constant, Mechanism, Product distribution Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys O O

Rx-ID: 3405104 View in Reaxys 577/824 Yield

Conditions & References With lithium methyl(cyano)cuprate in diethyl ether, N,N-dimethyl-formamide, var. substrates ratio, var. temp.; other bromoketones; other cuprates; also in the presence of chelating agents Hamon, Louis; Levisalles, Jacques; Journal of Organometallic Chemistry; vol. 253; nb. 2; (1983); p. 259 - 272 View in Reaxys O O

O O

Rx-ID: 3842779 View in Reaxys 578/824 Yield 1 % Chromat., 6 % Chromat., 2 % Chromat., 40 % Chromat., 22 % Chromat.

Conditions & References With sodium hydroxide, ethylenediaminetetraacetic acid, dihydrogen peroxide in water, Time= 10h, T= 25 °C , mechanism; energy data: ΔH(excit.), ΔS(excit.); other electron deficient acetylenes and related compounds, other alcohol, var. temp. and reagent ratio, Kinetics, Rate constant, Product distribution Sawaki; Inoue; Ogata; Bulletin of the Chemical Society of Japan; vol. 56; nb. 4; (1983); p. 1133 - 1138 View in Reaxys

O O I

biscyclopentadienyl titanium-μ-chloro-μmethylidene bismethyl aluminum

Rx-ID: 5931092 View in Reaxys 579/824 Yield

Conditions & References Multistep reaction Chou, Ta-Shue; Huang, Sung-Ben; Tetrahedron Letters; vol. 24; nb. 21; (1983); p. 2169 - 2170 View in Reaxys

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O O

O S

(CO)4FeC(OLi)(C6H5)

Rx-ID: 7446348 View in Reaxys 580/824 Yield

Conditions & References With iron(III) chloride in N,N,N,N,N,N-hexamethylphosphoric triamide, diethyl ether, - 78 deg C, 4 h -> 25 deg C; other solvents, Yield given. Yields of byproduct given Semmelhack, M. F.; Tamura, Rui; Journal of the American Chemical Society; vol. 105; nb. 12; (1983); p. 4099 - 4100 View in Reaxys O

(CO)4FeC(OLi)(C6H5)

Rx-ID: 7446349 View in Reaxys 581/824 Yield

Conditions & References With iron(III) chloride in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 24h, T= 25 °C , Yield given. Yields of byproduct given Semmelhack, M. F.; Tamura, Rui; Journal of the American Chemical Society; vol. 105; nb. 12; (1983); p. 4099 - 4100 View in Reaxys

O O

(CO)4FeC(OLi)(C6H5)

S O

Rx-ID: 7446350 View in Reaxys 582/824 Yield

Conditions & References With iron(III) chloride in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 18h, T= 65 °C , Yield given. Yields of byproduct given Semmelhack, M. F.; Tamura, Rui; Journal of the American Chemical Society; vol. 105; nb. 12; (1983); p. 4099 - 4100 View in Reaxys O

O S

(CO)4FeC(ONMe4)(C6H5) O

Rx-ID: 7446351 View in Reaxys 583/824

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Yield

Conditions & References With iron(III) chloride in dichloromethane, - 78 deg C, 4 h -> 25 deg C; other solvents, Yield given. Yields of byproduct given Semmelhack, M. F.; Tamura, Rui; Journal of the American Chemical Society; vol. 105; nb. 12; (1983); p. 4099 - 4100 View in Reaxys O HO

ZnCl2

N O

Rx-ID: 19451115 View in Reaxys 584/824 Yield

Conditions & References Reaction Steps: 2 1: 68 percent / sodium dichromate, H2SO4(conc.) / H2O / Ambient temperature 2: 58 percent / BNAH / hexamethylphosphoric acid triamide / 48 h / Ambient temperature; Irradiation With sodium dichromate, 1-Benzyl-1,4-dihydronicotinamide, sulfuric acid in N,N,N,N,N,N-hexamethylphosphoric triamide, water Ono; Tamura; Kaji; Journal of the American Chemical Society; vol. 105; nb. 12; (1983); p. 4017 - 4022 View in Reaxys O

platinum

Rx-ID: 19883851 View in Reaxys 585/824 Yield

Conditions & References Reaction Steps: 2 1: boron trifluoride-diethyl ether / CH2Cl2 / 0.33 h / 0 °C 2: FeSO4*7H2O / tetrahydrofuran / 2 h / Ambient temperature With boron trifluoride diethyl etherate, iron(II) sulfate in tetrahydrofuran, dichloromethane Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys Reaction Steps: 2 1: boron trifluoride-diethyl ether / CH2Cl2 / 0.33 h / 0 °C 2: FeSO4*7H2O / tetrahydrofuran / 2 h / Ambient temperature With boron trifluoride diethyl etherate, iron(II) sulfate in tetrahydrofuran, dichloromethane Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys O

Br–

+Mg

Rx-ID: 21269344 View in Reaxys 586/824 Yield

Conditions & References Reaction Steps: 2 1: 1.) magnesium bromide etherate, 2.) Li / 1.) ether, 5 h, 2.) 17 h 2: 70 percent / 12.5 h / 220 - 225 °C With lithium, magnesium bromide ethyl etherate Barluenga, Jose; Florez, Josefa; Yus, Miguel; Synthesis; nb. 8; (1983); p. 647 - 649

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View in Reaxys Reaction Steps: 3 1: Eintragen unter Kuehlung 2: KOH 3: 300 °C With potassium hydroxide Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys Reaction Steps: 3 1: Eintragen unter Kuehlung 2: KOH 3: 300 °C With potassium hydroxide Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys O

Rx-ID: 25117644 View in Reaxys 587/824 Yield

Conditions & References 5 : EXAMPLE 5 EXAMPLE 5 0.5 liter per hour of a mixture of acetophenone and a 30percent strength solution of formaldehyde in isobutanol (the molar ratio of acetophenone to formaldehyde being 8:1) was reacted at 180° C., under 30 bar H2 pressure, in the apparatus, and over the catalyst, described in Example 1. The yield of propiophenone obtained was 52.8percent, based on formaldehyde employed. With formaldehyd in 2-methyl-propan-1-ol Patent; BASF Aktiengesellschaft; US4374274; (1983); (A) English View in Reaxys O N

(v4)

Ni (v4)

N (v4)

O N

(v4) N (v4) Ni 2+ (v4) (v4) (v2) CH –2O–

Rx-ID: 26410156 View in Reaxys 588/824 Yield 6 %, 30 %, 36 %, 10 %

Conditions & References in tetrahydrofuran, mixt. of educts in THF stirred at room temp. for 24 h; IR and GLC anal. Yamamoto, Takakazu; Kohara, Teiji; Osakada, Kohtaro; Yamamoto, Akio; Bulletin of the Chemical Society of Japan; vol. 56; nb. 7; (1983); p. 2147 - 2153 ; (from Gmelin) View in Reaxys

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O O Cl Al O Cl

Rx-ID: 1776707 View in Reaxys 589/824 Yield

Conditions & References

81 %

in dichloromethane, 1) -50 deg c, 30 min; 2) 20 deg C, 2 - 3 h Tolstikov, G. A.; Valitov, F. Kh.; Kuchin, A. V.; Doklady Chemistry; vol. 265; (1982); p. 291 - 293; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 265; nb. 6; (1982); p. 1406 - 1410 View in Reaxys

Cl Al

Cl N

Rx-ID: 1840047 View in Reaxys 590/824 Yield

Conditions & References

68 %

in dichloromethane, Time= 3h, T= 20 °C Tolstikov, G. A.; Valitov, F. Kh.; Kuchin, A. V.; Doklady Chemistry; vol. 265; (1982); p. 291 - 293; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 265; nb. 6; (1982); p. 1406 - 1410 View in Reaxys

Cl Al

N N

Rx-ID: 1970499 View in Reaxys 591/824 Yield

Conditions & References

73 %

Rx-ID: 1985354 View in Reaxys 592/824 Yield

Conditions & References With hydrogen selenide, triethylamine in methanol, Time= 3h, Ambient temperature, Yield given Asinger, Friedrich; Schmitz, Maria Karoline; Monatshefte fuer Chemie; vol. 113; (1982); p. 1191 - 1212 View in Reaxys

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O Cl Al

O Cl

Rx-ID: 2024681 View in Reaxys 593/824 Yield

Conditions & References

86 %

in dichloromethane, added at -70 deg C, then 8 h at room temperature. AlCl3 can be added as well. Tolstikov, G. A.; Valitov, F. Kh.; Kuchin, A. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 6; (1982); p. 1328 1334,1170 - 1175 View in Reaxys O

Rx-ID: 2034222 View in Reaxys 594/824 Yield

Conditions & References With hydrogenchloride in water, Time= 0.5h, Ambient temperature, Yield given Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys O

HO O P O

Rx-ID: 2156117 View in Reaxys 595/824 Yield

Conditions & References

84 %

With tributyltin methoxide in toluene, Time= 0.5h, Heating Sekine, Mitsuo; Kume, Akiko; Hata, Tsujiaki; Journal of the Chemical Society, Chemical Communications; nb. 18; (1981); p. 969 - 970 View in Reaxys With sodium hydroxide in ethanol, Time= 0.0833333h, Yield given Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys O O

Rx-ID: 2157447 View in Reaxys 596/824 Yield

Conditions & References With hydrogen selenide, triethylamine in methanol, Time= 1h, T= -10 Â°C , Yield given

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Asinger, Friedrich; Schmitz, Maria Karoline; Monatshefte fuer Chemie; vol. 113; (1982); p. 1191 - 1212 View in Reaxys O

Rx-ID: 2157678 View in Reaxys 597/824 Yield

Conditions & References in 1,4-dioxane, water, T= 30 °C , Equilibrium constant Krishnan, Kp.; Chandrasekaran, J.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 21; nb. 6; (1982); p. 595 - 597 View in Reaxys O

Rx-ID: 2705452 View in Reaxys 598/824 Yield

Conditions & References

40 %, 23 %

With ethylaluminum dichloride in dichloromethane, Time= 1h, T= 25 °C Snider, Barry B.; Jackson, Andrew C.; Journal of Organic Chemistry; vol. 47; nb. 27; (1982); p. 5393 - 5395 View in Reaxys O

Cl Al

Rx-ID: 2707954 View in Reaxys 599/824 Yield

Conditions & References

40 %, 23 %

in dichloromethane, Time= 1h, T= 25 °C Snider, Barry B.; Jackson, Andrew C.; Journal of Organic Chemistry; vol. 47; nb. 27; (1982); p. 5393 - 5395 View in Reaxys

H N

Rx-ID: 4077062 View in Reaxys 600/824 Yield 88 %, 4 %

Conditions & References in benzene, Ambient temperature Cook, Lawrence S.; Prudhoe, Gordon; Venayak, Narinder D.; Wakefield, Basil J.; Journal of Chemical Research, Miniprint; nb. 5; (1982); p. 1357 - 1367 View in Reaxys

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H N

Rx-ID: 4078223 View in Reaxys 601/824 Yield

Conditions & References

3 %, 85 %

Time= 0.166667h, T= 250 Â°C Cook, Lawrence S.; Prudhoe, Gordon; Venayak, Narinder D.; Wakefield, Basil J.; Journal of Chemical Research, Miniprint; nb. 5; (1982); p. 1357 - 1367 View in Reaxys

Si O O

ZnCl2

P O

Rx-ID: 19026256 View in Reaxys 602/824 Yield

Conditions & References Reaction Steps: 3 1: 1.) LDA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, hexane, -78 deg C, 0.7 h 2: p-toluenesulfonic acid / methanol; H2O / 1.5 h / Heating 3: 1 M NaOH / ethanol / 0.08 h With sodium hydroxide, toluene-4-sulfonic acid, lithium diisopropyl amide in methanol, ethanol, water Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys O

ZnCl2

oxygen O

Rx-ID: 19036002 View in Reaxys 603/824 Yield

Conditions & References Reaction Steps: 4 1: 91 percent / benzene / 6 h / Ambient temperature 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, hexane, -78 deg C, 0.7 h

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3: p-toluenesulfonic acid / methanol; H2O / 1.5 h / Heating 4: 1 M NaOH / ethanol / 0.08 h With sodium hydroxide, toluene-4-sulfonic acid, lithium diisopropyl amide in methanol, ethanol, water, benzene Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys Reaction Steps: 4 1: 1.) Na 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, hexane, -78 deg C, 0.7 h 3: p-toluenesulfonic acid / methanol; H2O / 1.5 h / Heating 4: 1 M NaOH / ethanol / 0.08 h With sodium hydroxide, sodium, toluene-4-sulfonic acid, lithium diisopropyl amide in methanol, ethanol, water Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys

O O

ZnCl2

O P O

Rx-ID: 19049805 View in Reaxys 604/824 Yield

Conditions & References Reaction Steps: 2 1: p-toluenesulfonic acid / methanol; H2O / 1.5 h / Heating 2: 1 M NaOH / ethanol / 0.08 h With sodium hydroxide, toluene-4-sulfonic acid in methanol, ethanol, water Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys O O

ZnCl2

Rx-ID: 19191000 View in Reaxys 605/824 Yield

Conditions & References Reaction Steps: 2 1: 89 percent / NaHS / methanol; diethyl ether / 4 h / -20 °C 2: H2Se(gas), Et3N / methanol / 1 h / -10 °C With sodium hydrogensulfide, hydrogen selenide, triethylamine in methanol, diethyl ether Asinger, Friedrich; Schmitz, Maria Karoline; Monatshefte fuer Chemie; vol. 113; (1982); p. 1191 - 1212 View in Reaxys O

platinum

Rx-ID: 19970061 View in Reaxys 606/824

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Yield

Conditions & References Reaction Steps: 3 1: 1.) Br2 2.) n-butyllithium / 1.) THF, ; 2.) ether, -70 deg C, 30 min 2: tetrahydrofuran / 0.5 h / -65 °C 3: 1.2 N HCl / H2O / 0.5 h / Ambient temperature With hydrogenchloride, n-butyllithium, bromine in tetrahydrofuran, water Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys Reaction Steps: 4 1: 1.) Br2 2.) triethylamine / 1.) ether, -60 deg C, 0.5 h then 0 deg C; 2.) ether, -20 deg C 2: 100 percent / n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -70 °C 3: tetrahydrofuran / 0.5 h / -65 °C 4: 1.2 N HCl / H2O / 0.5 h / Ambient temperature With hydrogenchloride, n-butyllithium, bromine, triethylamine in tetrahydrofuran, diethyl ether, water Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys Li

platinum N

Rx-ID: 19978135 View in Reaxys 607/824 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 0.5 h / -65 °C 2: 1.2 N HCl / H2O / 0.5 h / Ambient temperature With hydrogenchloride in tetrahydrofuran, water Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys Br

platinum N

Rx-ID: 19978140 View in Reaxys 608/824 Yield

Conditions & References Reaction Steps: 3 1: 100 percent / n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -70 °C 2: tetrahydrofuran / 0.5 h / -65 °C 3: 1.2 N HCl / H2O / 0.5 h / Ambient temperature With hydrogenchloride, n-butyllithium in tetrahydrofuran, diethyl ether, water Duhamel, Lucette; Poirier, Jean-Marie; Bulletin de la Societe Chimique de France; vol. 2; nb. 9-10; (1982); p. 297 - 303 View in Reaxys

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O O

O Pb O

O O

Rx-ID: 26943764 View in Reaxys 609/824 Yield

Conditions & References

32.4 %, <1, 1 %, 62 %, 6.8 %

With trifluoroacetic acid, benzene in trifluoroacetic acid, dissolution of lead compd. and benzene in CF3COOH, keeping for 24 h; removal of CF3COOH by means of a stream of dry N2, addn. of acetone, monitoring by GLC analysis Bell, H. Craig; Pinhey, John T.; Sternhell, Sever; Australian Journal of Chemistry; vol. 35; (1982); p. 2237 - 2246 ; (from Gmelin) View in Reaxys

O O

O Pb O

O O O

O O

Rx-ID: 26943765 View in Reaxys 610/824 Yield

Conditions & References

<1, 1 %, 63 %, 70 %, 13.8 %

With trifluoroacetic acid, 1,3,5-trimethyl-benzene in trifluoroacetic acid, dissolution of lead compd. and mesitylene in CF3COOH, keeping for 24 h; removal of CF3COOH by means of a stream of dry N2, addn. of acetone, monitoring by GLC analysis Bell, H. Craig; Pinhey, John T.; Sternhell, Sever; Australian Journal of Chemistry; vol. 35; (1982); p. 2237 - 2246 ; (from Gmelin) View in Reaxys

O Pb O

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O O

Rx-ID: 26943766 View in Reaxys 611/824 Yield

Conditions & References

1 %, 2 %, 12.6 %, 8.4 %

With trifluoroacetic acid in trifluoroacetic acid, dissolution of lead compd. in CF3COOH, keeping for 24 h; removal of CF3COOH by means of a stream of dry N2, addn. of acetone, monitoring by GLC analysis Bell, H. Craig; Pinhey, John T.; Sternhell, Sever; Australian Journal of Chemistry; vol. 35; (1982); p. 2237 - 2246 ; (from Gmelin) View in Reaxys

O O

O Pb O

O O

Rx-ID: 26943767 View in Reaxys 612/824 Yield

Conditions & References

15 %, 20 %, With methoxybenzene, trifluoroacetic acid in trifluoroacetic acid, dissolution of lead compd. and anisole in CF3COOH, keeping 13.3 % for 24 h; removal of CF3COOH by means of a stream of dry N2, addn. of acetone, monitoring by GLC analysis Bell, H. Craig; Pinhey, John T.; Sternhell, Sever; Australian Journal of Chemistry; vol. 35; (1982); p. 2237 - 2246 ; (from Gmelin) View in Reaxys O HO

Rx-ID: 1763984 View in Reaxys 613/824 Yield

Conditions & References With air, tetrabutylammonium borohydride, (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, 1) CH2Cl2, 2) CH2Cl2, r.t., 24 h, Yield given. Multistep reaction. Yields of byproduct given Perree-Fauvet, M.; Gaudemer, A.; Journal of the Chemical Society, Chemical Communications; nb. 17; (1981); p. 874 - 875 View in Reaxys O

O O

Rx-ID: 2007967 View in Reaxys 614/824 Yield 16.5 %, 65 %

Conditions & References With Marshall's acid, copper(II) sulfate in acetic acid, Time= 4h, T= 80 - 85 Â°C Perumal, P. Thirumalai; Bhatt, M. Vivekananda; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 20; nb. 2; (1981); p. 153 - 155 View in Reaxys

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O O HO

Rx-ID: 2015389 View in Reaxys 615/824 Yield

Conditions & References in benzene, Time= 24h, Irradiation, Yield given. Yields of byproduct given Berti, Corrado; Greci, Lucedio; Synthetic Communications; vol. 11; nb. 9; (1981); p. 681 - 686 View in Reaxys O O Al

Rx-ID: 2069270 View in Reaxys 616/824 Yield

Conditions & References With copper acetylacetonate, triphenylphosphine, 1.) a) THF, hexane, from -78 deg C to 0 deg C, b) 0 deg C, 10 min, 2.) 0 deg C, 1 h, Yield given. Multistep reaction Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Bulletin of the Chemical Society of Japan; vol. 54; nb. 4; (1981); p. 1281 - 1282 View in Reaxys O

Rx-ID: 2188673 View in Reaxys 617/824 Yield

Conditions & References

15.0 % Chromat., 70.5 % Chromat.

With sodium tetrahydroborate in methanol, Time= 3h, Ambient temperature Nishio, Takehiko; Omote, Yoshimori; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 934 - 938 View in Reaxys

15.0 % Chromat., 70.5 % Chromat.

With sodium tetrahydroborate in methanol, Time= 3h, Ambient temperature, other metal halide, reagents ratio, Product distribution Nishio, Takehiko; Omote, Yoshimori; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 934 - 938 View in Reaxys -1

-1 F

-1

(v4)

B FF

F 2

(v4)

B FF

F B

(v4)

O+

F S+

S+

Rx-ID: 2282645 View in Reaxys 618/824 Yield

Conditions & References With water in dichloromethane, Time= 0.583333h, Yield given Stahl, Ingfried; Synthesis; nb. 2; (1981); p. 135 - 137 View in Reaxys

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Rx-ID: 2651709 View in Reaxys 619/824 Yield

Conditions & References

65 %

With oxalyl dichloride, triethylamine, -60 deg C; 1.) DMSO, CH2Cl2, 15 min; 2.) 5 min, Yield given. Multistep reaction Barluenga, J.; Gomez, N.; Palacios, F.; Gotor, V.; Synthesis; nb. 7; (1981); p. 563 - 565 View in Reaxys

65 %, 35 %

With oxalyl dichloride, dimethyl sulfoxide, triethylamine in dichloromethane, Time= 0.333333h, T= -60 °C Smith, Amos B.; Levenberg, Patricia A.; Synthesis; nb. 7; (1981); p. 567 - 570 View in Reaxys O O

Rx-ID: 2880466 View in Reaxys 620/824 Yield

Conditions & References

60 %

With silver carbonate, Time= 6h, T= 110 °C Ishino, Yoshio; Nishiguchi, Ikuzo; Nakao, Satoshi; Hirashima, Tsuneaki; Chemistry Letters; (1981); p. 641 - 644 View in Reaxys O O

Na + O

O–

O S O

Rx-ID: 3545471 View in Reaxys 621/824 Yield

Conditions & References in N,N,N,N,N,N-hexamethylphosphoric triamide, Product distribution Gompper, Rudolf; Vogt, Hans-Hubert; Wagner, Hans-Ulrich; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 36; nb. 12; (1981); p. 1644 - 1652 View in Reaxys O

N O

Rx-ID: 3933606 View in Reaxys 622/824 Yield

Conditions & References hydrolysis Padwa, Albert; Akiba, Mitsuo; Cohen, Leslie A.; MacDonald, J. Gavin; Tetrahedron Letters; vol. 22; nb. 26; (1981); p. 2435 - 2438 View in Reaxys

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ammonium carbonate

platinum

Rx-ID: 20541801 View in Reaxys 623/824 Yield

Conditions & References Reaction Steps: 2 1: sodium methoxide / diethyl ether / 5 h / 0 °C 2: 70.5 percent Chromat. / NaBH4, CoCl2 / methanol / 3 h / Ambient temperature; other metal halide, reagents ratio With sodium tetrahydroborate, sodium methylate in methanol, diethyl ether Nishio, Takehiko; Omote, Yoshimori; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 934 - 938 View in Reaxys

HO O O

O O Sn

P O

Rx-ID: 26169939 View in Reaxys 624/824 Yield

Conditions & References

84 %

in toluene, reflux for 30 min Sekine, Mitsuo; Kume, Akiko; Hata, Tsujiaki; Journal of the Chemical Society, Chemical Communications; nb. 18; (1981); p. 969 - 970 ; (from Gmelin) View in Reaxys vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.1.1, page 38 - 56 ; (from Gmelin) View in Reaxys –

O Hg 2+

O O O O O

Rx-ID: 1548674 View in Reaxys 625/824 Yield

Conditions & References With sodium tetrahydroborate, 1.) acetic acid, 60 deg C, 5 h, 2.) aq. THF, 0 deg C , 1 h, Yield given. Multistep reaction. Yields of byproduct given Uemura, Sakae; Miyoshi, Haruo; Okano, Masaya; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1980); p. 1098 - 1103 View in Reaxys

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â&#x20AC;&#x201C;O

Hg 2+

O O

Rx-ID: 1548675 View in Reaxys 626/824 Yield

Conditions & References 1.) acetic acid, 60 deg C, 5 h, 2.) reflux, 1 h, Yield given. Multistep reaction. Yields of byproduct given Uemura, Sakae; Miyoshi, Haruo; Okano, Masaya; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1980); p. 1098 - 1103 View in Reaxys O

O O O O

Rx-ID: 1548753 View in Reaxys 627/824 Yield

Conditions & References With sodium tetrahydroborate, mercury(II) diacetate, 1.) acetic acid, 60 deg C, 5 h, 2.) aq. THF, 0 deg C , 1 h, Yield given. Multistep reaction. Yields of byproduct given Uemura, Sakae; Miyoshi, Haruo; Okano, Masaya; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1980); p. 1098 - 1103 View in Reaxys

O O

Rx-ID: 1548755 View in Reaxys 628/824 Yield

Conditions & References With mercury(II) diacetate, 1.) acetic acid, 60 deg C, 5 h, 2.) reflux, 1 h, Yield given. Multistep reaction. Yields of byproduct given Uemura, Sakae; Miyoshi, Haruo; Okano, Masaya; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1980); p. 1098 - 1103 View in Reaxys HO

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O H

Rx-ID: 1764003 View in Reaxys 629/824 Yield 3.4 %, 26.9 %, 3.2 %, 2.9 %, 0.8 %, 55.1 %

Conditions & References With 2,2'-azobis(isobutyronitrile), oxygen in chlorobenzene, T= 120 °C , p= 759.8Torr , Product distribution, Mechanism Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 View in Reaxys HO H

HO O

O O

Rx-ID: 1764007 View in Reaxys 630/824 Yield 2.7 %, 26.4 %, 2.9 %, 3.2 %, 52.1 %, 0.4 %

Conditions & References With 2,2'-azobis(isobutyronitrile), oxygen in chlorobenzene, T= 100 °C , p= 759.8Torr , Product distribution, Mechanism Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 View in Reaxys

O O

Rx-ID: 1764008 View in Reaxys 631/824 Yield

Conditions & References With O(3P) produced by O2 discharge, Time= 2h, T= -25 °C Zadok, Elazar; Amar, Dan; Mazur, Yehuda; Journal of the American Chemical Society; vol. 102; nb. 20; (1980); p. 6369 6370 View in Reaxys N

O Li

Rx-ID: 1895776 View in Reaxys 632/824 Yield

Conditions & References Yield given. Multistep reaction Hegedus,L.S.; Williams,R.E.; Mcguire,M.A.; Journal of the American Chemical Society; vol. 102; (1980); p. 4973 View in Reaxys

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O H

Rx-ID: 2005268 View in Reaxys 633/824 Yield

Conditions & References

2.2 %, 24.5 %, 1.8 %, 4.0 %, 7.4 %, 32.4 %

With 2,2'-azobis(isobutyronitrile), oxygen in chlorobenzene, T= 120 °C , p= 759.8Torr , Product distribution, Mechanism Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 View in Reaxys

O O

Rx-ID: 2005276 View in Reaxys 634/824 Yield

Rx-ID: 2042724 View in Reaxys 635/824 Yield

Conditions & References With mercury(II) diacetate, lithium carbonate, lithium chloride, palladium dichloride, 1.) MeOH, 20 deg C, 0.5 h, 2.) 38 deg C, 10 h,, Yield given. Multistep reaction. Yields of byproduct given Ryu, Ilhyong; Matsumoto, Koichi; Ando, Masato; Murai, Shinji; Sonoda, Noboru; Tetrahedron Letters; vol. 21; nb. 44; (1980); p. 4283 - 4286 View in Reaxys N N

Rx-ID: 2085237 View in Reaxys 636/824

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Yield

Conditions & References

69 %

in diethyl ether, Ambient temperature, Yields of byproduct given Hassner, Alfred; Belinka, Benjamin A.; Journal of the American Chemical Society; vol. 102; nb. 19; (1980); p. 6185 - 6188 View in Reaxys O

Rx-ID: 2094151 View in Reaxys 637/824 Yield

Conditions & References in benzene, Ambient temperature, Irradiation, laser flash photolysis; other solvents (10:90 water-MeCN, 7percent OP(OPr)3 in benzene), quenching data (Me2C=CHCH=CMe2 as quencher, in MeCN-H2O, MeOH or benzene, Stern-Volmer plots), oxygen effect, Quantum yield, Mechanism Bays, J. P.; Encinas, M. V.; Small, R. D.; Scaiano, J. C.; Journal of the American Chemical Society; vol. 102; nb. 2; (1980); p. 727 - 734 View in Reaxys OH

O O

N N N

Rx-ID: 2185924 View in Reaxys 638/824 Yield

Conditions & References

50 %

With nitrosonium tetrafluoroborate in acetonitrile, Time= 0.0833333h, T= 0 Â°C Lorenzin, Michele; Guerriero, Antonio; Pietra, Francesco; Journal of Organic Chemistry; vol. 45; nb. 9; (1980); p. 1704 1705 View in Reaxys O

Li N

Rx-ID: 2193686 View in Reaxys 639/824 Yield

Conditions & References

32 %

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O O

O O O

Rx-ID: 2447598 View in Reaxys 640/824 Yield

Conditions & References

11 %, 51 %

With ozone in tetrachloromethane, T= -20 °C , Yield given. Further byproducts given Ito, Yoshikatsu; Yokoya, Hiroaki; Umehara, Yasutoshi; Matsuura, Teruo; Bulletin of the Chemical Society of Japan; vol. 53; nb. 8; (1980); p. 2407 - 2408 View in Reaxys O O N

O O

O O O

Rx-ID: 2447599 View in Reaxys 641/824 Yield

Conditions & References

10 %, 51 %

With ozone in tetrachloromethane, T= -20 °C , Further byproducts given Ito, Yoshikatsu; Yokoya, Hiroaki; Umehara, Yasutoshi; Matsuura, Teruo; Bulletin of the Chemical Society of Japan; vol. 53; nb. 8; (1980); p. 2407 - 2408 View in Reaxys O N

N O

O O

O O O

Rx-ID: 2447600 View in Reaxys 642/824 Yield 11 %, 51 %

Conditions & References With ozone in tetrachloromethane, T= -20 °C , Further byproducts given Ito, Yoshikatsu; Yokoya, Hiroaki; Umehara, Yasutoshi; Matsuura, Teruo; Bulletin of the Chemical Society of Japan; vol. 53; nb. 8; (1980); p. 2407 - 2408 View in Reaxys

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O O

Rx-ID: 2577671 View in Reaxys 643/824 Yield

Conditions & References With aqueous acid, Yield given Ager, David J.; Tetrahedron Letters; vol. 21; (1980); p. 4759 - 4762 View in Reaxys

O Cl

O (v2)

H 2N

NH 2

Rx-ID: 2821760 View in Reaxys 644/824 Yield 42 %, 73 %

Conditions & References With aniline, Time= 1h, T= 20 °C Barluenga, Jose; Campos, Pedro J.; Roy, Miguel A.; Asensio, Gregorio; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1420 - 1426 View in Reaxys O O

Rx-ID: 2879607 View in Reaxys 645/824 Yield 75 %, 25 %

Conditions & References With mercury(II) diacetate in acetic acid, Time= 3h, Heating Uemura, Sakae; Miyoshi, Haruo; Okano, Masaya; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1980); p. 1098 - 1103 View in Reaxys O O

Br O

Rx-ID: 2909265 View in Reaxys 646/824 Yield

Conditions & References With iodine, magnesium, triethylamine, benzene or toluene, Et2O, Yield given. Multistep reaction Kikkawa, Ikuo; Yorifuji, Tadahiko; Synthesis; nb. 11; (1980); p. 877 - 880 View in Reaxys

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NH Li N

N H

H N

N H

Rx-ID: 2937302 View in Reaxys 647/824 Yield

Conditions & References

34 %, 11 %, in hexane, Time= 1h, 0 deg C -> room temperature 6 %, 11 % Cook, Lawrence S.; Wakefield, Basil J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 2392 - 2397 View in Reaxys

N O Al

N NH 2 H

N N O

H 2N N

Rx-ID: 2937351 View in Reaxys 648/824

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Yield

Conditions & References With water, multistep reaction, Mechanism Piotrowski, A.; Kunicki, A.; Pasynkiewicz, S.; Journal of Organometallic Chemistry; vol. 201; nb. 1; (1980); p. 105 - 112 View in Reaxys

N O Al

NH 2 H 2N

Rx-ID: 2937354 View in Reaxys 649/824 Yield

Conditions & References With water, Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given Piotrowski, A.; Kunicki, A.; Pasynkiewicz, S.; Journal of Organometallic Chemistry; vol. 201; nb. 1; (1980); p. 105 - 112 View in Reaxys O

C C H

Rx-ID: 2944011 View in Reaxys 650/824 Yield

Conditions & References With 1-hydroxy-4-methyl-5-oxo-1,5-diphenylpentane-1,4-diyl biradical in water, acetonitrile, Ambient temperature, biradical mixture lifetime, Quantum yield, Rate constant Bays, J. P.; Encinas, M. V.; Small, R. D.; Scaiano, J. C.; Journal of the American Chemical Society; vol. 102; nb. 2; (1980); p. 727 - 734 View in Reaxys

O Cl

O H 2N

(v2)

H 2N

NH 2

Rx-ID: 3374391 View in Reaxys 651/824 Yield 42 %, 73 %

Conditions & References Time= 1h, T= 20 Â°C

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Barluenga, Jose; Campos, Pedro J.; Roy, Miguel A.; Asensio, Gregorio; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1420 - 1426 View in Reaxys

O O

O HO

Rx-ID: 3627690 View in Reaxys 652/824 Yield

Conditions & References

4 %, 50 %

in benzene, Time= 87h, T= 155 °C , thermolysis, Product distribution, Mechanism McCullough, Kevin J.; Morgan, Alistair R.; Nonhebel, Derek C.; Pauson, Peter L.; Journal of Chemical Research, Miniprint; nb. 2; (1980); p. 629 - 650 View in Reaxys O

Rx-ID: 3886994 View in Reaxys 653/824 Yield

Conditions & References With lithium diisopropyl amide, 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 1 h, Yield given. Multistep reaction Hase, T. A.; Kukkola, P.; Synthetic Communications; vol. 10; nb. 6; (1980); p. 451 - 456 View in Reaxys O

Rx-ID: 21234934 View in Reaxys 654/824 Yield

Conditions & References Reaction Steps: 2 1: NaN3 / dioxane; H2O / 23 h / Heating 2: nitrosonium tetrafluoroborate / acetonitrile / 0.08 h / 0 °C With sodium azide, nitrosonium tetrafluoroborate in 1,4-dioxane, water, acetonitrile Lorenzin, Michele; Guerriero, Antonio; Pietra, Francesco; Journal of Organic Chemistry; vol. 45; nb. 9; (1980); p. 1704 1705 View in Reaxys

OH O

O Sn

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H H HO

Rx-ID: 26482839 View in Reaxys 655/824 Yield 2 %, 2 %

Conditions & References With di-tert-butyl peroxide in neat (no solvent), addn. of peroxide to equimolar mixt. of (CH2CHCH2)4Sn and PhCHOCH2, 24h, 130Â°C, acidolysis by addn. of malonic acid in ether, reflux, 48h, ether removed, pptn. of malonate by addn. of pentane, under Ar; alcohol detected by chromy., total yield: 30percent Daude, Gerard; Pereyre, Michel; Journal of Organometallic Chemistry; vol. 190; nb. 1; (1980); p. 43 - 52 ; (from Gmelin) View in Reaxys O

Rx-ID: 25333244 View in Reaxys 656/824 Yield

Conditions & References 122 : EXAMPLE 122 The yield of hydratropic aldehyde was 16percent and the yield of phenyl propionaldehyde 35percent based on bromobenzene. Patent; Givaudan Corporation; US4070374; (1978); (A) English View in Reaxys O

(+-)-2.3-dibromo-propylamine hydrobromide Cl

Rx-ID: 22751912 View in Reaxys 657/824 Yield

Conditions & References Reaction Steps: 2 1: (i) benzene, (ii) (electrolysis) 2: aq. HCl / ethanol With hydrogenchloride in ethanol Bestmann,H.J. et al.; Chemische Berichte; vol. 103; (1970); p. 2794 - 2801 View in Reaxys

SnH

(v4)

Sn O

Rx-ID: 26762450 View in Reaxys 658/824

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Yield 57 %, 5-15

Conditions & References in neat (no solvent), in absence of solvent and catalyst; ratio of educts 1:1; at 55°C, for 6 h; contamination of the product by C2H5COC6H5 probably caused by the hydrolysis of the Sn product Leusink; Noltes; Tetrahedron Letters; vol. 7; nb. 20; (1966); p. 2221 - 2225 ; (from Gmelin) View in Reaxys

57 %, 5-15

in neat (no solvent), in absence of solvent and catalyst; ratio of educts 1:1; at 55°C, for 6 h; contamination of the product by C2H5COC6H5 probably caused by the hydrolysis of the Sn product vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.2, page 97 - 113 ; (from Gmelin) View in Reaxys

38.2 %, 5-15

in neat (no solvent), in absence of solvent and catalyst; ratio of educts 4:3; at 55°C, for 20 h; contamination of the product by C2H5COC6H5 probably caused by hydrolysis of the Sn product Leusink; Noltes; Tetrahedron Letters; vol. 7; nb. 20; (1966); p. 2221 - 2225 ; (from Gmelin) View in Reaxys

38.2 %, 5-15

in neat (no solvent), in absence of solvent and catalyst; ratio of educts 4:3; at 55°C, for 20 h; contamination of the product by C2H5COC6H5 probably caused by hydrolysis of the Sn product vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.2, page 97 - 113 ; (from Gmelin) View in Reaxys

O (v4)

SnH

Sn O

Rx-ID: 26828007 View in Reaxys 659/824 Yield

Conditions & References heating for several hours; C2H5COC6H5 is formed in very small amt. only Leusink; Noltes; Tetrahedron Letters; vol. 7; nb. 20; (1966); p. 2221 - 2225 ; (from Gmelin) View in Reaxys heating for several hours; C2H5COC6H5 is formed in very small amt. only vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.2, page 97 - 113 ; (from Gmelin) View in Reaxys

Rx-ID: 26836197 View in Reaxys 660/824 Yield

Conditions & References hydrolysis Leusink; Noltes; Tetrahedron Letters; vol. 7; nb. 20; (1966); p. 2221 - 2225 ; (from Gmelin) View in Reaxys hydrolysis

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vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.2, page 97 - 113 ; (from Gmelin) View in Reaxys

(v4)

SnH

Sn Sn

Sn O

Rx-ID: 26836198 View in Reaxys 661/824 Yield

Conditions & References hydrogenolysis Leusink; Noltes; Tetrahedron Letters; vol. 7; nb. 20; (1966); p. 2221 - 2225 ; (from Gmelin) View in Reaxys hydrogenolysis vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.2, page 97 - 113 ; (from Gmelin) View in Reaxys HO

nickel-zinc oxide catalyst O

Rx-ID: 7446346 View in Reaxys 662/824 Yield

Conditions & References T= 250 °C , Hydrogenation Schuikin; Bel'skii; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 875; engl. Ausg. S. 859 View in Reaxys O HO

platinum/charcoal

Rx-ID: 7446347 View in Reaxys 663/824 Yield

Conditions & References T= 250 °C , Hydrogenation Schuikin; Bel'skii; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 875; engl. Ausg. S. 859 View in Reaxys HO

Raney nickel

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Rx-ID: 7449759 View in Reaxys 664/824 Yield

Conditions & References T= 250 °C , Hydrogenation Schuikin; Bel'skii; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 875; engl. Ausg. S. 859 View in Reaxys O

Rx-ID: 189824 View in Reaxys 665/824 Yield

Conditions & References With hydrogen, T= 450 °C , beim Leiten ueber einen Chrom-Mangan-Katalysator Jakowlew; Popa; Zhurnal Obshchei Khimii; vol. 28; (1958); p. 2475; engl. Ausg. S. 2510 View in Reaxys O O

Rx-ID: 757775 View in Reaxys 666/824 Yield

(v2)

Rx-ID: 310023 View in Reaxys 667/824 Yield

Conditions & References Tarbell; Price; Journal of Organic Chemistry; vol. 22; (1957); p. 245,248 View in Reaxys O

Rx-ID: 310024 View in Reaxys 668/824 Yield

Conditions & References With diethyl ether, diethylcadmium, toluene Tarbell; Price; Journal of Organic Chemistry; vol. 22; (1957); p. 245,248

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View in Reaxys O

O N

Rx-ID: 7446340 View in Reaxys 669/824 Yield

Conditions & References Grundy; Journal of the Chemical Society; (1957); p. 5087 View in Reaxys

O O

Cl H

Rx-ID: 588061 View in Reaxys 670/824 Yield

Conditions & References T= 230 - 260 °C , unter vermindertem Druck Bodendorf; Dettke; Chemische Berichte; vol. 89; (1956); p. 114 View in Reaxys O O

Rx-ID: 609454 View in Reaxys 671/824 Yield

Conditions & References With aluminum oxide, pyrographite, T= 425 °C Jakowlew; Kreimer; Zhurnal Obshchei Khimii; vol. 26; (1956); p. 3313; engl. Ausg. S. 3685 View in Reaxys O O

aluminium oxide Cl

Rx-ID: 6682935 View in Reaxys 672/824 Yield

Conditions & References T= 425 °C Jakowlew; Kreimer; Zhurnal Obshchei Khimii; vol. 26; (1956); p. 3313; engl. Ausg. S. 3685 View in Reaxys

aqueous propan-1-ol Cl

Cl O HO

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O HO

Rx-ID: 8258648 View in Reaxys 673/824 Yield

Conditions & References T= 65 °C , sowie bei 75grad und 80grad, Rate constant Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys OH

Rx-ID: 285460 View in Reaxys 674/824 Yield

Conditions & References Beim Erhitzen unter vermindertem Druck Marvel et al.; Journal of Organic Chemistry; vol. 20; (1955); p. 1785,1790 View in Reaxys O

O Na + O–

Rx-ID: 532619 View in Reaxys 675/824 Yield

Conditions & References With diethyl ether, ethylmagnesium bromide Grad; Wolkow; Zhurnal Obshchei Khimii; vol. 25; (1955); p. 1716; engl. Ausg. S. 1671 View in Reaxys O

3-dimethylamino-1-phenyl-propan-1-one hydrochloride

Rx-ID: 5931087 View in Reaxys 676/824 Yield

Conditions & References With ethanol, nickel, Hydrogenation Schultz; Bicking; Journal of the American Chemical Society; vol. 75; (1955); p. 1128 View in Reaxys O N

H N Br

Rx-ID: 22234 View in Reaxys 677/824 Yield

Conditions & References Lecomte; Dufour; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 234; (1952); p. 1887

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View in Reaxys O O

Rx-ID: 616101 View in Reaxys 678/824 Yield

Conditions & References With ethylaluminum dichloride, benzene Adkins; Scanley; Journal of the American Chemical Society; vol. 73; (1951); p. 2854 View in Reaxys O Cl

Cl S

Al Cl

Cl As

Cl Cl

Rx-ID: 7918929 View in Reaxys 679/824 Yield

Conditions & References Malinowskii; Zhurnal Obshchei Khimii; vol. 19; (1949); p. 130,132; Chem. Zentralbl.; 1950 I 2098 View in Reaxys O

Cl Cl S

As Al

Rx-ID: 7918930 View in Reaxys 680/824 Yield

Conditions & References Malinowskii; Zhurnal Obshchei Khimii; vol. 19; (1949); p. 130,132; Chem. Zentralbl.; 1950 I 2098 View in Reaxys O

Rx-ID: 357423 View in Reaxys 681/824 Yield

Conditions & References With water, sodium hydrogencarbonate Patent; Universal Oil Prod.; US2658919; (1948) View in Reaxys O

N Br–

+Mg

Rx-ID: 791863 View in Reaxys 682/824 Yield

Conditions & References With hydrogenchloride, diethyl ether, Kochen der wss. Phase des Reaktionsgemisches Hauser; Humphlett; Weiss; Journal of the American Chemical Society; vol. 70; (1948); p. 426

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View in Reaxys Shriner; Turner; Journal of the American Chemical Society; vol. 52; (1930); p. 1267 View in Reaxys With diethyl ether, Zers. des Reaktionsprodukts mit Wasser Bary; Bulletin des Societes Chimiques Belges; vol. 31; (1922); p. 408; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 124 View in Reaxys O H

Mg Br

Rx-ID: 597607 View in Reaxys 683/824 Yield

Conditions & References anschliessendes Behandeln mit wss. NaOBr-Loesung Palfray; Metayer; Panouse; Bulletin de la Societe Chimique de France; (1947); p. 766,770 View in Reaxys O Cl

Mg I

N O

Rx-ID: 728584 View in Reaxys 684/824 Yield

Conditions & References anschliessend Behandeln mit wss. Schwefelsaeure Panizzi; Gazzetta Chimica Italiana; vol. 77; (1947); p. 206,212 View in Reaxys O

3-oxo-2-methyl-3-phenyl-propionic acid isopropyl ester

Rx-ID: 5931088 View in Reaxys 685/824 Yield

Conditions & References With sulfuric acid, acetic acid Shivers; Dillon; Hauser; Journal of the American Chemical Society; vol. 69; (1947); p. 119,120 View in Reaxys O

3-oxo-2-methyl-3-phenyl-propionic acid tert-butyl ester

Rx-ID: 5931089 View in Reaxys 686/824 Yield

Conditions & References With sulfuric acid, acetic acid Shivers; Dillon; Hauser; Journal of the American Chemical Society; vol. 69; (1947); p. 119,120 View in Reaxys

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O O O

Na +

–

S O

Rx-ID: 8258637 View in Reaxys 687/824 Yield

Conditions & References und anschliessenden Destillieren im Hochvakuum bei 380-400grad Kratzl; Daeubner; Siegens; Monatshefte fuer Chemie; vol. 77; (1947); p. 146,155, 158 View in Reaxys O Cl (v2)

Rx-ID: 551162 View in Reaxys 688/824 Yield

Conditions & References With diethyl ether Gilman; Nelson; Recueil des Travaux Chimiques des Pays-Bas; vol. 55; (1936); p. 518,528, 529; Journal of the American Chemical Society; vol. 61; (1939); p. 741 View in Reaxys With benzene, T= 10 - 35 °C Cason; Journal of the American Chemical Society; vol. 68; (1946); p. 2078,2080 View in Reaxys O O (v2)

Rx-ID: 614977 View in Reaxys 689/824 Yield

Conditions & References With benzene, T= 5 - 14 °C , zuletzt bei 40-45grad Cason; Journal of the American Chemical Society; vol. 68; (1946); p. 2078,2080 View in Reaxys With diethyl ether, T= 0 °C Gilman; Nelson; Recueil des Travaux Chimiques des Pays-Bas; vol. 55; (1936); p. 518,528, 529; Journal of the American Chemical Society; vol. 61; (1939); p. 741 View in Reaxys O HO

aqueous NaOBr

Rx-ID: 7446342 View in Reaxys 690/824 Yield

Conditions & References Panouse; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 223; (1946); p. 745 View in Reaxys

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O O

Br–

+Mg

Rx-ID: 659976 View in Reaxys 691/824 Yield

Conditions & References T= -70 °C Newman; Booth; Journal of the American Chemical Society; vol. 67; (1945); p. 154 View in Reaxys O O

Cl Al

Rx-ID: 8258638 View in Reaxys 692/824 Yield

Conditions & References T= 40 °C , zuletzt bei 60grad und Behandlung des Reaktionsprodukts mit wss.HCl Sskoldinow; Kotscheschkow; Zhurnal Obshchei Khimii; vol. 12; (1942); p. 398; ; (1943); p. 3064 View in Reaxys O O

Cl Sn

Rx-ID: 26488779 View in Reaxys 693/824 Yield

Conditions & References 40°C in presence of AlCl3 Skoldinov, A. P.; Kocheshkov, K. A.; Zhurnal Obshchei Khimii; vol. 12; (1942); p. 398 - 401 View in Reaxys vol. Sn: Org.Verb.1; 1.1.1.2.4.7, page 73 - 76 ; (from Gmelin) View in Reaxys O

Rx-ID: 646264 View in Reaxys 694/824 Yield

Conditions & References With aluminium trichloride Malinowskii; Ljapina; Zhurnal Obshchei Khimii; vol. 11; (1941); p. 168; Chem. Zentralbl.; vol. 113; nb. II; (1942); p. 397 View in Reaxys O O

Rx-ID: 847657 View in Reaxys 695/824

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Yield

Conditions & References With aluminium trichloride Williams; Dickert; Krynitsky; Journal of the American Chemical Society; vol. 63; (1941); p. 2511 View in Reaxys O

HO Al

Rx-ID: 5931090 View in Reaxys 696/824 Yield

Conditions & References Malinowski; Ljapina; Zhurnal Obshchei Khimii; vol. 11; p. 169; ; (1941); p. 7384 View in Reaxys O

etheric diethyl cadmium-solution

Rx-ID: 5931096 View in Reaxys 697/824 Yield

Conditions & References With diethyl ether, T= 0 °C de Benneville; Journal of Organic Chemistry; vol. 6; (1941); p. 462,464 View in Reaxys O O

etheric diphenyl cadmium-solution O

Rx-ID: 5931097 View in Reaxys 698/824 Yield

Conditions & References T= 0 °C , anschliessendes Kochen de Benneville; Journal of Organic Chemistry; vol. 6; (1941); p. 462,464 View in Reaxys O

ethyl aluminium diiodide I

Rx-ID: 5931098 View in Reaxys 699/824 Yield

Conditions & References With benzene, weiteres Edukt: Diaethylaluminiumjodid Apperson; Iowa State College Journal of Science; vol. 16; (1941); p. 7 View in Reaxys

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O O

ethyl aluminium diiodide Cl

Rx-ID: 5931099 View in Reaxys 700/824 Yield

Conditions & References With benzene, weiteres Edukt: Diaethylaluminiumjodid Apperson; Iowa State College Journal of Science; vol. 16; (1941); p. 7 View in Reaxys O

ethyl aluminium diiodide Cl

diethyl aluminium iodide

Rx-ID: 5931100 View in Reaxys 701/824 Yield

Conditions & References Apperson; Iowa State College Journal of Science; vol. 16; (1941); p. 7 View in Reaxys

ethyl aluminium diiodide Cl

diethyl aluminium iodide

Rx-ID: 5931101 View in Reaxys 702/824 Yield

Conditions & References Apperson; Iowa State College Journal of Science; vol. 16; (1941); p. 7 View in Reaxys O

Rx-ID: 7061789 View in Reaxys 703/824 Yield

Conditions & References Williams; Dickert; Krynitsky; Journal of the American Chemical Society; vol. 63; (1941); p. 2511 View in Reaxys O

Rx-ID: 281524 View in Reaxys 704/824

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Yield

Conditions & References With ammonia, sodium, Behandlung des Reaktionsgemisches mit Aethylbromid und anschliessend Hydrolyse Kharasch; Sternfeld; Mayo; Journal of Organic Chemistry; vol. 5; (1940); p. 362,375 View in Reaxys O O

Na +

O–

Na +

–

Rx-ID: 5687997 View in Reaxys 705/824 Yield

Conditions & References nachfolgendes Behandeln mit Aethylbromid und Behandeln des Reaktionsprodukts mit Wasser Kharasch; Sternfeld; Mayo; Journal of Organic Chemistry; vol. 5; (1940); p. 362,375 View in Reaxys O H Br

H N

sodium

O O

Rx-ID: 5958128 View in Reaxys 706/824 Yield

Conditions & References Kharasch; Sternfeld; Mayo; Journal of Organic Chemistry; vol. 5; (1940); p. 362,375 View in Reaxys O H

Rx-ID: 14446 View in Reaxys 707/824 Yield

Conditions & References T= 0 °C Adamson; Kenner; Journal of the Chemical Society; (1939); p. 181,185 View in Reaxys O H

N N

Rx-ID: 14447 View in Reaxys 708/824 Yield

Conditions & References With diethyl ether, Schuetteln des Reaktionsprodukts mit wss. Schwefelsaeure Adamson; Kenner; Journal of the Chemical Society; (1939); p. 181,185 View in Reaxys

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O Al3+

HO 3

–

Rx-ID: 749874 View in Reaxys 709/824 Yield

Conditions & References T= 100 °C , auch unter Zusatz von Benzophenon oder anderen Ketonen Cox; Adkins; Journal of the American Chemical Society; vol. 61; (1939); p. 3364,3369 View in Reaxys O N HO Mg

2-hydroxy-2-phenyl-butyraldehyde-oxime

Rx-ID: 7446353 View in Reaxys 710/824 Yield

Conditions & References Freon; Annales de Chimie (Cachan, France); vol. <11>11; (1939); p. 474 View in Reaxys O

O S

aqueous NaOH

sulfenoacetic acid

Rx-ID: 7458105 View in Reaxys 711/824 Yield

Conditions & References Behaghel; Ratz; Chemische Berichte; vol. 72; (1939); p. 1257,1269 View in Reaxys

O –O

Na +

Rx-ID: 269555 View in Reaxys 712/824

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Yield

Conditions & References T= 180 °C Adickes; v. Muellenheim; Simson; Chemische Berichte; vol. 66; (1933); p. 1904,1907 View in Reaxys Magnani; McElvain; Journal of the American Chemical Society; vol. 60; (1938); p. 813,819 View in Reaxys H 2N

NH N

Mg+

Br–

Rx-ID: 492150 View in Reaxys 713/824 Yield

Conditions & References Biquard; Bulletin de la Societe Chimique de France; vol. <5>5; (1938); p. 209,211 View in Reaxys O

O H 2N

methanol. NH3 O

Rx-ID: 7061788 View in Reaxys 714/824 Yield

Conditions & References T= 130 - 140 °C Fuson et al.; Journal of the American Chemical Society; vol. 60; (1938); p. 1447,1450; Journal of Organic Chemistry; vol. 4; (1939); p. 111,117 View in Reaxys H 2N

NH N Mg

compound C45H75Cl3N12(?) O

Rx-ID: 8272876 View in Reaxys 715/824 Yield

Conditions & References Erwaermen des vom Aether befreiten Reaktionsgemisches in Benzol auf dem Dampfbad und anschliessend Behandeln mit Eis und NH4Cl

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Biquard; Bulletin de la Societe Chimique de France; vol. <5>5; (1938); p. 209,211 View in Reaxys O O

(v1)

Rx-ID: 609716 View in Reaxys 716/824 Yield

Conditions & References Gilman; Straley; Recueil des Travaux Chimiques des Pays-Bas; vol. 55; (1936); p. 821,823 View in Reaxys O H N

N Mg

NH 2

Rx-ID: 671156 View in Reaxys 717/824 Yield

Conditions & References Biquard; Bulletin de la Societe Chimique de France; vol. <5>3; (1936); p. 656,661,662,664 View in Reaxys O HO

H 2N

H 2N 2

O O

Rx-ID: 8258653 View in Reaxys 718/824 Yield

Conditions & References Herbst; Journal of the American Chemical Society; vol. 58; (1936); p. 2241 View in Reaxys

O H

H O

Ba(OH)2

O O

HO O

Rx-ID: 8258739 View in Reaxys 719/824 Yield

Conditions & References Lutz; Stuart; Journal of the American Chemical Society; vol. 58; (1936); p. 1885,1887, 1889; Journal of the American Chemical Society; vol. 61; (1939); p. 1465,1467, 1469 View in Reaxys

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Rx-ID: 7918928 View in Reaxys 720/824 Yield

Conditions & References Lauer; Spielman; Journal of the American Chemical Society; vol. 53; (1931); p. 1535 View in Reaxys Wright; Journal of the American Chemical Society; vol. 57; (1935); p. 1993,1998 View in Reaxys

H 2N

silver oxide

O HO O

O H

H 2N 2

Rx-ID: 8258654 View in Reaxys 721/824 Yield

Conditions & References Herbst; Clarke; Journal of Biological Chemistry; vol. 104; (1934); p. 770,776 View in Reaxys O

Rx-ID: 267477 View in Reaxys 722/824 Yield

Conditions & References T= 300 °C Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys

O O

Rx-ID: 267478 View in Reaxys 723/824 Yield

Conditions & References T= 300 °C Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys

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Rx-ID: 288223 View in Reaxys 724/824 Yield

Conditions & References T= 265 °C Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys O

O Se

Rx-ID: 6682932 View in Reaxys 725/824 Yield

Conditions & References Truchet; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 196; (1933); p. 1613 View in Reaxys O

2-methyl-1.4-diphenyl-butanedione-(1.4) O

Rx-ID: 7061787 View in Reaxys 726/824 Yield

Conditions & References T= 300 °C , im geschlossenen Gefaess Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys T= 223 °C , sowie bei 236grad, 250grad und 260grad, Kinetics MacDougall; Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4089,4094 View in Reaxys O

Rx-ID: 22126154 View in Reaxys 727/824 Yield

Conditions & References Reaction Steps: 2 1: KOH 2: 300 °C With potassium hydroxide Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys Reaction Steps: 2 1: KOH 2: 300 °C With potassium hydroxide

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Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys O

Br–

+Mg

Rx-ID: 791810 View in Reaxys 728/824 Yield

Conditions & References Thomson; Stevens; Journal of the Chemical Society; (1932); p. 2607,2610 View in Reaxys

NH 2

sodium nitrite

(+)-2-phenyl-propionaldehyde (?)

Rx-ID: 7918932 View in Reaxys 729/824 Yield

Conditions & References McKenzie; Luis; Mitchell; Chemische Berichte; vol. 65; (1932); p. 798,803 View in Reaxys O

Br–

+Mg

Rx-ID: 171327 View in Reaxys 730/824 Yield

Conditions & References Kohler, Erickson; Journal of the American Chemical Society; vol. 53; (1931); p. 2301,2307 View in Reaxys O HO

aqueous KOH

Rx-ID: 8258640 View in Reaxys 731/824

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Yield

Conditions & References Meisenheimer; Link; Justus Liebigs Annalen der Chemie; vol. 479; (1930); p. 211,248 View in Reaxys O

O HO O

O O

Rx-ID: 86777 View in Reaxys 732/824 Yield

Conditions & References With manganese(II) oxide, T= 460 °C Patent; Schering-Kahlbaum A.G.; DE555080; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 954 View in Reaxys O

<η-chloro-propyl>-benzene

Rx-ID: 5931091 View in Reaxys 733/824 Yield

Conditions & References With chromium(III) oxide, sulfuric acid, T= 68 °C Courtot; Pierron; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 1503 View in Reaxys O Cl

diluted Cr2O3-H2SO4

Rx-ID: 5931094 View in Reaxys 734/824 Yield

Conditions & References T= 68 °C , inactive form Courtot; Pierron; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 1503 View in Reaxys O

Rx-ID: 6682934 View in Reaxys 735/824 Yield

Conditions & References Rupe; Pieper; Helvetica Chimica Acta; vol. 12; (1929); p. 645 View in Reaxys

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H 2N

H Cl

sodium nitrite

Rx-ID: 8258645 View in Reaxys 736/824 Yield

Conditions & References Hartung; Munch; Journal of the American Chemical Society; vol. 51; (1929); p. 2266 View in Reaxys O

Rx-ID: 22296184 View in Reaxys 737/824 Yield

Conditions & References Reaction Steps: 2 1: nickel; aqueous alcohol / 68 - 73 °C / Hydrogenation 2: 150 °C / bei der Destillation mit ueberhitztem Wasserdampf With ethanol, nickel Rupe; Pieper; Helvetica Chimica Acta; vol. 12; (1929); p. 645 View in Reaxys

O O

chromic acid

Rx-ID: 7918931 View in Reaxys 738/824 Yield

Conditions & References Rising; Zee; Journal of the American Chemical Society; vol. 50; (1928); p. 1706; Journal of the American Chemical Society; vol. 49; (1927); p. 544 View in Reaxys

chromic acid

O H

Rx-ID: 8258651 View in Reaxys 739/824 Yield

Conditions & References liquid form Levy; Gallais; Bulletin de la Societe Chimique de France; vol. <4> 43; (1928); p. 865 View in Reaxys

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Mg+

Br– O

O HO

η.η-dibenzen-ethane HO

Rx-ID: 8263487 View in Reaxys 740/824 Yield

Conditions & References nebeneinander wechselnde Mengen;Produkt5:Aethan;Pr.6:1.3-Dioxy-2-methyl-1.3-diphenyl-propan;Pr.7:Benzylbenzoat Terentjew; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 159; (1927); p. 226; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 58; (1926); p. 1265,1268 View in Reaxys nebeneinander wechselnde Mengen; Produkt5:Aethan; Produkt6:1.3-Dioxy-2-methyl-1.3-diphenyl-propan Terentjew; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 159; (1927); p. 226; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 58; (1926); p. 1265,1268 View in Reaxys Meisenheimer; Justus Liebigs Annalen der Chemie; vol. 442; (1925); p. 200; Justus Liebigs Annalen der Chemie; vol. 446; (1926); p. 84 View in Reaxys Hess; Rheinboldt; Chemische Berichte; vol. 54; (1921); p. 2055 View in Reaxys O

N Mg Br

Rx-ID: 282261 View in Reaxys 741/824 Yield

Conditions & References With diethyl ether Maxim; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 1395; Annales de Chimie (Cachan, France); vol. <10> 9; (1928); p. 69,76 View in Reaxys With benzene Maxim; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 1395; Annales de Chimie (Cachan, France); vol. <10> 9; (1928); p. 69,76 View in Reaxys Maxim; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 1395; Annales de Chimie (Cachan, France); vol. <10> 9; (1928); p. 69,76 View in Reaxys

O HO O

Rx-ID: 292486 View in Reaxys 742/824 Yield

Conditions & References bei der Ozonspaltung

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Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys

O O

Rx-ID: 465091 View in Reaxys 743/824 Yield

Conditions & References bei der Ozonspaltung Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys O O

O S

alkali O

O O

η-methoxy-η-benzoyl-η-propylene O

Rx-ID: 5931112 View in Reaxys 744/824 Yield

Conditions & References Claisen; Chemische Berichte; vol. 59; (1926); p. 151 View in Reaxys v. Auwers; Chemische Berichte; vol. 45; (1912); p. 996; Justus Liebigs Annalen der Chemie; vol. 415; (1918); p. 227 View in Reaxys O

alkaline permanganate solution

Rx-ID: 7061785 View in Reaxys 745/824 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys O

oxygen

Rx-ID: 7061786 View in Reaxys 746/824 Yield

Conditions & References T= 78 °C Stephens; Journal of the American Chemical Society; vol. 48; (1926); p. 2921 View in Reaxys

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O O

KOH-solution HO

Rx-ID: 7918935 View in Reaxys 747/824 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys

OH HO

S OO

HO O

η-phenyl-η-valerolactone(?)

Rx-ID: 7918936 View in Reaxys 748/824 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys O

permanganate O

Rx-ID: 7918939 View in Reaxys 749/824 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys O

(v4)

Rx-ID: 8258639 View in Reaxys 750/824 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys

permanganate

Rx-ID: 8258644 View in Reaxys 751/824 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys

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KOH-solution

Îˇ-ethyl-trans-cinnamic acid

Rx-ID: 8258646 View in Reaxys 752/824 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys

O (v4)

Rx-ID: 8259093 View in Reaxys 753/824 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys O

O I

Rx-ID: 615120 View in Reaxys 754/824 Yield

Conditions & References With diethyl ether, sodium v. Bechi; Chemische Berichte; vol. 12; (1879); p. 463 View in Reaxys With diethyl ether, aluminium Leone; Gazzetta Chimica Italiana; vol. 55; (1925); p. 299,302; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5>33 II; (1924); p. 502,568 View in Reaxys O

ethyl aluminium diiodide

Rx-ID: 5931111 View in Reaxys 755/824 Yield

Conditions & References Leone; Gazzetta Chimica Italiana; vol. 55; (1925); p. 299,302; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5>33 II; (1924); p. 502,568

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View in Reaxys O O

Rx-ID: 646222 View in Reaxys 756/824 Yield

Conditions & References beim Leiten ueber ThO2, CdO, CaCO3, MnO oder Fe2O3 bei 400-500grad Sabatier; Murat; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 156; (1913); p. 1431; Annales de Chimie (Cachan, France); vol. <9> 4; (1915); p. 306 View in Reaxys Senderens; Annales de Chimie (Cachan, France); vol. <8> 28; (1913); p. 313 View in Reaxys Senderens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 150; (1910); p. 111,1336; Bulletin de la Societe Chimique de France; vol. <4> 7; (1910); p. 647 View in Reaxys Sabatier; Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 156; (1913); p. 1732; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 833 View in Reaxys Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 157; (1913); p. 221; Bulletin de la Societe Chimique de France; vol. <4> 15; (1914); p. 325 View in Reaxys With zirconium(VI) oxide Thierfelder; Daiber; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 130; (1923); p. 380,383, 384 View in Reaxys

N Br–

+Mg

O N

dipropionitrile

NH 2

Rx-ID: 6213321 View in Reaxys 757/824 Yield

Conditions & References Bary; Bulletin des Societes Chimiques Belges; vol. 31; (1922); p. 408; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 124 View in Reaxys O –O

O Cr 3+

Rx-ID: 454440 View in Reaxys 758/824 Yield

Conditions & References Apolit; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 172; (1921); p. 1494; Annales de Chimie (Cachan, France); vol. <10> 2; (1924); p. 98 View in Reaxys

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O O

chromium trioxide

Rx-ID: 7446343 View in Reaxys 759/824 Yield

Conditions & References Yeramian; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 173; (1921); p. 363 View in Reaxys O H

N H

Rx-ID: 6682939 View in Reaxys 760/824 Yield

Conditions & References Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 1354; Annales de Chimie (Cachan, France); vol. <9> 14; (1920); p. 341 View in Reaxys Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 156; (1913); p. 1806; Annales de Chimie (Cachan, France); vol. <9> 14; (1920); p. 339 View in Reaxys

diluted KOH-solution

N O

O H

N H

Rx-ID: 6682940 View in Reaxys 761/824 Yield

nickel HO

O HN

Rx-ID: 7446352 View in Reaxys 762/824 Yield

Conditions & References Hydrogenation Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 937

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View in Reaxys

O H 2N

Rx-ID: 7918934 View in Reaxys 763/824 Yield

Conditions & References Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 937 View in Reaxys

OH Cl

Rx-ID: 8258647 View in Reaxys 764/824 Yield

Conditions & References Hydrolysis Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 1354; Annales de Chimie (Cachan, France); vol. <9> 14; (1920); p. 341 View in Reaxys

HO Cl

Rx-ID: 8264148 View in Reaxys 765/824 Yield

NH4Cl

water

Rx-ID: 8282230 View in Reaxys 766/824 Yield

Conditions & References Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 169; (1919); p. 239 View in Reaxys Moureu; Mignonac; Annales de Chimie (Cachan, France); vol. <9> 14; (1920); p. 333; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 156; (1913); p. 1805 View in Reaxys Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 156; (1913); p. 1806; Annales de Chimie (Cachan, France); vol. <9> 14; (1920); p. 339 View in Reaxys

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O H Mg I

Rx-ID: 597286 View in Reaxys 767/824 Yield

Conditions & References Marshall; Journal of the Chemical Society; vol. 107; (1915); p. 521 View in Reaxys

O H

CrO3

KHSO4

Rx-ID: 8258641 View in Reaxys 768/824 Yield

Conditions & References Lepin; Reich; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 47; (1915); p. 153; Chem. Zentralbl.; vol. 87; nb. I; (1916); p. 787 View in Reaxys

O H

CrO3

KHSO4

Rx-ID: 8258642 View in Reaxys 769/824 Yield

Conditions & References Lepin; Reich; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 47; (1915); p. 153; Chem. Zentralbl.; vol. 87; nb. I; (1916); p. 787 View in Reaxys O

disodium derivative of η-phenyl-η.η-dibenzoyl-propane

Rx-ID: 5931095 View in Reaxys 770/824 Yield

Conditions & References Bauer; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 1682 View in Reaxys

Na + H –N

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Rx-ID: 6682938 View in Reaxys 771/824 Yield

Conditions & References nachf. Umsetzung mit Methyljodid Bauer; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 1682 View in Reaxys

O H

H N

N H

Rx-ID: 7918937 View in Reaxys 772/824 Yield

Conditions & References Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 1396; Annales de Chimie (Cachan, France); vol. <9>14; (1920); p. 349 View in Reaxys

O H H

H N

H O

Rx-ID: 7918938 View in Reaxys 773/824 Yield

OH HO

S OO

Rx-ID: 7446339 View in Reaxys 774/824 Yield

Conditions & References Straus; Berkow; Justus Liebigs Annalen der Chemie; vol. 401; (1913); p. 143 View in Reaxys O O O

O S

Rx-ID: 757042 View in Reaxys 775/824 Yield

Conditions & References With alkali

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v. Auwers; Chemische Berichte; vol. 45; (1912); p. 996; Justus Liebigs Annalen der Chemie; vol. 415; (1918); p. 227 View in Reaxys O O

Oâ&#x20AC;&#x201C;

Na +

Rx-ID: 782768 View in Reaxys 776/824 Yield

Conditions & References v. Auwers; Chemische Berichte; vol. 45; (1912); p. 997 View in Reaxys O O

Rx-ID: 782769 View in Reaxys 777/824 Yield

Conditions & References With sodium ethanolate v. Auwers; Chemische Berichte; vol. 45; (1912); p. 996; Justus Liebigs Annalen der Chemie; vol. 415; (1918); p. 227 View in Reaxys

O N

O O

zinc dust

O S

HS SH

Rx-ID: 5688002 View in Reaxys 778/824 Yield

Conditions & References unter Durchleiten von Wasserdampf Kelber; Schwarz; Chemische Berichte; vol. 45; (1912); p. 2487 View in Reaxys O

alcoholic KOH-solution

O O

Rx-ID: 7063379 View in Reaxys 779/824

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Yield

Conditions & References Abell; Journal of the Chemical Society; vol. 101; (1912); p. 1002 View in Reaxys

O O O

zinc

O S

Rx-ID: 5687999 View in Reaxys 780/824 Yield

Conditions & References Kelber; Schwarz; Chemische Berichte; vol. 44; (1911); p. 1698 View in Reaxys

O O

N O

zinc

O S

Rx-ID: 5688003 View in Reaxys 781/824 Yield

Conditions & References im Wasserdampf-Strom Kelber; Schwarz; Chemische Berichte; vol. 44; (1911); p. 1698 View in Reaxys O O

N-methyl-<l-ephedrine->-hydroxymethylate

Rx-ID: 5705015 View in Reaxys 782/824 Yield

Conditions & References η-methyl-η'-phenyl-ethylene oxide from l-ephedrine Schmidt,E.; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 309 View in Reaxys O

methylephedrinemethyl iodide

Rx-ID: 5931106 View in Reaxys 783/824 Yield

Conditions & References With silver(l) oxide, Destillation der entstandenen Base Schmidt,E.; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 309 View in Reaxys

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alcoholic NaOH-solution

O HO

Rx-ID: 8258649 View in Reaxys 784/824 Yield

Conditions & References Haller; Bauer; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 556; Annales de Chimie (Cachan, France); vol. <10> 1; (1924); p. 288 View in Reaxys

alcoholic NaOH-solution O

sodium salt of carbonic acid monoethyl ester

Rx-ID: 8287373 View in Reaxys 785/824 Yield

H H

OH H

Oâ&#x20AC;&#x201C;

methylphenylethylene oxide of boiling point 201-207 degree

Rx-ID: 8493001 View in Reaxys 786/824 Yield

Conditions & References beim Destillieren

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Schmidt,E.; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 309 View in Reaxys

O O

KMnO4 HO

Rx-ID: 8259797 View in Reaxys 787/824 Yield

Conditions & References η.η-diphenyl-η.η-heptadiene Reynolds; American Chemical Journal; vol. 44; (1910); p. 321 View in Reaxys

O O

Br Br O

Rx-ID: 370547 View in Reaxys 788/824 Yield

Conditions & References With ethanol, zinc Kohler; American Chemical Journal; vol. 42; (1909); p. 393 View in Reaxys O

hydrochloride of ephedrine

Rx-ID: 5931104 View in Reaxys 789/824 Yield

Conditions & References bei der Destillation Schmidt,E.; Archiv der Pharmazie (Weinheim, Germany); vol. 247; (1909); p. 148; Archiv der Pharmazie (Weinheim, Germany); vol. 252; (1914); p. 100 View in Reaxys O

hydrochloride of ephedrine

hydrochloride of pseudoephedrine

Rx-ID: 5931105 View in Reaxys 790/824 Yield

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O O

alcoholic potash

Rx-ID: 6163034 View in Reaxys 791/824 Yield

Conditions & References Kohler; American Chemical Journal; vol. 41; (1909); p. 425 View in Reaxys O

zinc Br

O O

Rx-ID: 7918933 View in Reaxys 792/824 Yield

Conditions & References Kohler; American Chemical Journal; vol. 42; (1909); p. 393 View in Reaxys O

Mg+ O

I– HO

Rx-ID: 65574 View in Reaxys 793/824 Yield

Conditions & References Wieland; Chemische Berichte; vol. 40; (1907); p. 1673; Chemische Berichte; vol. 42; (1909); p. 814 View in Reaxys O HO

alcoholic potash

Rx-ID: 7446341 View in Reaxys 794/824 Yield

Conditions & References Tiffeneau; Bulletin de la Societe Chimique de France; vol. <4> 1; (1907); p. 1212 View in Reaxys

O HO

CrO3 OH

Rx-ID: 7446344 View in Reaxys 795/824 Yield

Conditions & References Stern; Monatshefte fuer Chemie; vol. 26; (1905); p. 1559

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View in Reaxys O O OH HO

KMnO4

S OO

Rx-ID: 7447235 View in Reaxys 796/824 Yield

Conditions & References Klages; Heilmann; Chemische Berichte; vol. 37; (1904); p. 1452 View in Reaxys O

Rx-ID: 303083 View in Reaxys 797/824 Yield

Conditions & References durch Oxydation, 1-<11-etho-propen-(11)-yl>-benzene Klages; Chemische Berichte; vol. 36; (1903); p. 3692 View in Reaxys O H 2N

Mg Br

Rx-ID: 576818 View in Reaxys 798/824 Yield

Conditions & References Beis; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 576 View in Reaxys With diethyl ether, Zersetzung des Reaktionsprodukts mit Wasser Beis; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 576 View in Reaxys O

η-phenyl-η-amylene

Rx-ID: 5931085 View in Reaxys 799/824 Yield

Conditions & References Klages; Chemische Berichte; vol. 36; (1903); p. 3692 View in Reaxys

KMnO4

natrium carbonate

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Rx-ID: 8258652 View in Reaxys 800/824 Yield

Conditions & References η-ethyl-η-phenyl-itaconic acid Stobbe; Niedenzu; Justus Liebigs Annalen der Chemie; vol. 321; (1902); p. 101 View in Reaxys O O

Zn +

(v1)

I– Cl

Rx-ID: 614993 View in Reaxys 801/824 Yield

Conditions & References Michael; American Chemical Journal; vol. 25; (1901); p. 421; Chemische Berichte; vol. 34; (1901); p. 4036 View in Reaxys O O (v2)

Rx-ID: 615929 View in Reaxys 802/824 Yield

Conditions & References Michael; American Chemical Journal; vol. 25; (1901); p. 421; Chemische Berichte; vol. 34; (1901); p. 4036 View in Reaxys O

O (v2)

Rx-ID: 615930 View in Reaxys 803/824 Yield

Conditions & References With diethyl ether, Zersetzung des Reaktionsprodukts mit Eiswasser Michael; American Chemical Journal; vol. 25; (1901); p. 421; Chemische Berichte; vol. 34; (1901); p. 4036 View in Reaxys O

Mg I

N O

Rx-ID: 657786 View in Reaxys 804/824 Yield

Conditions & References Zersetzung mit Wasser Blaise; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 133; (1901); p. 1218 View in Reaxys

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Mg I

Rx-ID: 657787 View in Reaxys 805/824 Yield

Conditions & References With diethyl ether, Zersetzung des Reaktionsproduktes mit Wasser Blaise; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 133; (1901); p. 1218 View in Reaxys O

Mg+

I–

Rx-ID: 657969 View in Reaxys 806/824 Yield

Conditions & References Blaise; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 133; (1901); p. 1218 View in Reaxys

potassium hydroxide

Rx-ID: 6075586 View in Reaxys 807/824 Yield

Conditions & References T= 100 °C Nef; Justus Liebigs Annalen der Chemie; vol. 310; (1900); p. 323 View in Reaxys O O

aqueous KOH-solution

Rx-ID: 5687998 View in Reaxys 808/824 Yield

Conditions & References Ciamician; Silber; Chemische Berichte; vol. 27; (1894); p. 846; Gazzetta Chimica Italiana; vol. 24 I; (1894); p. 538 View in Reaxys O

11-nitro-1-propyl-benzene

Rx-ID: 5931086 View in Reaxys 809/824

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Yield

Conditions & References With hydrogenchloride, tin(ll) chloride Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 25; (1893); p. 530; Chem. Zentralbl.; vol. 65; nb. I; (1894); p. 465 View in Reaxys O

potassium salt of aci-11-nitro-1-propyl-benzene

Rx-ID: 5931107 View in Reaxys 810/824 Yield

Conditions & References With potassium nitrite, sulfuric acid Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 25; (1893); p. 530; Chem. Zentralbl.; vol. 65; nb. I; (1894); p. 465 View in Reaxys O

SnCl2

N O

Rx-ID: 7446345 View in Reaxys 811/824 Yield

Conditions & References Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 25; (1893); p. 530; Chem. Zentralbl.; vol. 65; nb. I; (1894); p. 465 View in Reaxys

–

O N

OH HO

K+

S OO

KNO2

Rx-ID: 8258643 View in Reaxys 812/824 Yield

Conditions & References Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 25; (1893); p. 530; Chem. Zentralbl.; vol. 65; nb. I; (1894); p. 465 View in Reaxys O

η-phenyl-allylene

Rx-ID: 5931084 View in Reaxys 813/824 Yield

Conditions & References With mercury dichloride, Erhitzen des Reaktionsprodukts mit Salzsaeure Koerner; Chemische Berichte; vol. 21; (1888); p. 276 View in Reaxys

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HgCl2

Rx-ID: 6682936 View in Reaxys 814/824 Yield

Conditions & References beim Erhitzen des Reaktionsprodukts mit Salzsaeure Koerner; Chemische Berichte; vol. 21; (1888); p. 276 View in Reaxys O

Cl Al

Rx-ID: 6682933 View in Reaxys 815/824 Yield

Conditions & References Pampel; Schmidt,G.; Chemische Berichte; vol. 19; (1886); p. 2897 View in Reaxys

O I I

red phosphorus

O O

Rx-ID: 5688000 View in Reaxys 816/824 Yield

Conditions & References T= 200 °C Morley; Green; Chemische Berichte; vol. 17; (1884); p. 3016 View in Reaxys

O OH HO

HO OH

S OO

Rx-ID: 5688001 View in Reaxys 817/824 Yield

Conditions & References Morley; Green; Chemische Berichte; vol. 17; (1884); p. 3016 View in Reaxys O

Rx-ID: 459421 View in Reaxys 818/824 Yield

Conditions & References With barium dihydroxide

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v. Pechmann; Chemische Berichte; vol. 15; (1882); p. 885 View in Reaxys O HO

aq. barium hydroxide solution O

Rx-ID: 8258650 View in Reaxys 819/824 Yield

Conditions & References v. Pechmann; Chemische Berichte; vol. 15; (1882); p. 885 View in Reaxys O

Rx-ID: 22359508 View in Reaxys 820/824 Yield

Conditions & References Reaction Steps: 2 1: aluminium chloride 2: aq. barium hydroxide solution With barium dihydroxide, aluminium trichloride v. Pechmann; Chemische Berichte; vol. 15; (1882); p. 885 View in Reaxys O

(v2)

O O

Zn(CN)2

benzcyanidin

Rx-ID: 6732159 View in Reaxys 821/824 Yield

Conditions & References Frankland; Louis; Journal of the Chemical Society; vol. 37; (1880); p. 745 View in Reaxys O O I

sodium

Rx-ID: 5931108 View in Reaxys 822/824

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Yield

Conditions & References v. Bechi; Chemische Berichte; vol. 12; (1879); p. 463 View in Reaxys O

Oâ&#x20AC;&#x201C; Ca 2+

calcium propionate

Rx-ID: 5931093 View in Reaxys 823/824 Yield

Conditions & References bei der Destillation Barry; Chemische Berichte; vol. 6; (1873); p. 1008 View in Reaxys O O (v2)

Zn O

Rx-ID: 609713 View in Reaxys 824/824 Yield

Conditions & References Kalle; Justus Liebigs Annalen der Chemie; vol. 119; (1861); p. 165 View in Reaxys Freund; Justus Liebigs Annalen der Chemie; vol. 118; (1861); p. 20 View in Reaxys

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