1-phenylpropan-2-one [Phenylacetone; P2P] [CAS 103-79-7; InChIKey QCCDLTOVEPVEJK-UHFFFAOYSA-N by Asch

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Rx-ID: 63801 View in Reaxys 1/502 Yield 85 %

Conditions & References With oxygen, sodium acetate, palladium dichloride in N,N-dimethyl acetamide, water, Time= 40h, T= 80 °C , p= 4560Torr , Wacker oxidation Mitsudome, Takato; Umetani, Takuya; Nosaka, Naoya; Mori, Kohsuke; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi; Angewandte Chemie - International Edition; vol. 45; nb. 3; (2006); p. 481 - 485 View in Reaxys

69 %

With oxygen, palladium diacetate, trifluoroacetic acid in water, dimethyl sulfoxide, Time= 8h, T= 70 °C , p= 760.051Torr , Sealed tube, Wacker Oxidation, regioselective reaction Wang, Yu-Fei; Gao, Ya-Ru; Mao, Shuai; Zhang, Yan-Lei; Guo, Dong-Dong; Yan, Zhao-Lei; Guo, Shi-Huan; Wang, Yong-Qiang; Organic Letters; vol. 16; nb. 6; (2014); p. 1610 - 1613 View in Reaxys With water, oxygen, palladium dichloride Smidt et al.; Angewandte Chemie; vol. 71; (1959); p. 176,180,182; Angewandte Chemie; vol. 74; (1962); p. 93 View in Reaxys Reaction Steps: 2 1: m-chloroperbenzoic acid 2: 92 percent / Co(CO)8 / methanol / 24 h / 40 °C With 3-chloro-benzenecarboperoxoic acid, Co(CO)8 in methanol Prandi; Namy; Menoret; Kagan; Journal of Organometallic Chemistry; vol. 285; nb. 1-3; (1985); p. 449 - 460 View in Reaxys Reaction Steps: 2 1: diethyl ether; yellow mercury (II)-oxide; iodine 2: diethyl ether; concentrated silver nitrate solution / weiteres Nebenprod.: Benzylaethylenglykol With diethyl ether, iodine, silver nitrate, mercury(II) oxide Porcher; Bulletin de la Societe Chimique de France; vol. <4> 31; (1922); p. 339 View in Reaxys Reaction Steps: 2 1: diethyl ether; yellow mercury (II)-oxide; iodine 2: silver nitrate; diethyl ether With diethyl ether, iodine, silver nitrate, mercury(II) oxide Porcher; Bulletin de la Societe Chimique de France; vol. <4> 31; (1922); p. 339 View in Reaxys With [PdCl2(tBu-BINC)], oxygen in N,N-dimethyl acetamide, water, Time= 48h, T= 70 °C , p= 760.051Torr , Wacker oxidation Naik, Anu; Meina, Liu; Zabel, Manfred; Reiser, Oliver; Chemistry - A European Journal; vol. 16; nb. 5; (2010); p. 1624 - 1628 View in Reaxys

56 %Chromat.

With tert.-butylhydroperoxide, carbon monoxide, palladium diacetate in methanol, acetonitrile, T= 50 °C , p= 760.051Torr Chen, Huoji; Cai, Congbi; Liu, Xiaohang; Li, Xianwei; Jiang, Huanfeng; Chemical Communications; vol. 47; nb. 44; (2011); p. 12224 - 12226 View in Reaxys

38 %Chromat.

With water, oxygen, palladium diacetate, butan-1-ol in N,N-dimethyl-formamide, Time= 24h, T= 100 °C , p= 760.051Torr , Schlenk technique

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Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Li, Chunsheng; Wu, Wanqing; Jiang, Huanfeng; Chemical Communications; vol. 51; nb. 46; (2015); p. 9575 - 9578 View in Reaxys

Rx-ID: 9685972 View in Reaxys 2/502 Yield 93 %

Conditions & References Stage 1: With NH4I, water, sodium lauryl sulfate, Time= 0.5h Stage 2: With Oxonereg;, Time= 1.16h, T= 20 °C , regioselective reaction Swamy, Peraka; Reddy, Marri Mahender; Naresh, Mameda; Kumar, Macharla Arun; Srujana, Kodumuri; Durgaiah, Chevella; Narender, Nama; Advanced Synthesis and Catalysis; vol. 357; nb. 6; (2015); p. 1125 - 1130 View in Reaxys

84 %

With [hydroxy(tosyloxy)iodo]benzene in methanol, Time= 0.333333h, T= 20 °C Justik, Michael W.; Koser, Gerald F.; Tetrahedron Letters; vol. 45; nb. 32; (2004); p. 6159 - 6163 View in Reaxys

81 %

1-Phenylpropan-2-one (17). General procedure: The reaction was performed following the General Procedure B, but using PhI (0.204 g, 0.114 mL, 1.00 mmol), mCPBA (77percent, 0.224 g, 1.00 mmol), and TsOH.H2O (0.19 g, 1.0 mmol) in HFIP/CH2Cl2 (1:6, 5 mL). After 30 min, H2O (0.40 mL, 22 mmol) and alkene 16 (0.094 g, 0.80 mmol) was added at 0 oC. Purification by flash column chromatography (5-8percent EtOAc in hexane) gave compound 175 (0.087 g, 0.65 mmol, 81percent) as colorless oil. With iodobenzene, toluene-4-sulfonic acid, m-chloroperbenzoic acid in dichloromethane, water, T= 0 °C Ahmad, Anees; Scarassati, Paulo; Jalalian, Nazli; Olofsson, Berit; Silva Jr., Luiz F.; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5818 - 5820 View in Reaxys

81 %

catalytic oxidative 1,2-shift ofarylalkenes General procedure: To a mixture solvent MeCN-H2O (5:1) (2 mL), α-methylstyrene (0.5 mmol), Oxone ® (1.0 mmol) and NaI (0.05 mmol) were added. The mixture was stirred at room temperature for 15 h, then H2O (5 mL) was added. Extraction of the mixture with CH2Cl2 (3 * 5 mL) and the combined organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel plate (5:1 hexane-ethyl acetate) to give 1-phenylpropan-2-one in 81percent of yield. With Oxonereg;, sodium iodide in water, acetonitrile, Time= 15h, T= 20 °C , Green chemistry, Reagent/catalyst, Solvent, Time Zhu, Min; Zhao, Yang; Chinese Chemical Letters; vol. 26; nb. 2; (2015); p. 248 - 250 View in Reaxys

76 %

With Oxonereg;, iodine in DME, water, Time= 3h, T= 20 °C , regioselective reaction Kodumuri, Srujana; Peraka, Swamy; Mameda, Naresh; Chevella, Durgaiah; Banothu, Rammurthy; Nama, Narender; RSC Advances; vol. 6; nb. 8; (2016); p. 6719 - 6723 View in Reaxys

64 %

Stage 1: With 2-Iodo-5-methylbenzenesulfonic acid in tert-butyl methyl ether, water, isopropyl alcohol, Time= 0.0833333h, T= 22 °C , Inert atmosphere Stage 2: With Oxonereg; in tert-butyl methyl ether, water, isopropyl alcohol, Time= 22h, T= 22 °C , Inert atmosphere, Further stages Purohit, Vikram C.; Allwein, Shawn P.; Bakale, Roger P.; Organic Letters; vol. 15; nb. 7; (2013); p. 1650 - 1653 View in Reaxys

59 %

With 1,3-dihydroxy-1H-1λ3-benzo[d][1,2]iodoxol-1-yl trifluoromethanesulfonate in dichloromethane, water, Time= 24h, T= 20 °C

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Yoshimura, Akira; Nguyen, Khiem C.; Klasen, Scott C.; Saito, Akio; Nemykin, Victor N.; Zhdankin, Viktor V.; Chemical Communications; vol. 51; nb. 37; (2015); p. 7835 - 7838 View in Reaxys Reaction Steps: 2 1: C6H5IO/CH3OH / FSO3H / 0.25 h 2: 81 percent With methanol, iodosylbenzene, fluorosulphonic acid Moriarty, Robert M.; Khosrowshahi, Jaffar S.; Prakash, Om; Tetrahedron Letters; vol. 26; nb. 25; (1985); p. 2961 - 2964 View in Reaxys Reaction Steps: 2 1: 80 percent / I2, lithium perchlorate, 2,6-lutidine / Ambient temperature; electrochemical oxidation 2: aq. hydrochloric acid With 2,6-dimethylpyridine, hydrochlorid acid, iodine, lithium perchlorate Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu; Ikeda, Kaoru; Fujita, Tetsuhiro; Kamada, Tohru; Tetrahedron Letters; vol. 30; nb. 39; (1989); p. 5309 - 5312 View in Reaxys Reaction Steps: 2 1: lithium perchlorate / direct anodic oxidation 2: aq. hydrochloric acid With hydrochlorid acid, lithium perchlorate Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu; Ikeda, Kaoru; Fujita, Tetsuhiro; Kamada, Tohru; Tetrahedron Letters; vol. 30; nb. 39; (1989); p. 5309 - 5312 View in Reaxys With sodium hydrogen sulphate monohydrate, (diacetoxyiodo)benzene in water, T= 20 °C Yusubov, Mehman S.; Yusubova, Rosa Y.; Funk, Tatyana V.; Chi, Ki-Whan; Zhdankin, Viktor V.; Synthesis; nb. 15; (2009); p. 2505 - 2508; Art.No: M01009SS View in Reaxys

Rx-ID: 9178539 View in Reaxys 3/502 Yield 98 %

Conditions & References Stage 1: With aniline, [(η5-cyclopentadienyl)2Ti(η2-Me3SiC2SiMe3)] in toluene, Time= 24h, T= 140 °C Stage 2: With hydrogenchloride Tillack, Annegret; Garcia Castro, Ivette; Hartung, Christian G.; Beller, Matthias; Angewandte Chemie - International Edition; vol. 41; nb. 14; (2002); p. 2541 - 2543 View in Reaxys Stage 1: With (S)-1-phenyl-ethylamine, Ind2TiMe2 in toluene, Time= 48h, T= 105 °C Stage 2: With silica gel in toluene, Time= 12h, T= 25 °C Pohlki, Frauke; Bytschkov, Igor; Siebeneicher, Holger; Heutling, Andreas; Koenig, Wilfried A.; Doye, Sven; European Journal of Organic Chemistry; nb. 9; (2004); p. 1967 - 1972 View in Reaxys Reaction Steps: 2 1: bis(2,6-di-tert-butyl-4-methylphenoxo)bis(dimethylamido)Ti / toluene / 48 h / 130 °C 2: aq. HCl With hydrogenchloride, {Ti(2,6-(CMe3)2C6H3O)2(NMe2)2} in toluene Khedkar, Vivek; Tillack, Annegret; Beller, Matthias; Organic Letters; vol. 5; nb. 25; (2003); p. 4767 - 4770 View in Reaxys

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Reaction Steps: 2 1: [Cp2Ti(η2-Me3SiCCSiMe3)] / toluene / 24 h / 100 °C 2: 5 percent HCl With hydrogenchloride, [(η5-cyclopentadienyl)2Ti(η2-Me3SiC2SiMe3)] in toluene Tillack, Annegret; Garcia Castro, Ivette; Hartung, Christian G.; Beller, Matthias; Angewandte Chemie - International Edition; vol. 41; nb. 14; (2002); p. 2541 - 2543 View in Reaxys

Rx-ID: 8868700 View in Reaxys 4/502 Yield

Conditions & References

46 %, 45 % With tetrafluoroboric acid, oxygen, palladium diacetate, p-benozquinone 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 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-β-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: δ 200.8, 136.9, 132.9, 128.5, 128.0, 31.8, 8.2. B: 1H NMR: δ 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: δ 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-benozquinone 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

Rx-ID: 1983191 View in Reaxys 5/502 Yield 99 %

Conditions & References With periodic acid, PFC in acetonitrile, Time= 2h, T= 0 °C Hunsen, Mo; Journal of Fluorine Chemistry; vol. 126; nb. 9-10; (2005); p. 1356 - 1360

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View in Reaxys 99 %

With sodium hydrogencarbonate, sodium bromide 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

98 %

With chromium(VI) oxide, periodic acid in water, acetonitrile, T= 0 °C Zhao, Mangzhu; Li, Jing; Song, Zhiguo; Desmond, Richard; Tschaen, David M.; Grabowski, Edward J. J.; Reider, Paul J.; Tetrahedron Letters; vol. 39; nb. 30; (1998); p. 5323 - 5326 View in Reaxys

98 %

With periodic acid, pyridinium chlorochromate in acetonitrile, Time= 2h, T= 0 - 20 °C Hunsen, Mo; Tetrahedron Letters; vol. 46; nb. 10; (2005); p. 1651 - 1653 View in Reaxys

98 %

With hydrogen peroxide in water, Time= 0.5h, T= 80 - 120 °C , Microwave irradiation, Green chemistry, Time, Temperature Rajabi, Fatemeh; Pineda, Antonio; Naserian, Sareh; Balu, Alina Mariana; Luque, Rafael; Romero, Antonio A.; Green Chemistry; vol. 15; nb. 5; (2013); p. 1232 - 1237 View in Reaxys

95 %

With benzyltriphenylphosphonium peroxodisulfate in acetonitrile, Time= 0.6h, Heating, Oxidation Mohammadpoor-Baltork, Iraj; Hajipour, Abdol Reza; Mohammadi, Hasan; Bulletin of the Chemical Society of Japan; vol. 71; nb. 7; (1998); p. 1649 - 1653 View in Reaxys

95 %

With trinitratocerium(IV) bromate, Time= 0.8h, Heating Shirini, Farhad; Esm-Hosseini, Majid; Hejazi, Zoha; Synthetic Communications; vol. 35; nb. 22; (2005); p. 2913 2919 View in Reaxys

95 %

With N-methyl-1H-imidazole, [Cu(MeCN)]4*CF3SO3, 4,4'-Dimethoxy-2,2'-bipyridin, ABNO, oxygen in acetonitrile, Time= 1h, T= 20 °C Steves, Janelle E.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 135; nb. 42; (2013); p. 15742 - 15745 View in Reaxys

94 %

With periodic acid, .LAMBDA.-(+)-tris(acetylacetonato)chromium(III) in acetonitrile, Time= 1h, T= 20 °C Xu, Liang; Trudell, Mark L.; Tetrahedron Letters; vol. 44; nb. 12; (2003); p. 2553 - 2555 View in Reaxys

93 %

With ammonium dichromate(VI), silica gel, zirconium tetrachloride in hexane, Time= 1.7h, Heating Shirini, Farhad; Ali Zolfigol, Mohammad; Pourhabib, Akram; Journal of Chemical Research - Part S; nb. 11; (2001); p. 476 - 477 View in Reaxys

93 %

With prolinium chlorochromate in hexane, Time= 3h, Heating Mamaghani; Shirini; Parsa; Russian Journal of Organic Chemistry; vol. 38; nb. 8; (2002); p. 1113 - 1115 View in Reaxys

93 %

With PhIO2, bromine, sodium nitrite in water, Time= 1h, T= 55 °C Mu, Ruizhu; Liu, Zhongquan; Yang, Zhanjun; Liu, Zhengang; Wu, Longmin; Liu, Zhong-Li; Advanced Synthesis and Catalysis; vol. 347; nb. 10; (2005); p. 1333 - 1336 View in Reaxys

93 %

With hydrogen peroxide, poly(N-i-propylacrylamide)-phototungstic acid-based catalyst in water, Time= 6h, T= 90 °C

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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 91 %

With silica gel supported bis(trimethylsilyl) chromate in dichloromethane, Time= 0.5h, T= 40 °C Lee, Jong Gun; Lee, Jung A.; Sohn, Soo Yun; Synthetic Communications; vol. 26; nb. 3; (1996); p. 543 - 549 View in Reaxys

90 %

With ammonium dichromate(VI), Mg(HSO4)2, silica gel, Time= 0.166667h, T= 20 °C Shirini; Zolfigol; Mallakpour; Hajipour; Australian Journal of Chemistry; vol. 54; nb. 6; (2001); p. 405 - 406 View in Reaxys

90 %

With KBrO3, tetrachlorosilane, silica gel in hexane, Time= 1.16667h, Heating Shirini, Farhad; Zolfigol, Mohammad Ali; Khaleghi, Mahroo; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 178; nb. 10; (2003); p. 2107 - 2110 View in Reaxys

90 %

With tris[trinitratocerium(IV)] paraperiodate, Time= 0.33h, T= 90 °C Shirini; Esm-Hosseini; Hejazi; Mohammadpoor-Baltork; Journal of Chemical Research; nb. 1; (2006); p. 29 - 31 View in Reaxys

90 %

With iron nitrate (III), BaCl2, Time= 0.416667h, T= 90 °C Habibi, Davood; Zolfigol, Mohammad Ali; Shirini, Farhad; Safaiee, Maliheh; Abedini, Masumeh; Rahmani, Payam; South African Journal of Chemistry; vol. 60; (2007); p. 17 - 19 View in Reaxys

88 %

With periodic acid, pyridinium chlorochromate in acetonitrile, Time= 1h, T= 0 °C Romanov-Michailidis, Fedor; Sedillo, Kassandra F.; Neely, Jamie M.; Rovis, Tomislav; Journal of the American Chemical Society; vol. 137; nb. 28; (2015); p. 8892 - 8895 View in Reaxys

86 %

With ammonium dichromate(VI), aluminum(III) hydrogen sulfate, silica gel, Time= 1.2h, T= 20 °C Shirini, Farhad; Zolfigol, Mohammad A.; Abedini, Masoumeh; Salehi, Peyman; Mendeleev Communications; vol. 13; nb. 6; (2003); p. 265 - 267 View in Reaxys

85 %

With pyridine, trichloroisocyanuric acid in acetone, Time= 0.333333h Hiegel; Nalbandy; Synthetic Communications; vol. 22; nb. 11; (1992); p. 1589 - 1595 View in Reaxys

85 %

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= 3h, 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

84 %

32.A : A. l-phenylpropan-2-one A. l-phenylpropan-2-one [00367] A solution of l-phenylpropan-2-ol (2.72 g, 20 mmol) in CH2CI2 (20 mL) was added pyridinium chlorochromate (PCC, 5.4 g, 25 mmol) at 0 °C and the mixture was stirred for 3 h. The mixture was concentrated and purified by flash column chromatography (PE/EtOAc = 20: 1) to give the title compound (2.3 g, 84percent) as a yellow oil. With pyridinium chlorochromate in dichloromethane, Time= 3h, T= 0 °C Patent; QUANTICEL PHARMACEUTICALS, INC; NIE, Zhe; STAFFORD, Jeffrey, Alan; VEAL, James, Marvin; WALLACE, Michael, Brennan; WO2014/89364; (2014); (A1) English View in Reaxys

7/149

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83 %

With pyridine, tri-n-butyl phosphine oxide, oxygen, palladium diacetate in toluene, Time= 24h, T= 80 °C , p= 750.075Torr , Molecular sieve Gowrisankar, Saravanan; Neumann, Helfried; Goerdes, Dirk; Thurow, Kerstin; Jiao, Haijun; Beller, Matthias; Chemistry - A European Journal; vol. 19; nb. 47; (2013); p. 15979 - 15984 View in Reaxys

80 %

With sodium carbonate, acetone, BQC, di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium in water, Time= 17h, 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

77 %

Stage 1: With oxalyl dichloride, dimethyl sulfoxide in dichloromethane, T= -78 °C , Inert atmosphere, Swern oxidation Stage 2: With triethylamine in dichloromethane, T= 20 °C , Cooling, Inert atmosphere, Swern oxidation Ema, Tadashi; Ura, Norichika; Yoshii, Masataka; Korenaga, Toshinobu; Sakai, Takashi; Tetrahedron; vol. 65; nb. 46; (2009); p. 9583 - 9591 View in Reaxys

75 %

With potassium bromide in water, acetonitrile, Time= 12h, T= 20 °C Chen, Jiang-Min; Zeng, Xiao-Mei; Zhdankin, Viktor V.; Synlett; nb. 18; (2010); p. 2771 - 2774 View in Reaxys

70 %

With KBrO3, zirconium(IV) oxychloride in acetonitrile, Time= 0.5h, Heating Shirini, Farhad; Zolfigol, Mohammad Ali; Mollarazi, Esmail; Synthetic Communications; vol. 35; nb. 11; (2005); p. 1541 - 1545 View in Reaxys

70 %

With Dess-Martin periodinane in dichloromethane, Time= 2h, T= 0 - 20 °C , Inert atmosphere Denton, Justin R.; Davies, Huw M. L.; Organic Letters; vol. 11; nb. 4; (2009); p. 787 - 790 View in Reaxys

50 %

With tert -butyl hydrogen peroxide, tris(triphenylphosphine)ruthenium(II) chloride in benzene, Time= 20h, Ambient temperature Murahashi; Naota; Synthesis; nb. 4; (1993); p. 433 - 440 View in Reaxys

50 %

With tert -butyl hydrogen peroxide, tris(triphenylphosphine)ruthenium(II) chloride, Time= 20h Murahashi; Naota; Russian Journal of Organic Chemistry; vol. 32; nb. 2; (1996); p. 203 - 213 View in Reaxys

40 %

With [Pd(N,N'-bis(2,6-(diisopropyl)phenyl)imidazol-2-ylidene)(PCy3)], oxygen, acetic acid in toluene, Time= 14.5h, 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

14 %

With tert -butyl hydrogen peroxide, Rh+(diphos) in methanol, Time= 24h, T= 70 °C , several conditions investigated and other solvent also investigated, Product distribution Mueller, Paul; Idmoumaz, Hamid; Journal of Organometallic Chemistry; vol. 345; (1988); p. 187 - 200 View in Reaxys With oxalyl dichloride, dimethyl sulfoxide, triethylamine, 1.) dichloromethane, -70 deg C, 15 min; 2.) r.t., 15 min, Multistep reaction Takano, Seiichi; Inomata, Kohei; Samizu, Kiyohiro; Tomita, Shun'ichi; Yanase, Masashi; et al.; Chemistry Letters; (1989); p. 1283 - 1284 View in Reaxys

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85 % Spectr.

With dimethyldioxiran 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

66 % Chro- With Mukayama reagent, zinc oxide in dichloromethane, Time= 0.5h, T= 20 °C mat. Matsuo, Jun-Ichi; Kitagawa, Hideo; Iida, Daisuke; Mukaiyama, Teruaki; Chemistry Letters; nb. 2; (2001); p. 150 151 View in Reaxys With dimethyldioxiran in acetone, T= 0 °C , Kinetics Angelis, Yiannis S.; Hatzakis, Nikos S.; Smonou, Ioulia; Orfanopoulos, Michael; Tetrahedron Letters; vol. 42; nb. 22; (2001); p. 3753 - 3756 View in Reaxys 66 % Chro- With Mukayama reagent, zinc oxide in dichloromethane, Time= 0.5h, T= 20 °C mat. Matsuo, Jun-Ichi; Iida, Daisuke; Tatani, Kazuya; Mukaiyama, Teruaki; Bulletin of the Chemical Society of Japan; vol. 75; nb. 2; (2002); p. 223 - 234 View in Reaxys With tert -butyl hydrogen peroxide, tetrabutyl-ammonium chloride, BQC, 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 Reaction Steps: 2 1: 91 percent / CAN; 1-n-butylpyridinium chloroferrate / 0.5 h / 20 °C 2: 92 percent / 1-n-butylpyridinium chloroferrate; pyridinium chlorochromate / 0.58 h / 50 °C With ammonium cerium(IV) nitrate, 1-n-butylpyridinium tetrachloroferrate, pyridinium chlorochromate Khosropour, Ahmad R.; Khodaei, Mohammad M.; Ghaderi, Sattar; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 3; (2006); p. 326 - 330 View in Reaxys Reaction Steps: 2 1: 91 percent / CAN; 1-n-butylpyridinium chloroferrate / 0.5 h / 20 °C 2: 87 percent / 1-n-butylpyridinium chloroferrate; pyridinium chlorochromate / 0.47 h / 50 °C With ammonium cerium(IV) nitrate, 1-n-butylpyridinium tetrachloroferrate, pyridinium chlorochromate Khosropour, Ahmad R.; Khodaei, Mohammad M.; Ghaderi, Sattar; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 3; (2006); p. 326 - 330 View in Reaxys 6 %Chromat.

With μ-oxo-(tetra-tert-butylphthalocyaninato)iron(III), iodosylbenzene in dichloromethane, Time= 3.5h, T= 20 °C Geraskin, Ivan M.; Luedtke, Matthew W.; Neu, Heather M.; Nemykin, Victor N.; Zhdankin, Viktor V.; Tetrahedron Letters; vol. 49; nb. 52; (2008); p. 7410 - 7412 View in Reaxys 5.A :1-Phenyl-2-propanol (10 mL, 71 mmol) was dissolved in acetone (800 mL), cooled to 10° C. and Jones reagent was added slowly until an orange color persisted. After 5 min, 2-propanol was added to destroy the excess chromium reagent. The reaction mixture was diluted with Et2O (500 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted once more with Et2O (200 mL). The ether extracts were combined and washed with brine (2*100 mL), dried over MgSO4 and evaporated under reduced pressure. The product was obtained as a yellow oil that was used directly in the next step. Stage 1: With Jone's reagent in acetone, Time= 0.0833333h, T= 10 °C Stage 2: With isopropyl alcohol in acetone

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Patent; Andersen, Denise Lyn; Chang, Catherine H.; Falsey, James R.; Frohn, Michael J.; Hong, Fang-Tsao; Liao, Hongyu; Liu, Longbin; Lopez, Patricia; Retz, Daniel Martin; Rishton, Gilbert M.; Rzasa, Robert M.; Siegmund, Aaron; Tadesse, Seifu; Tamayo, Nuria; Tegley, Christopher M.; US2006/69110; (2006); (A1) English View in Reaxys Typical procedure of oxidation of alcohols with PS-DCIB 2 in CH3CN-H2O: To a solution of benzyl alcohol 13a (0.021 g, 0.2 mmol) and pyridine (0.052 mL, 0.6mmol) in CH3CN-H2O (2 mL, v/v =1:1) was added PS-DICB 2 (0.223 g, 0.3 mmol) and TEMPO (0.003 g, 0.02 mmol) at room temperature, and the mixture was warmed up to 50 °C and magnetically stirred until the alcohol was consumed (monitored by TLC). The mixture was filtered, and the PS-IB resin was washed with CH3CN (3 x 1 mL) and collected for reuse. To the filtrate was added 2 mL of a standard solution of 2,4-dinitrophenylhydrazine (prepared from 3 g 2,4-DNP, 15 mL concd H2SO4, 70 mL EtOH,and 20 mL H2O). The precipitate was filtered, washed with water and 95percent ethanol, dried in vacuum to give 2,4-dinitrophenyl-hydrazone 14a (0.053 g, 92percent) With pyridine, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in water, acetonitrile, Time= 3.5h, T= 50 °C Chen, Jiang-Min; Zeng, Xiao-Mei; Middleton, Kyle; Zhdankin, Viktor V.; Tetrahedron Letters; vol. 52; nb. 16; (2011); p. 1952 - 1955 View in Reaxys 1 :Preparation of l-phenylpropan-2-one (3B): A stock solution of periodic acid/chromium trioxide was prepared according to WO 99/52850 by dissolving periodic acid (11.4 g, 50.0 mmol) and chromium trioxide (23 mg, 1.2 mol percent) in wet acetonitrile (0.75percent H20) to a volume of 114 mL. This stock solution (104.5 mL) was added to a solution of lphenylpropan-2-ol (3A) (5.0 g, 36.71 mmol) in wet acetonitrile (150 mL, 0.75percent H20) at 0 °C over 1 h, maintaining internal temperature below 5 °C. The reaction was quenched with K2HP04 (11.5 g, 50.5 mmol) in H20 (60 mL).Dichloromethane was added and organic layer separated and washed with brine/H20 (2 x 100 mL), followed by saturated NaHS03/brine. The organic layer was dried(MgS04), filtered and concentrated to give 3B as a yellow oil (5.1 g). 'HNMR: 300 MHz, (CDC13) δ 7.35-7.10 (m, 5H), 3.65 (s, 2H), 2.11 (s, 3 H). With chromium(VI) oxide, periodic acid in water, acetonitrile, Time= 1h, T= 0 - 5 °C Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BJORNSON, Kyla; GUO, Hongyan; HALCOMB, Randall, L.; LINK, John, O.; MCFADDEN, Ryan; MITCHELL, Michael, L.; ROETHLE, Paul; TRENKLE, James, D.; VIVIAN, Randall, W.; XU, Lianhong; WO2012/3497; (2012); (A1) English View in Reaxys 82 %Spectr.

With oxygen in 1,4-dioxane, Time= 22h, T= 80 °C Asao, Naoki; Hatakeyama, Naoya; Menggenbateer; Minato, Taketoshi; Ito, Eisuke; Hara, Masahiko; Kim, Yousoo; Yamamoto, Yoshinori; Chen, Mingwei; Zhang, Wei; Inoue, Akihisa; Chemical Communications; vol. 48; nb. 38; (2012); p. 4540 - 4542 View in Reaxys

94 %Spectr.

With C10H16NO5, potassium carbonate, bis(trifluoroacetato)-phenyliodine, Time= 0.75h, T= 20 °C , Catalytic behavior, Reagent/catalyst Hamada, Shohei; Furuta, Takumi; Wada, Yoshiyuki; Kawabata, Takeo; Angewandte Chemie - International Edition; vol. 52; nb. 31; (2013); p. 8093 - 8097; Angew. Chem.; vol. 125; nb. 31; (2013); p. 8251 - 8255,5 View in Reaxys

102 mg

4.1 : Production Example 4 Synthesis of Compound 9 (1) 1-Phenyl-2 -propanol (h) (428 mg) was dissolved in dichloromethane (16 mL) , subsequently molecular sieves 4A (400 mg) , N-methylmorpholine (1.10 g) andtetrapropylammonium perruthenate (110 mg) were added thereto and the solution was stirred for 24 hours at room temperature under nitrogen atmosphere. The reaction solution was filtered using a silica gel short column, and the filtrate was dried under reduced pressure and subsequently purified by silica gel chromatography, thereby obtaining ketone (i) (102 mg) . With O(CH2CH2)2NCH3, tetrapropylammonium perruthennate in dichloromethane, Time= 24h, T= 20 °C , Molecular sieve, Inert atmosphere Patent; KAO CORPORATION; KINOSHITA, Kazuki; SHIRAI, Tomohiro; KUMIHASHI, Kentaro; FUJIHARA, Hirohisa; MUGITA, Nanae; WO2013/103155; (2013); (A1) English View in Reaxys

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With dimethyl sulfoxide, N,N- diisopropylethylamine, trifluoroacetic anhydride in dichloromethane, T= -20 °C , Flow reactor Van Der Linden, Jacobus J. M.; Hilberink, Peter W.; Kronenburg, Claudia M. P.; Kemperman, Gerardus J.; Organic Process Research and Development; vol. 12; nb. 5; (2008); p. 911 - 920 View in Reaxys Reaction Steps: 2 1: Candida antarctica lipase B / toluene / 20 °C / |Enzymatic reaction 2: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / |Enzymatic reaction With Candida antarctica lipase B, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in toluene Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys Reaction Steps: 3 1: Candida antarctica lipase B / toluene / 20 °C / |Enzymatic reaction 2: potassium hydroxide; water / methanol 3: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / |Enzymatic reaction With Candida antarctica lipase B, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, water, nicotinamide adenine dinucleotide phosphate, potassium hydroxide in methanol, toluene Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys 32 %Chromat.

With 12-molybdophosphoric acid HPMo, oxygen, tetra-n-butylammonium acetate, palladium diacetate in ethyl acetate, Time= 1h, T= 100 °C , p= 22502.3Torr Dornan, Laura M.; Muldoon, Mark J.; Catalysis Science and Technology; vol. 5; nb. 3; (2015); p. 1428 - 1432 View in Reaxys

Rx-ID: 35100987 View in Reaxys 6/502 Yield

Conditions & References

56 %, 35 % With tetrafluoroboric acid, oxygen, palladium diacetate, p-benozquinone 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 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-β-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:

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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: δ 200.8, 136.9, 132.9, 128.5, 128.0, 31.8, 8.2. B: 1H NMR: δ 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: δ 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-benozquinone 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 K+ -1 O O

N N

(v4)

Rx-ID: 31719349 View in Reaxys 7/502 Yield 65 %

Conditions & References General procedure for the reactions of borate 2a with diazo compounds 6. General procedure: TMSCl (140 μL, 1.1 mmol) or TMSOTf (200 μL, 1.1 mmol) was added to a solution of borate 2a (284 mg, 1.1 mmol) in 1,2-DME (1.5 mL) at -20 °C, and the temperature was allowed to warm to -10 °C over 20 min. The mixture was again cooled to -20 °C, diazo compound 6 (1 mmol) and MeOH (49 μL, 1.2 mmol) were added [in the case of ethyl diazopropionate (6d) the reaction was carried out without MeOH], and the temperature was allowed to warm to 0 °C over 1 h. The cooling bath was removed, and the mixture stirred at room temperature for the time indicated in Table 4. The work-up was the same as that used in the procedure with EDA. Stage 1: With chloro-trimethyl-silane in ethylene glycol dimethyl ether, Time= 0.333333h, T= -20 - -10 °C , Inert atmosphere Stage 2: With methanol in ethylene glycol dimethyl ether, Time= 3h, T= -20 - 20 °C , Inert atmosphere Elkin, Pavel K.; Levin, Vitalij V.; Dilman, Alexander D.; Struchkova, Marina I.; Belyakov, Pavel A.; Arkhipov, Dmitry E.; Korlyukov, Alexander A.; Tartakovsky, Vladimir A.; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5259 - 5263 View in Reaxys

Rx-ID: 1548754 View in Reaxys 8/502 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

22 %, 68 % With water, Aliquatreg; 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 1-phenyl-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. 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).

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; 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, [AuMe(PPh3)], 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 % Chro- With [HBMes2]2, dihydrogen peroxide, 1) THF, 60 min, 25 deg C, 2) THF - NaH2PO4 buffer, Yields of byproduct given. mat. 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 [HBMes2]2, 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 % Chro- With sodium hydroxide, lithium borohydride, dihydrogen peroxide, ethyl acetate, different ratios, Product distribution mat., 24 % Brown, Herbert C.; Somayaji, Vishwanatha; Narasimhan, S.; Journal of Organic Chemistry; vol. 49; nb. 25; (1984); Chromat. 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 palladous 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, [Au(PPh3)2]PF6, 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 lauryl 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 %Chro- With water, bis-(trifluoromethylsulphonyl)amine in 1,4-dioxane, Time= 20h, T= 80 °C , Concentration, regioselective mat., 66 reaction %Chromat. Cabrero-Antonino, Jose R.; Leyva-Perez, Antonio; Corma, Avelino; Chemistry - A European Journal; vol. 19; nb. 26; (2013); p. 8627 - 8633 View in Reaxys O O

N O

Rx-ID: 1986974 View in Reaxys 9/502 Yield

Conditions & References

88 %

With sodium hypophosphite, nickel in ethanol, water, Time= 2h, T= 40 - 60 °C Monti, Diego; Gramatica, Paola; Speranza, Giovanna; Manitto, Paolo; Tetrahedron Letters; vol. 24; nb. 4; (1983); p. 417 - 418 View in Reaxys

82 %

With water, magnesium, tin(ll) chloride in tetrahydrofuran, Time= 0.25h, Ambient temperature Das, Nalin B.; Sarangi, Chintamani; Nanda, Bhagabat; Nayak, Amalendu; Sharma, Ram P.; Journal of Chemical Research - Part S; nb. 1; (1996); p. 28 - 29 View in Reaxys

80 %

With L-Selectridereg; in tetrahydrofuran, Time= 0.5h Mourad, M. Soubei; Varma, Rajender S.; Kabalka, George W.; Synthesis; nb. 6/7; (1985); p. 654 - 656 View in Reaxys

racemate

Rx-ID: 1764009 View in Reaxys 10/502 Yield 57 %

Conditions & References With iodosylbenzene, 5,5'-dinitro-N,N'-ethylenebis(salicylideneaminato) manganese(III)(hexafluorophosphate) in acetonitrile, T= 25 °C Srinivasan, K.; Michaud, P.; Kochi, J. K.; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2309 - 2320 View in Reaxys

O N

Rx-ID: 2040170 View in Reaxys 11/502

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Yield

Conditions & References

98 %

Stage 1: With trimethylphosphane in tetrahydrofuran, Time= 0.25h, T= 20 °C Stage 2: With water in tetrahydrofuran, Time= 0.0833333h, T= 20 °C , Further stages. Bures, Jordi; Vilarrasa, Jaume; Tetrahedron Letters; vol. 49; nb. 3; (2008); p. 441 - 444 View in Reaxys

85 %

With hydrogenchloride, iron in methanol, water, Time= 0.5h, Heating Pradhan, Prasun K.; Dey, Sumit; Jaisankar, Parasuraman; Giri, Venkatachalam S.; Synthetic Communications; vol. 35; nb. 7; (2005); p. 913 - 922 View in Reaxys

17 %

With glucose-6-phosphate dehydrogenase, glucose-6-phosphate, nicotinamide adenine dinucleotide phosphate, Time= 24h, T= 30 °C , pH= 7.5, aq. buffer Durchschein, Katharina; Ferreira-Da Silva, Bianca; Wallner, Silvia; MacHeroux, Peter; Kroutil, Wolfgang; Glueck, Silvia Maria; Faber, Kurt; Green Chemistry; vol. 12; nb. 4; (2010); p. 616 - 619 View in Reaxys With chloro-trimethyl-silane, 1,8-diazabicyclo[5.4.0]undec-7-ene, 3-chloro-benzenecarboperoxoic acid, 1.) dichloromethane, 30 min, 0 degC; 2.) dichloromethane, 30 min, room temperature, Yield given. Multistep reaction Aizpurus, J. M.; Oiarbide, M.; Palomo, C.; Tetrahedron Letters; vol. 28; nb. 44; (1987); p. 5361 - 5364 View in Reaxys With sodium hydroxide, sulfuric acid, 1.) ethanol, room temperature, 5 min, 2.) n-pentane, 0 deg C, 1 h, Yield given. Multistep reaction Chikashita, H.; Morita, Y.; Itoh, K.; Synthetic Communications; vol. 17; nb. 6; (1987); p. 677 - 684 View in Reaxys

81 % Chro- Stage 1: With sodium methylate in methanol, Time= 0.5h mat. Stage 2: in methanol, T= 10 - 15 °C , Electrolysis Ogibin; Ilovaiskii; Merkulova; Terent'ev; Nikishin; Russian Chemical Bulletin; vol. 51; nb. 8; (2002); p. 1460 - 1465 View in Reaxys Reaction Steps: 2 1: potassium tert-butoxide, 18-crown-6 / ethanol 2: protonated concave pyridine 8*H+ / ethanol / 15 h / 0.11 M concave pyridine 8/0.03 M TosOH buffer; other proton sources, other sec. nitronate anions With 18-crown-6 ether, protonated concave pyridine 8*H+, potassium tert-butylate in ethanol Luening, Ulrich; Schillinger, Fritz; Chemische Berichte; vol. 123; nb. 10; (1990); p. 2073 - 2075 View in Reaxys

racemate

Rx-ID: 4754852 View in Reaxys 12/502 Yield 90 %

Conditions & References With (tetraphenylporphinato)Fe(ClO4) in 1,4-dioxane, Time= 2.5h, T= 80 °C Takanami, Toshikatsu; Hirabe, Rina; Ueno, Masayoshi; Hino, Fumio; Suda, Kohji; Chemistry Letters; nb. 12; (1996); p. 1031 - 1032 View in Reaxys

82 %

With [Pd2H2(1,3-bis(diphenylphosphino)propane)3](TfO)2 in tetrahydrofuran, Time= 12h, T= 85 °C , Schlenk technique, Inert atmosphere, Glovebox Vyas, Devendra J.; Larionov, Evgeny; Besnard, Celine; Guenee, Laure; Mazet, Clement; Journal of the American Chemical Society; vol. 135; nb. 16; (2013); p. 6177 - 6183

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View in Reaxys 77 %

With bismuth trifluoromethanesulphonate in dichloromethane, Time= 1h Bhatia, Kaushik A.; Eash, Kyle J.; Leonard, Nicholas M.; Oswald, Matthew C.; Mohan, Ram S.; Tetrahedron Letters; vol. 42; nb. 46; (2001); p. 8129 - 8132 View in Reaxys

70 %

With bismuth oxide perchlorate in dichloromethane, Time= 0.75h, T= 20 °C , Rearrangement Anderson, Andrew M.; Blazek, Jesse M.; Garg, Parie; Payne, Brian J.; Mohan, Ram S.; Tetrahedron Letters; vol. 41; nb. 10; (2000); p. 1527 - 1530 View in Reaxys

25 %

in acetonitrile, Time= 1h, Photolysis Linder, Sorana; White, Katherine; Palmer, Mandelin; Arney, Benny; White, Rick; Tetrahedron Letters; vol. 43; nb. 7; (2002); p. 1169 - 1170 View in Reaxys With Ir(III) chloride in tetrahydrofuran, Time= 2h, T= 50 °C , Meinwald rearrangement Karame, Iyad; Tommasino, M. Lorraine; Lemaire, Marc; Tetrahedron Letters; vol. 44; nb. 41; (2003); p. 7687 - 7689 View in Reaxys

Rx-ID: 9068833 View in Reaxys 13/502 Yield 100 %

Conditions & References With mercuric triflate, water, N,N,N',N'-tetramethyl-urea in dichloromethane, acetonitrile, Time= 12h, T= 20 °C Nishizawa, Mugio; Skwarczynski, Mariusz; Imagawa, Hiroshi; Sugihara, Takumichi; Chemistry Letters; nb. 1; (2002); p. 12 - 13 View in Reaxys

91 %

With sulfuric acid, water, Time= 7h, T= 100 °C Zhu, Fengxia; Zhang, Fang; Yang, Xushi; Huang, Jianlin; Li, Hexing; Journal of Molecular Catalysis A: Chemical; vol. 336; nb. 1-2; (2011); p. 1 - 7 View in Reaxys

82 %

With water, zirconium tetrachloride, butan-1-ol, [Ir(1,5-cyclooctadiene)2]PF6, methyl-ethyl phosphite, Time= 15h, T= 70 °C Hirabayashi, Tomotaka; Okimoto, Yoshio; Saito, Akiyo; Morita, Masao; Sakaguchi, Satoshi; Ishii, Yasutaka; Tetrahedron; vol. 62; nb. 10; (2006); p. 2231 - 2234 View in Reaxys

62 %

With methanol, platinum (II) chloride, Time= 23h, T= 70 °C , Inert atmosphere 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 With methanol, [Au(PPh3)2]PF6, sulfuric acid in water, Time= 10h, T= 100 °C , Inert atmosphere, Sealed tube, regiospecific reaction 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

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Rx-ID: 306045 View in Reaxys 14/502 Yield

Conditions & References

92 %

With diethylzinc in dichloromethane, Time= 2h, T= 20 °C Li, Lezhen; Cai, Peijie; Guo, Qingxiang; Xue, Song; Journal of Organic Chemistry; vol. 73; nb. 9; (2008); p. 3516 3522 View in Reaxys With diethyl ether, silver nitrate Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 134; (1902); p. 847; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 185,186 View in Reaxys With Sodium bromate, sulfuric acid, sodium bromide in methanol, 1,2-dichloro-ethane, Time= 2h, T= 0 - 10 °C Agrawal, Manoj K.; Ghosh, Pushpito K.; Journal of Organic Chemistry; vol. 74; nb. 20; (2009); p. 7947 - 7950 View in Reaxys

Rx-ID: 2036901 View in Reaxys 15/502 Yield

Conditions & References

95 %

With methyltrichloromonosilane, sodium iodide in acetonitrile, Time= 1h, Ambient temperature Olah, George A.; Husain, Altaf; Singh, Brij P.; Mehrotra, Ashok K.; Journal of Organic Chemistry; vol. 48; nb. 21; (1983); p. 3667 - 3672 View in Reaxys

81 %

Moriarty, Robert M.; Khosrowshahi, Jaffar S.; Prakash, Om; Tetrahedron Letters; vol. 26; nb. 25; (1985); p. 2961 - 2964 View in Reaxys With hydrogenchloride Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu; Ikeda, Kaoru; Fujita, Tetsuhiro; Kamada, Tohru; Tetrahedron Letters; vol. 30; nb. 39; (1989); p. 5309 - 5312 View in Reaxys With trifluorormethanesulfonic acid, water, Yield given Okabe, Kazuaki; Ohwada, Tomohiko; Ohta, Toshiharu; Shudo, Koichi; Journal of Organic Chemistry; vol. 54; nb. 4; (1989); p. 733 - 734 View in Reaxys With water in dichloromethane, Ambient temperature, Yield given Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi; Tetrahedron; vol. 46; nb. 21; (1990); p. 7539 - 7555 View in Reaxys

O C

Rx-ID: 2697513 View in Reaxys 16/502

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Yield 75 %

Conditions & References With sodium hydroxide, pentacarbonyliron(0), tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, T= 10 °C , p= 10Torr Laurent, Pascale; Tanguy, Guy; Abbayes, Herve des; Journal of the Chemical Society, Chemical Communications; nb. 24; (1986); p. 1754 - 1756 View in Reaxys

Rx-ID: 555266 View in Reaxys 17/502 Yield 27 %

Conditions & References With pyridine, Time= 6h, Heating Jozwiak, Krzysztof; Khalid, Chakir; Tanga, Mary J.; Berzetei-Gurske, Ilona; Jimenez, Lucita; Kozocas, Joseph A.; Woo, Anthony; Zhu, Weizhong; Xiao, Rui-Ping; Abernethy, Darrell R.; Wainer, Irving W.; Journal of Medicinal Chemistry; vol. 50; nb. 12; (2007); p. 2903 - 2915 View in Reaxys

27 %

5 :[0132] Phenylacetone (35). A solution of 20.4 g (0.15 mol) of phenylacetic acid, acetic anhydride (70 mL) and pyridine (70 mL) was heated to reflux with stirring under argon atmosphere for 6 hours. Solvents were evaporated and residue dissolved in CHCl3 (100 mL), washed with IN NaOH (2 x 100 mL) and dried the organic layer (MgSO4), filtered, and evaporated to give 20.4 g. Vacuum distillation at 0.1 mm Hg in an oil bath set to 16O0C, followed by silica gel chromatography eluting with 1/1 hexanes/CH2Cl2 gave 5.5 g (27 percent). 1H (CDCl3) δ 2.15 (s, 3H), 3.70 (s, 2H), 7.20-7.36 (m, 5H). With pyridine, Time= 6h, Heating / reflux Patent; THE GOVERNMENT OF THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES; WO2008/22038; (2008); (A1) English View in Reaxys With sodium acetate Stoermer; Stroh; Chemische Berichte; vol. 68; (1935); p. 2112,2116 View in Reaxys Magidson; Garkuscha; Zhurnal Obshchei Khimii; vol. 11; (1941); p. 339,341; ; (1941); p. 5868 View in Reaxys Armellin, Silvia; Brenna, Elisabetta; Frigoli, Samuele; Fronza, Giovanni; Fuganti, Claudio; Mussida, Daniele; Analytical Chemistry; vol. 78; nb. 9; (2006); p. 3113 - 3117 View in Reaxys With 1-methyl-1H-imidazole, T= 20 °C , Inert atmosphere Chen, Jian; Zhang, Weicheng; Geng, Huiling; Li, Wei; Hou, Guohua; Lei, Aiwen; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 48; nb. 4; (2009); p. 800 - 802 View in Reaxys

Rx-ID: 1839925 View in Reaxys 18/502 Yield 1 % Chromat., 1 % Chromat., 68 %

Conditions & References With chromyl nitrate in tetrachloromethane, dichloromethane, N,N-dimethyl-formamide, Time= 0.5h, T= -78 °C 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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Rx-ID: 5093154 View in Reaxys 19/502 Yield

Conditions & References

58 % Chro- With water, RuCl2(C6H6)(PPh3) in ethanol, Time= 22h, T= 80 °C , Title compound not separated from byproducts mat., 4.3 % Tokunaga, Makoto; Wakatsuki, Yasuo; Angewandte Chemie - International Edition; vol. 37; nb. 20; (1998); p. 2867 Chromat. - 2869 View in Reaxys Stage 1: With 2,6-dimethylbenzeneamine, [(η5-cyclopentadienyl)2Ti(η2-Me3SiC2SiMe3)] in toluene, Time= 24h, T= 85 °C Stage 2: With hydrogenchloride, Title compound not separated from byproducts Tillack, Annegret; Jiao, Haijun; Castro, Ivette Garcia; Hartung, Christian G.; Beller, Matthias; Chemistry - A European Journal; vol. 10; nb. 10; (2004); p. 2409 - 2420 View in Reaxys

O O

Rx-ID: 29508995 View in Reaxys 20/502 Yield

Conditions & References

75 %

With copper(l) iodide, K3PO4*3H2O in dimethyl sulfoxide, Time= 20h, T= 90 °C , Inert atmosphere He, Chuan; Guo, Sheng; Huang, Li; Lei, Aiwen; Journal of the American Chemical Society; vol. 132; nb. 24; (2010); p. 8273 - 8275 View in Reaxys

1.8 g

1 : Step 1: Preparation of l-phenylpropanIntermediate E: Preparation of l-bro -3-phenylpropan-2-one Step 1: Preparation of l-phenylpropan- To a solution of iodobenzene (10.00 g, 49.02 mmol) in DMSO (150 mL) was added pentane-2,4-dione (14.72 g, 147.1 mmol), potassium phosphate (31.22 g, 147.1 mmol), water (7.95 g, 441.2 mmol) and copper(I) iodide (0.93 g, 4.90 mmol). The reaction then heated and kept at 90 °C overnight. After cooled to room temperature, 2 M aqueous HC1 (100 mL) was added into the reaction. The water phase was extracted with EtOAc (3 x 80 mL). The combined organics was washed with saturated aqueous NaCl (2 x 100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The resulting oil was purified by flash column chromatography to provide l-phenylpropan-2-one (1.8 g, 13.42 mmol) as light yellow oil. GCMS [M] = 134 With potassium phosphate, copper(l) iodide in water, dimethyl sulfoxide, T= 90 °C Patent; SUNOVION PHARMACEUTICALS INC.; NEWCOM, Jason, S.; SPEAR, Kerry, L.; WO2015/88565; (2015); (A1) English View in Reaxys

O C

Sn Br

Rx-ID: 2395336 View in Reaxys 21/502 Yield 88 %

Conditions & References With PdCl2bis(phenylimino)acenaphthene, fumaric acid dimethyl ester in N,N,N',N',N'',N''-hexamethylphosphoric triamide, Time= 20h, T= 20 °C , p= 825.07Torr Asselt, Rob van; Elsevier, Cornelis J.; Tetrahedron; vol. 50; nb. 2; (1994); p. 323 - 334 View in Reaxys

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Rx-ID: 37342867 View in Reaxys 22/502 Yield

Conditions & References

15 %Spectr.

Alkene substrate (0.1 mmol) and internal standard compound trimethylphenylsilicane(5 μL) were dissolved in CDCl3 (0.5 ml) in an NMR tube to record a 1H NMR. Then[RuIV(TDCPP)Cl2] (2.0 molpercent) and Cl2pyNO (1.03 equiv) were added and kept themixture at 60 oC. The progress of the reaction was monitored by 1H NMR. Afterdetermination of the product yield by 1H NMR spectroscopy, the product ketone wasseparated by flash chromatography on silica gel. With [RuIV(meso-tetrakis(2,6-dichlorophenyl)porphyrin)Cl2], 2,6-dichloropyridine-N-oxide in chloroform-d1, Time= 24h, T= 60 °C , Wacker Oxidation Wang, Zhi-Ming; Sang, Xue-Ling; Che, Chi-Ming; Chen, Jian; Tetrahedron Letters; vol. 55; nb. 10; (2014); p. 1736 - 1739 View in Reaxys

O O

Rx-ID: 1718716 View in Reaxys 23/502 Yield 89 %

Conditions & References With γ-picolinium chlorochromate in dichloromethane, Time= 11h, T= 20 °C Salehi; Khodaei; Goodarzi; Russian Journal of Organic Chemistry; vol. 38; nb. 11; (2002); p. 1671 - 1673 View in Reaxys

85 %

With pyridinium chlorochromate, Time= 2h, T= 50 °C Salehi; Firouzabadi; Farrokhi; Gholizadeh; Synthesis; nb. 15; (2001); p. 2273 - 2276 View in Reaxys

100 % Spectr.

With trimethylsilyl iodide in chloroform-d1, Time= 0.333333h, 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 racemate

racemate

Rx-ID: 2005274 View in Reaxys 24/502 Yield

Conditions & References

3 %, 11 %, With pyridine 1-oxide, oxochromium(V) complex of tetramethylsalen IIb in acetonitrile 4 %, 55 % Samsel, E. G.; Srinivasan, K.; Kochi, J. K.; Journal of the American Chemical Society; vol. 107; nb. 25; (1985); p. 7606 - 7617 View in Reaxys 18 %, 8.0 %, 8.4 %, 15 %

With iodosylbenzene, Ni(cyclam)(NO3)2 in acetonitrile, Time= 5h, Ambient temperature, Further byproducts given

15 %, 8.0 %, 8.4 %, 18 %

With iodosylbenzene, Ni(cyclam)(NO3)2 in acetonitrile, Time= 5h, Ambient temperature, Further byproducts given

Kinneary, Joanne F.; Albert, Jeffrey S.; Burrows, Cynthia J.; Journal of the American Chemical Society; vol. 110; nb. 18; (1988); p. 6124 - 6129 View in Reaxys

Kinneary, Joanne F.; Albert, Jeffrey S.; Burrows, Cynthia J.; Journal of the American Chemical Society; vol. 110; nb. 18; (1988); p. 6124 - 6129

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View in Reaxys 18 %, 8.0 %, 15 %, 8.4 %

With iodosylbenzene, Ni(cyclam)(NO3)2 in acetonitrile, Time= 5h, Ambient temperature, Further byproducts given Kinneary, Joanne F.; Albert, Jeffrey S.; Burrows, Cynthia J.; Journal of the American Chemical Society; vol. 110; nb. 18; (1988); p. 6124 - 6129 View in Reaxys

Rx-ID: 2039650 View in Reaxys 25/502 Yield 89 %

Conditions & References With titanium tetrachloride Sato, Mitsuyoshi; Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Tetrahedron Letters; vol. 22; nb. 17; (1981); p. 1609 - 1612 View in Reaxys

89 %

With titanium tetrachloride in dichloromethane, water, T= 25 °C Takai; Sato; Oshima; Nozaki; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 108 - 115 View in Reaxys

Rx-ID: 2696945 View in Reaxys 26/502 Yield 68 %

Conditions & References With nickel in ethylene glycol dimethyl ether, Time= 0.25h, T= 85 °C Inaba, Shin-ichi; Rieke, Reuben D.; Tetrahedron Letters; vol. 24; nb. 24; (1983); p. 2451 - 2452 View in Reaxys Inaba, Shin-ichi; Rieke, Reuben D.; Journal of Organic Chemistry; vol. 50; nb. 9; (1985); p. 1373 - 1381 View in Reaxys

63 %Chromat.

With Ni(bpy)(CH3SO3)2 in N,N-dimethyl-formamide, T= 20 °C , Ionic liquid, Electrochemical reaction Barhdadi, Rachid; Maekawa, Hirofumi; Comminges, Clement; Troupel, Michel; Bulletin of the Chemical Society of Japan; vol. 82; nb. 12; (2009); p. 1510 - 1513 View in Reaxys

O Br

Rx-ID: 3346413 View in Reaxys 27/502 Yield 62 %

Conditions & References With (bpy)NiBr2, tetra-n-butylammonium tetrafluoroborate in N,N-dimethyl-formamide, T= 70 °C , i = 250 mA, nickelsponge cathode Durandetti, Muriel; Nedelec, Jean-Yves; Perichon, Jacques; Journal of Organic Chemistry; vol. 61; nb. 5; (1996); p. 1748 - 1755 View in Reaxys

54 %

With (bpy)NiBr2, tetra-n-butylammonium tetrafluoroborate, T= 80 °C , Al rod/nickel-sponge, electrolysis Durandetti; Sibille; Nedelec; Perichon; Synthetic Communications; vol. 24; nb. 2; (1994); p. 145 - 151 View in Reaxys

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With NiBr2(PPh3)2 in tetrahydrofuran, electrochem. synthesis; electrodes: SCE/Hg, -1.2 V; electrolyte: 0.3 M LiClO4, Yield given Folest, J. C.; Perichon, J.; Fauvarque, J. F.; Jutand, A.; Journal of Organometallic Chemistry; vol. 342; (1988); p. 259 - 262 View in Reaxys

Rx-ID: 3978075 View in Reaxys 28/502 Yield

Conditions & References

72 %

With hydrogenchloride, bis-triphenylphosphine-palladium(II) chloride in toluene, Time= 20h, T= 80 °C Kosugi, Masanori; Sumiya, Takashi; Obara, Yukimasa; Suzuki, Motohiro; Sano, Hiroshi; Migita, Toshihiko; Bulletin of the Chemical Society of Japan; vol. 60; nb. 2; (1987); p. 767 - 768 View in Reaxys

Rx-ID: 5093155 View in Reaxys 29/502 Yield

Conditions & References

65 % Chromat., 7.0 % Chromat., 2.8 % Chromat.

With water, RuCl2(C6H6)(PPh2(C6F5)), diphenyl(pentafluorophenyl)phosphine in isopropyl alcohol, Time= 12h, T= 70

59 % Chromat., 2.2 % Chromat., 6.3 % Chromat.

With water, [(η6-C6H6)RuCl2], triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt in isopropyl alcohol, Time= 42h,

°C , Title compound not separated from byproducts Tokunaga, Makoto; Wakatsuki, Yasuo; Angewandte Chemie - International Edition; vol. 37; nb. 20; (1998); p. 2867 - 2869 View in Reaxys

T= 80 °C , Title compound not separated from byproducts Tokunaga, Makoto; Wakatsuki, Yasuo; Angewandte Chemie - International Edition; vol. 37; nb. 20; (1998); p. 2867 - 2869 View in Reaxys

O N

PhMgX

Rx-ID: 8737927 View in Reaxys 30/502 Yield 65 %

Conditions & References Stage 1: With copper(l) iodide, boron trifluoride diethyl etherate in tetrahydrofuran, T= -30 - 0 °C , Ring cleavage Stage 2: in tetrahydrofuran, Hydrolysis, Further stages. Hayes; Shipman; Twin; Chemical Communications; nb. 18; (2000); p. 1791 - 1792 View in Reaxys

Rx-ID: 9238947 View in Reaxys 31/502

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Yield

Conditions & References With Cu(2+), oxygen, anhydrous palladium, C88H144N30 in methanol, water, Time= 1h, T= 60 - 90 °C , p= 3750.38Torr ,

74 %, 8 %

Wacker oxidation Karakhanov; Maksimov; Runova; Kardasheva; Terenina; Kardashev; Skorkin; Karapetyan; Talanova; Russian Chemical Bulletin; vol. 57; nb. 4; (2008); p. 780 - 792 View in Reaxys 35 %, 53 % With methanesulfonic acid, molybdovanadophosphate, oxygen, Pd(OAc)2 on carbon, ammonium chloride in ethanol, Time= 5.5h, T= 60 °C , Wacker-type oxidation Yokota, Takahiro; Sakakura, Aki; Tani, Masayuki; Sakaguchi, Satoshi; Ishii, Yasutaka; Tetrahedron Letters; vol. 43; nb. 49; (2002); p. 8887 - 8891 View in Reaxys

O Mg

Rx-ID: 25906754 View in Reaxys 32/502 Yield

Conditions & References 68.A :To a solution of N-methyl-N-methoxyacetamide (9.9mL. 97 mmol) in ether (300 mL) at 0°C was added benzylmagnesium chloride (97 mL a 1M solution in ether). The cloudy, white reaction mixture was warmed to room temperature for 2 h and then quenched by careful addition of 1N hydrochloric acid (100 mL). The organic phase was separated, washed with brine, dried over MgS04 and concentrated. The crude material was purified by column chromatography on silica gel eluting from 0-10percent EtOAc/hexane to give the title compound. 1H NMR (500 MHz, CDC13) : 6 7.36 (t, J =7. 1Hz, 2H), 7.30 (t, J = 7. 3Hz, 1H), 7.24 (d, J = 7. 3Hz, 2H), 3.72 (s, 2H), 2.18 (s, 3H). LC-MS: m/e 135 (M + H) + (1.95 min). Stage 1: in diethyl ether, Time= 2h, T= 0 - 20 °C Stage 2: With hydrochlorid acid in diethyl ether, water Patent; MERCK and CO., INC.; WO2003/87037; (2003); (A1) English View in Reaxys

Rx-ID: 26019901 View in Reaxys 33/502 Yield

Conditions & References

93 %

With diethylzinc in dichloromethane, Time= 2h, T= 20 °C Li, Lezhen; Cai, Peijie; Guo, Qingxiang; Xue, Song; Journal of Organic Chemistry; vol. 73; nb. 9; (2008); p. 3516 3522 View in Reaxys

H O N

O racemate

racemate

Rx-ID: 3194811 View in Reaxys 34/502 Yield

Conditions & References With hydrogen, boric acid, nickel in methanol, water, T= 0 °C Curran; Journal of the American Chemical Society; vol. 105; nb. 18; (1983); p. 5826 - 5833 View in Reaxys

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O E O

Rx-ID: 9771479 View in Reaxys 35/502 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 Cornell, Candace N.; Sigman, Matthew S.; Journal of the American Chemical Society; vol. 127; nb. 9; (2005); p. 2796 - 2797 View in Reaxys

O O

Rx-ID: 10494146 View in Reaxys 36/502 Yield

Conditions & References With manganese(II) fluoride, ZnF2, tri-tert-butyl phosphine, bis(dibenzylideneacetone)-palladium(0) in N,N-dimethylformamide, T= 70 °C Su, Weiping; Raders, Steven; Verkade, John G.; Liao, Xuebin; Hartwig, John F.; Angewandte Chemie - International Edition; vol. 45; nb. 35; (2006); p. 5852 - 5855 View in Reaxys

O Mg

O N

Rx-ID: 23143440 View in Reaxys 37/502 Yield

Conditions & References 62.A :To a solution of N-methyl-N-methoxyacetamide (9. 9mL. 97 mmol) in ether (300 ML) at 0°C was added benzylmagnesium chloride (97 mL a 1M solution in ether). The cloudy, white reaction mixture was warmed to room temperature for 2 h and then quenched by careful addition of IN hydrochloric acid (100 mL). The organic phase was separated, washed with brine, dried over MGS04 and concentrated. The crude material was purified by column chromatography on silica gel eluting from 0-10percent EtOAc/hexane to give the title compound. 1H NMR (500 MHz, CDC13) : 8 7.36 (t, J = 7. lHz, 2H), 7.30 (t, J = 7.3Hz, 1H), 7.24 (d, J = 7.3Hz, 2H), 3.72 (s, 2H), 2.18 (s, 3H). LC-MS: M/E 135 (M + H) + (1.95 min). in diethyl ether, Time= 2h, T= 0 - 20 °C Patent; MERCK and CO., INC.; WO2005/27837; (2005); (A2) English View in Reaxys 32.A : REFERENCE EXAMPLE 32; 4- (4-METHYLPHENYL)-3-PHENYLBUTAN-2-AMINE (mixture of 4 isomers); Step A; 1-Phenylacetone To a solution of N-methyl-N-methoxyacetamide (9.9mL. 97 mmol) in ether (300 mL) at 0C was added benzylmagnesium chloride (97 mL a 1M solution in ether). The cloudy, white reaction mixture was warmed to room temperature for 2 h and then quenched by careful addition of IN hydrochloric acid (100 mL). The organic phase was separated, washed with brine, dried over MGS04 and concentrated. The crude material was purified by column chromatography on silica gel eluting from 0-10percent EtOAc/hexane to give the title compound. 1H NMR (500 MHz, CDC13) : 6 7.36 (t, J =7. 1HZ, 2H), 7.30 (t, J = 7. 3Hz, 1H), 7.24 (d, J = 7. 3Hz, 2H), 3.72 (s, 2H), 2.18 (s, 3H). LC-MS: M/E 135 (M + H) + (1. 95 MIN). in diethyl ether, Time= 2h, T= 0 - 20 °C , Acidic aqueous solution Patent; MERCK and CO., INC.; WO2004/48317; (2004); (A1) English View in Reaxys

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62.A :REFERENCE EXAMPLE 62 4-(4-Methylphenyl)-3-phenelbutan-2-amine (mixture of 4 isomers) Step A 1-Phenylacetone To a solution of N-methyl-N-methoxyacetamide (9. 9mL. 97 mmol) in ether (300 mL) at 0°C was added benzylmagnesium chloride (97 mL a 1M solution in ether). The cloudy, white reaction mixture was warmed to room temperature for 2 h and then quenched by careful addition of IN hydrochloric acid (100 mL). The organic phase was separated, washed with brine, dried over MgS04 and concentrated. The crude material was purified by column chromatography on silica gel eluting from 0-10percent EtOAc/hexane to give the title compound. in diethyl ether, Time= 2h, T= 0 - 20 °C Patent; MERCK and CO., INC.; WO2005/44785; (2005); (A1) English View in Reaxys

Rx-ID: 38471071 View in Reaxys 38/502 Yield

Conditions & References

80 %

With tetra-n-butylammonium acetate, palladium diacetate, HSA in toluene, Time= 6h, T= 100 °C , p= 22502.3Torr Dornan, Laura M.; Clendenning, Grainne M. A.; Pitak, Mateusz B.; Coles, Simon J.; Muldoon, Mark J.; Catalysis Science and Technology; vol. 4; nb. 8; (2014); p. 2526 - 2534 View in Reaxys

O S NH O

Rx-ID: 2139400 View in Reaxys 39/502 Yield

Conditions & References

91 %

With Amberlyst 15 in water, acetone, Time= 24h, Ambient temperature Ballini, Roberto; Petrini, Marino; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2563 - 2566 View in Reaxys

74 %

With Envirocat EPZG in water, acetone, Time= 5h, T= 80 °C Ballini, Roberto; Bosica, Giovanna; Maggi, Raimondo; Sartori, Giovanni; Synlett; vol. 1997; nb. 7; (1997); p. 795 - 796 View in Reaxys

Rx-ID: 2360059 View in Reaxys 40/502 Yield 80 %

Conditions & References With tetra-(n-butyl)ammonium iodide in N,N-dimethyl-formamide, T= 0 - 10 °C , electrolysis d'Incan, Esther; Sibille, Soline; Perichon, Jacques; Moingeon, Marie-Odile; Chaussard, Jacques; Tetrahedron Letters; vol. 27; nb. 35; (1986); p. 4175 - 4176 View in Reaxys

51 %Chromat.

With AlCl3, aluminium chloride, Ni(bpy)(CH3SO3)2 in N,N-dimethyl-formamide, Ionic liquid, Electrochemical reaction Barhdadi, Rachid; Maekawa, Hirofumi; Comminges, Clement; Troupel, Michel; Bulletin of the Chemical Society of Japan; vol. 82; nb. 12; (2009); p. 1510 - 1513 View in Reaxys

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Rx-ID: 2817696 View in Reaxys 41/502 Yield

Conditions & References

93 %

With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Time= 1h, T= 0 °C Citterio, Attilio; Gandolfi, Marco; Giordano, Claudio; Castaldi, Graziano; Tetrahedron Letters; vol. 26; nb. 13; (1985); p. 1665 - 1666 View in Reaxys

Rx-ID: 3743141 View in Reaxys 42/502 Yield

Conditions & References

21 %, 17 % With copper(l) iodide, caesium carbonate in acetonitrile, Time= 12h, T= 90 °C , Schlenk technique Xing, Qi; Lv, Hui; Xia, Chungu; Li, Fuwei; Chemistry - A European Journal; vol. 21; nb. 23; (2015); p. 8591 - 8596 View in Reaxys 65 % Chro- With potassium carbonate, copper(l) iodide in dimethyl sulfoxide, Time= 4h, T= 120 °C mat., 11 % Okuro, Kazumi; Furuune, Makoto; Miura, Masahiro; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 58; Chromat. nb. 26; (1993); p. 7606 - 7607 View in Reaxys 11 % Chro- With potassium carbonate, copper(l) iodide in dimethyl sulfoxide, Time= 4h, T= 120 °C mat., 65 % Okuro, Kazumi; Furuune, Makoto; Miura, Masahiro; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 58; Chromat. nb. 26; (1993); p. 7606 - 7607 View in Reaxys With copper ferrite, potassium carbonate in dimethyl sulfoxide, Time= 3h, T= 140 °C , Inert atmosphere, Temperature, Solvent, Concentration, Reagent/catalyst Nguyen, Anh T.; Nguyen, Lan T. M.; Nguyen, Chung K.; Truong, Thanh; Phan, Nam T. S.; ChemCatChem; vol. 6; nb. 3; (2014); p. 815 - 823 View in Reaxys

O O

Rx-ID: 3944234 View in Reaxys 43/502 Yield

Conditions & References

92 %

With Co(CO)8 in methanol, Time= 24h, T= 40 °C Prandi; Namy; Menoret; Kagan; Journal of Organometallic Chemistry; vol. 285; nb. 1-3; (1985); p. 449 - 460 View in Reaxys

racemate

Rx-ID: 8582528 View in Reaxys 44/502 Yield 75 %

Conditions & References With bismuth trifluoromethanesulphonate in dichloromethane, Time= 1h

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Bhatia, Kaushik A.; Eash, Kyle J.; Leonard, Nicholas M.; Oswald, Matthew C.; Mohan, Ram S.; Tetrahedron Letters; vol. 42; nb. 46; (2001); p. 8129 - 8132 View in Reaxys 70 %

O C

E O

Rx-ID: 32026254 View in Reaxys 45/502 Yield

Conditions & References

77 %, 5 With palladium diacetate, 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile, Time= 24h, T= 50 °C , p= %Chromat. 760.051Torr , regioselective reaction Chen, Huoji; Cai, Congbi; Liu, Xiaohang; Li, Xianwei; Jiang, Huanfeng; Chemical Communications; vol. 47; nb. 44; (2011); p. 12224 - 12226 View in Reaxys 8 %ChroWith palladium diacetate, 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile, T= 50 °C , p= 760.051Torr , regiomat., 66 selective reaction %Chromat. Chen, Huoji; Cai, Congbi; Liu, Xiaohang; Li, Xianwei; Jiang, Huanfeng; Chemical Communications; vol. 47; nb. 44; (2011); p. 12224 - 12226 View in Reaxys

Si O

Rx-ID: 37710833 View in Reaxys 46/502 Yield 64 %

Conditions & References With C6H14BNO*C2HF6NO4S2 in dichloromethane, Time= 0.5h, T= -40 °C Kang, Byung Chul; Shim, Su Yong; Ryu, Do Hyun; Organic Letters; vol. 16; nb. 8; (2014); p. 2077 - 2079 View in Reaxys

Z racemate

racemate

Rx-ID: 2005278 View in Reaxys 47/502 Yield 2 %, 8 %, 46 %

46 %, 2 %, With iodosylbenzene, 5,5'-dinitro-N,N'-ethylenebis(salicylideneaminato) manganese(III)(hexafluorophosphate) in ace8% tonitrile, T= 25 °C Srinivasan, K.; Michaud, P.; Kochi, J. K.; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2309 - 2320 View in Reaxys With iodosylbenzene, lt;(5,5'-(NO2)2salen)Mngt;(1+)*PF6 (1-) in acetonitrile, T= 25 °C , stereospecificity in the epoxidation catalyzed by various (salen)MnIII complexes; various olefins investigated, Product distribution

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Srinivasan, K.; Michaud, P.; Kochi, J. K.; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2309 - 2320 View in Reaxys

Z N O

Rx-ID: 2125436 View in Reaxys 48/502 Yield 82 %

Conditions & References With hydrogenchloride, iron in methanol, water, Time= 0.5h, Heating Pradhan, Prasun K.; Dey, Sumit; Jaisankar, Parasuraman; Giri, Venkatachalam S.; Synthetic Communications; vol. 35; nb. 7; (2005); p. 913 - 922 View in Reaxys

80 %

With formaldehyd in 1,4-dioxane, perchloric acid, dichloromethane, Time= 0.333333h, Ambient temperature Torii, Sigeru; Tanaka, Hideo; Katoh, Tetsuo; Chemistry Letters; (1983); p. 607 - 610 View in Reaxys

80 %

With water, magnesium, cadmium (II) chloride in tetrahydrofuran, Time= 0.25h, Ambient temperature Bordoloi, Manobjyoti; Journal of the Chemical Society, Chemical Communications; nb. 11; (1993); p. 922 - 923 View in Reaxys

76 %

With aluminium, nickel dichloride in tetrahydrofuran, Substitution Bezbarua, Maitreyee S.; Bez, Ghanashyam; Barua, Nabin C.; Chemistry Letters; nb. 4; (1999); p. 325 - 326 View in Reaxys

O N O

Rx-ID: 3916951 View in Reaxys 49/502 Yield 85 %

Conditions & References With trifluorormethanesulfonic acid in dichloromethane, Time= 0.0166667h, T= -40 °C Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi; Tetrahedron; vol. 46; nb. 21; (1990); p. 7539 - 7555 View in Reaxys

HO H

Rx-ID: 5195147 View in Reaxys 50/502 Yield 66 %

Conditions & References With (1R)-N-oxyl-1-(N-benzylcarbamoyl)-8-azabicyclo[3.2.1]octane, sodium hydrogencarbonate, sodium bromide in dichloromethane, water, T= 0 °C , Electrochemical reaction, optical yield given as percent ee, enantioselective reaction Demizu, Yosuke; Shiigi, Hirofumi; Mori, Hiroyuki; Matsumoto, Kazuya; Onomura, Osamu; Tetrahedron Asymmetry; vol. 19; nb. 23; (2008); p. 2659 - 2665 View in Reaxys

40 %

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

44 % Chro- With Geotrichum candidum IFO 4597 cells on BL-100 polymer, cyclohexanone in hexane, Time= 24h, T= 30 °C , mat. Oxidation

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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 50.9 % Chromat.

With air, (R,R)-(nitroso)(salen)ruthenium(II) chloride in toluene, Time= 17h, T= 20 °C , Irradiation, resolution of racemate; oxidation Masutani, Kouta; Uchida, Tatsuya; Irie, Ryo; Katsuki, Tsutomu; Tetrahedron Letters; vol. 41; nb. 26; (2000); p. 5119 - 5123 View in Reaxys With [bis(acetoxy)iodo]benzene, tetraethylammonium bromide, [Mn{CHPhNCH[OC6H2(t-Bu)2]}2]PF6 in water, Time= 0.5h, T= 20 °C , Product distribution, Further Variations: Catalysts, reaction times Sun, Wei; Wang, Hongwang; Xia, Chungu; Li, Jingwei; Zhao, Peiqing; Angewandte Chemie - International Edition; vol. 42; nb. 9; (2003); p. 1042 - 1044 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 air, chiral Ru(salen)(nitrosyl) complex in chloroform, Time= 11h, T= 20 °C , UV-irradiation, Kinetics Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu; Tetrahedron; vol. 63; nb. 28; (2007); p. 6383 - 6387 View in Reaxys With air, chiral Ru(salen)(nitrosyl) complex in chloroform, T= 20 °C , UV-irradiation, Title compound not separated from byproducts. Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu; Tetrahedron; vol. 63; nb. 28; (2007); p. 6383 - 6387 View in Reaxys

O N Cl Mg

Rx-ID: 9073817 View in Reaxys 51/502 Yield

Conditions & References

65 %

With copper(l) iodide, boron trifluoride diethyl etherate in tetrahydrofuran, Time= 1h, T= -30 - 0 °C Hayes, Jerome F.; Shipman, Michael; Twin, Heather; Journal of Organic Chemistry; vol. 67; nb. 3; (2002); p. 935 942 View in Reaxys

OH S

Rx-ID: 11083193 View in Reaxys 52/502 Yield 87 %

Conditions & References With sulfuric acid in toluene, Time= 1h, T= 100 °C Yoshida, Suguru; Yorimitsu, Hideki; Oshima, Koichiro; Synlett; nb. 10; (2007); p. 1622 - 1624 View in Reaxys

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HO H

Rx-ID: 11097767 View in Reaxys 53/502 Yield

Conditions & References With [bis(acetoxy)iodo]benzene, potassium bromide in dichloromethane, water, Time= 1h, T= 20 °C Sun, Wei; Wu, Xiaomei; Xia, Chungu; Helvetica Chimica Acta; vol. 90; nb. 3; (2007); p. 623 - 626 View in Reaxys Stage 1: With C28H36ClMnN2O2, potassium acetate in dichloromethane, water, Time= 0.0833333h Stage 2: With N-bromosuccinmide in dichloromethane, water, Time= 2h, T= 20 °C , Kinetics, enantioselective reaction Xu, Daqian; Wang, Shoufeng; Shen, Zhiqiang; Xia, Chungu; Sun, Wei; Organic and Biomolecular Chemistry; vol. 10; nb. 14; (2012); p. 2730 - 2732 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. 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 , Reagent/catalyst 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

O Br

Rx-ID: 11113464 View in Reaxys 54/502 Yield 27 %

Conditions & References Stage 1: With potassium carbonate, bis(η3-allyl-μ-chloropalladium(II)), Tedicyp in N,N-dimethyl-formamide, Time= 20h, T= 130 °C , Heck reaction Stage 2: With hydrogenchloride, Further stages. Battace, Ahmed; Feuerstein, Marie; Lemhadri, Mhamed; Zair, Touriya; Doucet, Henri; Santelli, Maurice; European Journal of Organic Chemistry; nb. 19; (2007); p. 3122 - 3132 View in Reaxys 2H

Rx-ID: 41758399 View in Reaxys 55/502 Yield 48 %

Conditions & References Stage 1: With iodine, magnesium in tetrahydrofuran, Time= 1h, T= 25 °C Stage 2: in tetrahydrofuran, T= 0 - 20 °C Ge, Jing-Jie; Yao, Chuan-Zhi; Wang, Mei-Mei; Zheng, Hong-Xing; Kang, Yan-Biao; Li, Yadong; Organic Letters; vol. 18; nb. 2; (2016); p. 228 - 231

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View in Reaxys

Rx-ID: 277690 View in Reaxys 56/502 Yield

Conditions & References

70.8 %

With Ir(III) chloride, cerium(IV) sulphate, acetic acid in water, Time= 3h, T= 100 °C Tandon, Praveen K.; Srivastava, Manish; Singh, Santosh B.; Singh, Satpal; Synthetic Communications; vol. 38; nb. 13; (2008); p. 2125 - 2137 View in Reaxys With chromium oxychloride, Versetzen mit Wasser v. Miller; Rohde; Chemische Berichte; vol. 23; (1890); p. 1075 View in Reaxys

Rx-ID: 806750 View in Reaxys 57/502 Yield

Conditions & References

90 %

With indium(III) chloride in tetrahydrofuran, Time= 0.833333h, T= 25 °C , Rearrangement Ranu, Brindaban C.; Jana, Umasish; Journal of Organic Chemistry; vol. 63; nb. 23; (1998); p. 8212 - 8216 View in Reaxys

88 %

With epoxysulfonyl fluoride, Time= 0.833333h, T= 0 °C Kagan, Jacques; Agdeppa, Dalmacio A.; Chang, Arthur I.; Chen, Shyi-An; Harmata, Michael A.; et al.; Journal of Organic Chemistry; vol. 46; nb. 14; (1981); p. 2916 - 2920 View in Reaxys

82 %

With C45H104P6Pd2 in tetrahydrofuran, T= 85 - 140 °C Mazet, Clement; Chimia; vol. 67; nb. 9; (2013); p. 658 - 662 View in Reaxys T= 203 - 208 °C , p= 760Torr , inactive α-methyl-α'-phenyl-ethylene oxide from α-phenyl-α-propylene Fourneau; Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 662; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 140; (1905); p. 1595 View in Reaxys

Rx-ID: 3756850 View in Reaxys 58/502 Yield

Conditions & References With water-d2, pyridine, Time= 21h, T= 22 °C Thibblin, Alf; Journal of the American Chemical Society; vol. 111; nb. 14; (1989); p. 5412 - 5416 View in Reaxys

O 2H 2H 2H

2H 2H

Rx-ID: 8896083 View in Reaxys 59/502

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Yield

Conditions & References With water, oxygen, copper(l) iodide, palladium dichloride in N,N-dimethyl-formamide, 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

(methoxy)(2-methoxyl-1-phe‐ nyl)methylene pentacarbonyl chromium

bis-<1-phenyl-2-piperidino-propyl>-ether Rx-ID: 16038939 View in Reaxys 60/502

Yield

Conditions & References Reaction Steps: 2 1: [Cp2TiMe2] / toluene / 40 h / 100 °C 2: SiO2; H2O / CH2Cl2 With water, silica gel, bis(cyclopentadienyl)dimethyltitanium in dichloromethane, toluene, 1: Hydroamination / 2: Hydrolysis Haak, Edgar; Bytschkov, Igor; Doye, Sven; Angewandte Chemie - International Edition; vol. 38; nb. 22; (1999); p. 3389 - 3391 View in Reaxys

H O

Rx-ID: 1616763 View in Reaxys 61/502 Yield

Conditions & References With (NH4)2S2O8, copper diacetate 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

HO O

Rx-ID: 1623600 View in Reaxys 62/502 Yield 75 %

Conditions & References Stage 1: With copper (I) cyanide in diethyl ether, Time= 0.0833333h, T= 0 °C , Inert atmosphere Stage 2: in diethyl ether, Time= 15h, T= 0 - 20 °C , Inert atmosphere Genna, Douglas T.; Posner, Gary H.; Organic Letters; vol. 13; nb. 19; (2011); p. 5358 - 5361 View in Reaxys

62 %

With cerium(III) chloride in tetrahydrofuran, Time= 16h, T= -78 °C Ahn, Yoonmo; Cohen, Theodore; Tetrahedron Letters; vol. 35; nb. 2; (1994); p. 203 - 206 View in Reaxys With cerium(III) chloride, effect of CeCl3 quantity on yield of product, Product distribution Ahn, Yoonmo; Cohen, Theodore; Tetrahedron Letters; vol. 35; nb. 2; (1994); p. 203 - 206 View in Reaxys in diethyl ether, Time= 3h, T= 20 °C Hatzakis, Nikos S.; Smonou, Ioulia; Bioorganic Chemistry; vol. 33; nb. 4; (2005); p. 325 - 337 View in Reaxys

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H O

Rx-ID: 1839914 View in Reaxys 63/502 Yield

Conditions & References With (NH4)2S2O8, copper diacetate in water, acetonitrile, 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

N N N

Rx-ID: 2185924 View in Reaxys 64/502 Yield

Conditions & References

50 %

With NOBF4 in acetonitrile, Time= 0.0833333h, T= 0 °C Lorenzin, Michele; Guerriero, Antonio; Pietra, Francesco; Journal of Organic Chemistry; vol. 45; nb. 9; (1980); p. 1704 - 1705 View in Reaxys

Rx-ID: 2188730 View in Reaxys 65/502 Yield 94 %

Conditions & References With acetic acid, zinc, Time= 1h, T= 100 °C Tamura; Shindo; Uenishi; Ishibashi; Tetrahedron Letters; vol. 21; nb. 26; (1980); p. 2547 - 2548 View in Reaxys

94 %

With acetic acid, zinc, Time= 1h, T= 100 °C Tamura, Yasumitsu; Choi, Hong Dae; Mizutani, Masako; Ueda, Yuko; Ishibashi, Hiroyuki; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 10; (1982); p. 3574 - 3579 View in Reaxys

O HO OH

O O

Rx-ID: 2860179 View in Reaxys 66/502 Yield

Conditions & References

40 %, 14 % With oxygen, copper(l) chloride, palladium dichloride in ethylene glycol dimethyl ether Hosokawa, Takahiro; Ohta, Toshiyuki; Murahashi, Shun-Ichi; Journal of the Chemical Society, Chemical Communications; nb. 15; (1983); p. 848 - 849 View in Reaxys 40 %, 14 % With oxygen, copper(l) chloride, palladium dichloride in ethylene glycol dimethyl ether, Time= 20h, T= 50 °C Hosokawa, Takahiro; Ohta, Toshiyuki; Kanayama, Satoshi; Murahashi, Shun-Ichi; Journal of Organic Chemistry; vol. 52; nb. 9; (1987); p. 1758 - 1764 View in Reaxys

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Rx-ID: 4114203 View in Reaxys 67/502 Yield

Conditions & References

70 %, 12 % With KH2F3 in 1,2-dichloro-ethane, Time= 12h, T= 80 °C Tamura, Masanori; Shibakami, Motonari; Arimura, Takashi; Kurosawa, Shigeru; Sekiya, Akira; Journal of Fluorine Chemistry; vol. 70; nb. 1; (1995); p. 1 - 4 View in Reaxys 12 %, 70 % With KH2F3 in 1,2-dichloro-ethane, Time= 12h, T= 80 °C Tamura, Masanori; Shibakami, Motonari; Arimura, Takashi; Kurosawa, Shigeru; Sekiya, Akira; Journal of Fluorine Chemistry; vol. 70; nb. 1; (1995); p. 1 - 4 View in Reaxys

Al O

Rx-ID: 4378641 View in Reaxys 68/502 Yield

Conditions & References

75 %

With aluminium trichloride in dichloromethane Arisawa; Torisawa; Nakagawa; Synthesis; nb. 11; (1995); p. 1371 - 1372 View in Reaxys

72 %

Stage 1: With AlCl3, aluminium chloride in dichloromethane, T= -50 °C , Inert atmosphere Stage 2: in hexane, dichloromethane, T= -30 - 20 °C , Inert atmosphere Stage 3: With water in hexane, dichloromethane, T= 0 °C Maeda, Hajime; Nishitsuji, Nana; Mizuno, Kazuhiko; Research on Chemical Intermediates; vol. 36; nb. 5; (2010); p. 577 - 585 View in Reaxys

O N N O

Rx-ID: 4469842 View in Reaxys 69/502 Yield

Conditions & References

93 %

With copper acetylacetonate, tri-n-butyl-tin hydride in benzene, Time= 5h, Heating, Reduction Tan, Zhongping; Qu, Zhaohui; Chen, Bei; Wang, Jianbo; Tetrahedron; vol. 56; nb. 38; (2000); p. 7457 - 7461 View in Reaxys With potassium fluoride, tri-n-butyl-tin hydride, t-BuON=NOt-Bu, 1.) C6H6, 60 deg C, 0.5 h, 2.) Et2O, Yield given. Multistep reaction Dang, Hai-Shan; Roberts, Brian P.; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1996); p. 769 775 View in Reaxys

Rx-ID: 10229822 View in Reaxys 70/502 Yield

Conditions & References Stage 1: With copper(l) iodide in diethyl ether, Petroleum ether, cooling

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Stage 2: in diethyl ether, Petroleum ether, T= -78 °C , Further stages. Viswanathan, Rajesh; Prabhakaran, Erode N.; Plotkin, Michael A.; Johnston, Jeffrey N.; Journal of the American Chemical Society; vol. 125; nb. 1; (2003); p. 163 - 168 View in Reaxys

HO H

Rx-ID: 11275715 View in Reaxys 71/502 Yield

Conditions & References

23.1 % Chromat.

With NADH-H+, nicotinamide adenine dinucleotide, RE-ADH/LK-ADH in phosphate buffer, Time= 24h, T= 30 °C Gruber, Christian C.; Nestl, Bettina M.; Gross, Johannes; Hildebrandt, Petra; Bornscheuer, Uwe T.; Faber, Kurt; Kroutil, Wolfgang; Chemistry - A European Journal; vol. 13; nb. 29; (2007); p. 8271 - 8276 View in Reaxys With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in aq. buffer, T= 50 °C , pH= 8.9, Enzymatic reaction, Kinetics, Reagent/catalyst, enantiospecific reaction Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys 2.2.2. General procedure for mutant TeSADH-catalyzed racemization General procedure: Enantiopure alcohol (0.015 mmol), NADP+ (0.5 mg), NADPH (1.0 mg), mutant TeSADH (0.2 mg in Tris–HCl buffer solution, 50 mM, pH 8.0), Tris–HCl buffer solution (950 μL, 50 mM, pH 8.0), and acetonitrile (50 μL) were mixed in a 1.5-mL plastic tube. The reaction mixture was shaken at 50 °C and 200 rpm for 48 h, followed by extraction with ethyl acetate (2 × 500 μL). The combined organic layer was dried with sodium sulfate and concentrated to dryness. The remaining residue was treated with pyridine (two drops) and acetic anhydride (one drop) for 1 h to convert the alcohols to their corresponding acetates. The acetate products were diluted with CHCl3 prior to analysis on a GC equipped with a chiral column to determine ee. With NADPH, NADP+, W110G TeSADH in acetonitrile, T= 50 °C , pH= 8, Enzymatic reaction Musa, Musa M.; Patel, Jay M.; Nealon, Christopher M.; Kim, Chang Sup; Phillips, Robert S.; Karume, Ibrahim; Journal of Molecular Catalysis B: Enzymatic; vol. 115; (2015); p. 155 - 159 View in Reaxys

O N O

O N

O H

Rx-ID: 27925380 View in Reaxys 72/502 Yield , 27.7 %

Conditions & References With bis(norbornadiene)rhodium(I) tetrafluoroborate, hydrogen, (R,R)-Ph-BPE in dichloromethane, Time= 24h, T= 50 °C , p= 60804.1Torr , Autoclave, Reagent/catalyst, enantioselective reaction Li, Shengkun; Huang, Kexuan; Zhang, Xumu; Chemical Communications; vol. 50; nb. 64; (2014); p. 8878 - 8881 View in Reaxys With NADH-H+, hydrogen in phosphate buffer, 2,2,4-trimethylpentane, T= 30 °C , pH= 7.0, Title compound not separated from byproducts. Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298 View in Reaxys

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Rx-ID: 29647276 View in Reaxys 73/502 Yield

Conditions & References

54 %

Stage 1: With BF3*AcOH in dichloromethane, T= 0 - 20 °C , Inert atmosphere Stage 2: With potassium fluoride, dihydrogen peroxide, potassium hydrogencarbonate in tetrahydrofuran, methanol, water, T= 0 - 20 °C , Inert atmosphere, Tamao-Fleming oxidation Yonehara, Mitsuhiro; Nakamura, Shinji; Muranaka, Atsuya; Uchiyama, Masanobu; Chemistry - An Asian Journal; vol. 5; nb. 3; (2010); p. 452 - 455 View in Reaxys

O transtrans trans

H O

trans

Rx-ID: 32365099 View in Reaxys 74/502 Yield

Conditions & References

58 %, 42 % With tert.-butylhydroperoxide, .mu.-oxo-bis[dioxo-[(3'S,4'S)-2-(3',4'-dihydro-3'-phenyl-4'-methyloxy-methyl-2'-oxazolyl)pyridine-.kappa.2-N,N](isothiocyanato)molybdenum(VI)] in decane, dichloromethane, Time= 22h, T= 30 °C , Inert atmosphere, Ionic liquid Brito, Jose A.; Ladeira, Sonia; Teuma, Emmanuelle; Royo, Beatriz; Gomez, Montserrat; Applied Catalysis A: General; vol. 398; nb. 1-2; (2011); p. 88 - 95 View in Reaxys

Rx-ID: 35959380 View in Reaxys 75/502 Yield

Conditions & References With potassium phosphate, [Pd(η3-1-Ph-allyl)(μ-Cl)]2, (Mor-DalPhos) in 1,4-dioxane, tert-butyl alcohol, Time= 16h, T=

85 %

90 °C , Inert atmosphere, Glovebox, Reagent/catalyst, Solvent, Concentration Alsabeh, Pamela G.; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 52; nb. 28; (2013); p. 7242 - 7246; Angew. Chem.; vol. 125; nb. 28; (2013); p. 7383 - 7387 View in Reaxys

racemate

Rx-ID: 41533971 View in Reaxys 76/502 Yield 83 %

Conditions & References With [(N,N'-bis(3,5-di-tert-bytyl-salicylidene)-rac-1,2-cyclohexanediamine)Al(THF)2][Co(CO)4] in diethyl ether, Time= 18h, T= 20 °C Lamb, Jessica R.; Mulzer, Michael; Lapointe, Anne M.; Coates, Geoffrey W.; Journal of the American Chemical Society; vol. 137; nb. 47; (2015); p. 15049 - 15054 View in Reaxys

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O N O

Rx-ID: 1553477 View in Reaxys 77/502 Yield

Conditions & References

81 %

With chromium dichloride in tetrahydrofuran, hydrogenchloride, Time= 4h, Heating Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Tetrahedron Letters; vol. 26; nb. 32; (1985); p. 3777 3778 View in Reaxys

78 %

With tin(ll) chloride in tetrahydrofuran, Time= 0.25h, microwave irradiation Das, Deba D.; Nayak, Amalendu; Nanda, Bhagabat; Das, Nalin B.; Journal of Chemical Research; nb. 8; (2006); p. 481 - 482 View in Reaxys

Rx-ID: 1710228 View in Reaxys 78/502 Yield

Conditions & References

78 %

With tri-n-butyltin methoxide, bis (triortho-tolylphosphine)palladium(II) chloride in toluene, Time= 5h, T= 100 °C Kosugi, Masanori; Hagiwara, Isao; Sumiya, Takao; Migita, Toshihiko; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 241 - 246 View in Reaxys

78 %

With bis (triortho-tolylphosphine)palladium(II) chloride, tri-n-butyltin methoxide in toluene, Time= 5h, T= 100 °C Kosugi, Masanori; Hagiwara, Isao; Sumiya, Takashi; Migita, Toshihiko; Journal of the Chemical Society, Chemical Communications; nb. 7; (1983); p. 344 - 345 View in Reaxys

78 %

With tri-n-butyltin methoxide, bis (triortho-tolylphosphine)palladium(II) chloride in toluene, Time= 5h, T= 100 °C , var. Pd catalysts, Product distribution Kosugi, Masanori; Hagiwara, Isao; Sumiya, Takao; Migita, Toshihiko; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 241 - 246 View in Reaxys

H C–

Na +

Rx-ID: 1710641 View in Reaxys 79/502 Yield

Conditions & References

72 %

With copper(l) iodide in N,N-dimethyl-formamide, Time= 30h, T= 100 - 120 °C Sugai, Saburo; Ikawa, Hiroshi; Okazaki, Tokuji; Akaboshi, Sanya; Ikegami, Shiro; Chemistry Letters; (1982); p. 597 - 600 View in Reaxys

O racemate

Rx-ID: 1764004 View in Reaxys 80/502

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Yield

Conditions & References

4.0 %, 3.0 %, 60 %

With iodosylbenzene, Ni(cyclam)(NO3)2 in acetonitrile, Time= 5h, Ambient temperature Kinneary, Joanne F.; Albert, Jeffrey S.; Burrows, Cynthia J.; Journal of the American Chemical Society; vol. 110; nb. 18; (1988); p. 6124 - 6129 View in Reaxys

60 %, 3.0 %, 4 %

60 %, 3.0 %, 4.0 %

With iodosylbenzene, Ni-complex of 1,4,8,11-tetraazacyclotetradecane (1a) in acetonitrile, Time= 5h, Ambient temperature, Mechanism, Product distribution Kinneary, Joanne F.; Wagler, Thomas R.; Burrows, Cynthia J.; Tetrahedron Letters; vol. 29; nb. 8; (1988); p. 877 - 880 View in Reaxys

O– K+

Rx-ID: 2063722 View in Reaxys 81/502 Yield

Conditions & References

25 % Chromat., 25 % Chromat., 21 % Chromat.

With ammonia in tetrahydrofuran, T= -33 °C

21 % Chromat., 25 % Chromat., 25 % Chromat.

With ammonia, T= -33 °C

Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

O N

N N

Rx-ID: 2779781 View in Reaxys 82/502 Yield

Conditions & References

77 %

With hydrogenchloride in tetrahydrofuran, water, Time= 24h, Ambient temperature Katritzky, Alan R.; Yang, Zhijun; Lam, Jamshed N.; Journal of Organic Chemistry; vol. 56; nb. 24; (1991); p. 6917 - 6923 View in Reaxys

H O N

O racemate

racemate

Rx-ID: 3194810 View in Reaxys 83/502

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Yield

Conditions & References With hydrogen, boric acid, nickel in methanol, water Curran; Journal of the American Chemical Society; vol. 105; nb. 18; (1983); p. 5826 - 5833 View in Reaxys

Rx-ID: 3928531 View in Reaxys 84/502 Yield

Conditions & References

13 %

With tri-n-butyltin methoxide, bis (triortho-tolylphosphine)palladium(II) chloride in toluene, Time= 5h, T= 100 °C , three molar excess of the tin enolate Kosugi, Masanori; Hagiwara, Isao; Sumiya, Takao; Migita, Toshihiko; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 241 - 246 View in Reaxys

tributyltin methoxide, acetonyltributyltin

Rx-ID: 6046464 View in Reaxys 85/502 Yield

Conditions & References

78 %

With bis (triortho-tolylphosphine)palladium(II) chloride in toluene, Time= 5h, T= 100 °C Kosugi, Masanori; Suzuki, Mikio; Hagiwara, Isao; Goto, Katsuhisa; Saitoh, Kyoko; et al.; Chemistry Letters; (1982); p. 939 - 940 View in Reaxys

Rx-ID: 8556274 View in Reaxys 86/502 Yield

Conditions & References With Novozym 435, 2,6-dimethylheptan-4-ol, (Ph4C4CO)2H(μ-H)(CO)4Ru2 in toluene, Time= 110h, T= 70 °C , Enzymatic reaction, Reduction, Title compound not separated from byproducts. Jung, Hyun M.; Koh, Jeong H.; Kim, Mahn-Joo; Park, Jaiwook; Organic Letters; vol. 2; nb. 3; (2000); p. 409 - 411 View in Reaxys

O H

Rx-ID: 8556937 View in Reaxys 87/502 Yield

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(v2) (v2)

O O racemate

Rx-ID: 8819145 View in Reaxys 88/502 Yield

Conditions & References

58 %, 17 %, 17 %

Stage 1: in tetrahydrofuran, Time= 0.5h, T= 25 °C Stage 2: in tetrahydrofuran, Time= 0.5h, T= 25 °C Ukai; Oshima; Matsubara; Journal of the American Chemical Society; vol. 122; nb. 48; (2000); p. 12047 - 12048 View in Reaxys

Rx-ID: 26019900 View in Reaxys 89/502 Yield

Conditions & References

35 %, 60 % With Furukawa reagent in dichloromethane, Time= 2h, T= 20 °C Li, Lezhen; Cai, Peijie; Guo, Qingxiang; Xue, Song; Journal of Organic Chemistry; vol. 73; nb. 9; (2008); p. 3516 3522 View in Reaxys

O O

Rx-ID: 1616735 View in Reaxys 90/502 Yield

Conditions & References

14 %, 40 % With oxygen, ethylene glycol, copper(l) chloride, palladium dichloride in ethylene glycol dimethyl ether Hosokawa, Takahiro; Ohta, Toshiyuki; Murahashi, Shun-Ichi; Journal of the Chemical Society, Chemical Communications; nb. 15; (1983); p. 848 - 849 View in Reaxys 14 %, 40 % With oxygen, ethylene glycol, copper(l) chloride, palladium dichloride in ethylene glycol dimethyl ether, Time= 20h, T= 50 °C Hosokawa, Takahiro; Ohta, Toshiyuki; Kanayama, Satoshi; Murahashi, Shun-Ichi; Journal of Organic Chemistry; vol. 52; nb. 9; (1987); p. 1758 - 1764 View in Reaxys

H O O

Rx-ID: 1839913 View in Reaxys 91/502 Yield

Conditions & References With (NH4)2S2O8, 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

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Rx-ID: 2005254 View in Reaxys 92/502 Yield

Conditions & References

1 % Chromat., 3 % Chromat., 3 % Chromat., 73 % Chromat.

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

S O

Rx-ID: 2045640 View in Reaxys 93/502 Yield

Conditions & References

93 %

With zinc in acetic acid McKervey, M. Anthony; Ratananukul, Piniti; Tetrahedron Letters; vol. 24; nb. 1; (1983); p. 117 - 120 View in Reaxys

N N N

Rx-ID: 2138436 View in Reaxys 94/502 Yield

Conditions & References

34 %

With tris-(2-chloro-ethyl)-amine, aluminium trichloride in dichloromethane, Time= 17h, Ambient temperature, other catalyst Hassner, Alfred; Fibiger, Richard; Andisik, Donald; Journal of Organic Chemistry; vol. 49; nb. 22; (1984); p. 4237 - 4244 View in Reaxys

F O

HO racemate

Rx-ID: 2649931 View in Reaxys 95/502 Yield

Conditions & References

90 %

With silicon tetrafluoride, N-ethyl-N,N-diisopropylamine in 1,2-dichloro-ethane Shimizu, Makoto; Yoshioka, Hirosuke; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4101 - 4104 View in Reaxys

Rx-ID: 2815374 View in Reaxys 96/502 Yield 88 %

Conditions & References With hydrogenchloride in tetrahydrofuran, water, Time= 7h, Ambient temperature Syper, Ludwik; Tetrahedron; vol. 43; nb. 12; (1987); p. 2853 - 2872 View in Reaxys

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O N

N O

Rx-ID: 3916952 View in Reaxys 97/502 Yield

Conditions & References

55 %, 13 %, 17 %

With trifluorormethanesulfonic acid in dichloromethane, Time= 0.0166667h, T= -40 °C Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi; Tetrahedron; vol. 46; nb. 21; (1990); p. 7539 - 7555 View in Reaxys

55 %, 17 %, 13 %

OH O

Rx-ID: 3961499 View in Reaxys 98/502 Yield

Conditions & References

60 %

With 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, T= 25 °C Uemura, Sakae; Ohe, Kouichi; Sugita, Nobuyuki; Journal of the Chemical Society, Chemical Communications; nb. 2; (1988); p. 111 - 112 View in Reaxys

O Cl

O Sn

Rx-ID: 3967720 View in Reaxys 99/502 Yield 79 %

Conditions & References With bis-triphenylphosphine-palladium(II) chloride in benzene, react. mixt. washed (aq. KF); extn.of org. layer (ether); dried over MgSO4; product isolated by distn. (reduced pressure); acetonylated by chromy. (silica gel); GLC yield given Kosugi; Miyajima; Nakanishi; Sano; Migita; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3383 - 3385 ; (from Gmelin) View in Reaxys

79 %

With bis-triphenylphosphine-palladium(II) chloride in toluene, react. mixt. washed (aq. KF); extn.of org. layer (ether); dried over MgSO4; product isolated by distn. (reduced pressure); acetonylated by chromy. (silica gel); GLC yield given Kosugi; Miyajima; Nakanishi; Sano; Migita; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3383 - 3385 ; (from Gmelin) View in Reaxys With oxonium, bis-triphenylphosphine-palladium(II) chloride, 1.) THF, 120 deg C, Yield given. Multistep reaction Kosugi; Miyajima; Nakanishi; Sano; Migita; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3383 - 3385 View in Reaxys

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Rx-ID: 4033063 View in Reaxys 100/502 Yield

Conditions & References

32 %, 39 % With tris(trifluoroacetoxy)-λ3-iodane in tetrachloromethane, Time= 3h, T= 23 °C Futami; Nishino; Kurosawa; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3182 - 3186 View in Reaxys 39 %, 32 % With tris(trifluoroacetoxy)-λ3-iodane in tetrachloromethane, Time= 3h, T= 23 °C Futami; Nishino; Kurosawa; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3182 - 3186 View in Reaxys

N O

Rx-ID: 4900318 View in Reaxys 101/502 Yield 94 %

Conditions & References With water, oxalic acid in diethyl ether, Time= 4h, Ambient temperature Enders, Dieter; Hundertmark, Thomas; Lazny, Ryszard; Synlett; nb. 7; (1998); p. 721 - 722 View in Reaxys

Rx-ID: 5267508 View in Reaxys 102/502 Yield

Conditions & References With water, silica gel in dichloromethane, Hydrolysis Haak, Edgar; Bytschkov, Igor; Doye, Sven; Angewandte Chemie - International Edition; vol. 38; nb. 22; (1999); p. 3389 - 3391 View in Reaxys With hydrogenchloride Khedkar, Vivek; Tillack, Annegret; Beller, Matthias; Organic Letters; vol. 5; nb. 25; (2003); p. 4767 - 4770 View in Reaxys 2H

Rx-ID: 9340808 View in Reaxys 103/502 Yield 6 mg

Conditions & References With silver tetrafluoroborate, di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium, deuterium, triphenylphosphine in dichloromethane, T= 20 °C Cross, Paul W. C.; Ellames, George J.; Gibson, Jennifer S.; Herbert, John M.; Kerr, William J.; McNeill, Alan H.; Mathers, Trevor W.; Tetrahedron; vol. 59; nb. 18; (2003); p. 3349 - 3358 View in Reaxys

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Rx-ID: 10074165 View in Reaxys 104/502 Yield

Conditions & References

85 %

With [bis(acetoxy)iodo]benzene, sulfuric acid in methanol, Time= 0.333333h, T= -20 °C Yusubov; Zholobova; Filimonova; Chi, Ki-Whan; Russian Chemical Bulletin; vol. 53; nb. 8; (2004); p. 1735 - 1742 View in Reaxys

Rx-ID: 10397331 View in Reaxys 105/502 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 N

Rx-ID: 11099975 View in Reaxys 106/502 Yield

Conditions & References

90 %

With sulfuric acid in tetrahydrofuran, Time= 10h, Heating Najera, Francisco; Garcia-Segura, Rafael; Perez-Inestrosa, Ezequiel; Sanchez-Sanchez, Cristobal; Suau, Rafael; Photochemistry and Photobiology; vol. 82; nb. 1; (2006); p. 248 - 253 View in Reaxys

O HO

Rx-ID: 11253389 View in Reaxys 107/502 Yield

Conditions & References

54 %, 5 %

With dicobalt octacarbonyl, Time= 24h, T= 20 °C , p= 760.051Torr Denmark, Scott E.; Ahmad, Moballigh; Journal of Organic Chemistry; vol. 72; nb. 25; (2007); p. 9630 - 9634 View in Reaxys

O O O

Rx-ID: 28211095 View in Reaxys 108/502 Yield 95 %Spectr.

Conditions & References With 5 Pd/C, 2-(trimethylsilyl)ethyl 4-(biphenyl-4-yl)-3-oxobutanoate, hydrogen, triethylamine in ethyl acetate, Time= 9h, T= 20 °C , p= 750.075Torr Knobloch, Eva; Brueckner, Reinhard; Synthesis; nb. 14 SPEC. ISS.; (2008); p. 2229 - 2246; Art.No: C02108SS View in Reaxys

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O O

Rx-ID: 29508993 View in Reaxys 109/502 Yield

Conditions & References

74 %

With copper(l) iodide, K3PO4*3H2O in dimethyl sulfoxide, Time= 20h, T= 110 °C , Inert atmosphere He, Chuan; Guo, Sheng; Huang, Li; Lei, Aiwen; Journal of the American Chemical Society; vol. 132; nb. 24; (2010); p. 8273 - 8275 View in Reaxys

HO H

Rx-ID: 38389798 View in Reaxys 110/502 Yield

Conditions & References With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in aq. buffer, T= 50 °C , pH= 8.9, Enzymatic reaction, Kinetics, Reagent/catalyst, enantiospecific reaction Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys 2.2.2. General procedure for mutant TeSADH-catalyzed racemization General procedure: Enantiopure alcohol (0.015 mmol), NADP+ (0.5 mg), NADPH (1.0 mg), mutant TeSADH (0.2 mg in Tris–HCl buffer solution, 50 mM, pH 8.0), Tris–HCl buffer solution (950 μL, 50 mM, pH 8.0), and acetonitrile (50 μL) were mixed in a 1.5-mL plastic tube. The reaction mixture was shaken at 50 °C and 200 rpm for 48 h, followed by extraction with ethyl acetate (2 × 500 μL). The combined organic layer was dried with sodium sulfate and concentrated to dryness. The remaining residue was treated with pyridine (two drops) and acetic anhydride (one drop) for 1 h to convert the alcohols to their corresponding acetates. The acetate products were diluted with CHCl3 prior to analysis on a GC equipped with a chiral column to determine ee. With NADPH, NADP+, W110G TeSADH in acetonitrile, T= 50 °C , pH= 8, Enzymatic reaction Musa, Musa M.; Patel, Jay M.; Nealon, Christopher M.; Kim, Chang Sup; Phillips, Robert S.; Karume, Ibrahim; Journal of Molecular Catalysis B: Enzymatic; vol. 115; (2015); p. 155 - 159 View in Reaxys

Rx-ID: 40649660 View in Reaxys 111/502 Yield

Conditions & References

53 %, 21 % Stage 1:Time= 0.05h, Inert atmosphere Stage 2: With tert.-butylhydroperoxide, Time= 1h, T= 102 °C , Inert atmosphere Fraile, Jos M.; Garca, Nuria; Mayoral, Jos A.; Santomauro, Fabio G.; Guidotti, Matteo; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3552 - 3561 View in Reaxys

Rx-ID: 1730128 View in Reaxys 112/502

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Yield

Conditions & References

30 % Chro- With tri-n-butyltin methoxide, bis (triortho-tolylphosphine)palladium(II) chloride in toluene, Time= 5h, T= 100 °C mat. Kosugi, Masanori; Hagiwara, Isao; Sumiya, Takao; Migita, Toshihiko; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 241 - 246 View in Reaxys

–O

O O

Na +

Rx-ID: 1839900 View in Reaxys 113/502 Yield

O O

S O S

Rx-ID: 2831631 View in Reaxys 114/502 Yield

Conditions & References

86 %

With hydrogenchloride in methanol, Time= 2h, Heating Ogura, Katsuyuki; Suzuki, Michiyo; Watanabe, Jun-ichi; Yamashita, Mitsuo; Iida, Hirotada; Tsuchihashi, Genichi; Chemistry Letters; (1982); p. 813 - 814 View in Reaxys

O Cl

Rx-ID: 3346426 View in Reaxys 115/502 Yield

Conditions & References

54 %

With (bpy)NiBr2, tetra-n-butylammonium tetrafluoroborate, Ambient temperature, Al rod/nickel-sponge, electrolysis Durandetti; Sibille; Nedelec; Perichon; Synthetic Communications; vol. 24; nb. 2; (1994); p. 145 - 151 View in Reaxys

54 %

With (bpy)NiBr2, tetra-n-butylammonium tetrafluoroborate in N,N-dimethyl-formamide, Ambient temperature, i = 250 mA, nickel-sponge cathode Durandetti, Muriel; Nedelec, Jean-Yves; Perichon, Jacques; Journal of Organic Chemistry; vol. 61; nb. 5; (1996); p. 1748 - 1755 View in Reaxys

O O O

I O

F F

Rx-ID: 25991608 View in Reaxys 116/502 Yield 93 %

Conditions & References Stage 1: in dichloromethane, Time= 0.25h Stage 2: With silica gel in dichloromethane, Further stages.

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Tellitu, Imanol; Dominguez, Esther; Tetrahedron; vol. 64; nb. 10; (2008); p. 2465 - 2470 View in Reaxys

(v5)

(v2)

(v5) Ni (v5)

(v5)

(v5) Ni

Br (v2)

(v5)

Rx-ID: 26628272 View in Reaxys 117/502 Yield

Conditions & References With C6H5I, H(1+), H2O in N,N-dimethyl-formamide, 25-60°C Hegedus, L. S.; Stiverson, R. K.; Journal of the American Chemical Society; vol. 96; (1974); p. O325 - O3254 View in Reaxys vol. Ni: Org.Verb.2; 2.3.1.7, page 305 - 310 ; (from Gmelin) View in Reaxys

CrO 3

Rx-ID: 28819264 View in Reaxys 118/502 Yield

Conditions & References

61 %

Stage 1: in dichloromethane, T= 20 °C , Inert atmosphere Stage 2: in dichloromethane, T= 20 °C , Inert atmosphere Balamurugan, Rengarajan; Gudla, Vanajakshi; Organic Letters; vol. 11; nb. 14; (2009); p. 3116 - 3119 View in Reaxys

S N

Rx-ID: 28874575 View in Reaxys 119/502 Yield

Conditions & References With AuBr3, water, sodium hydroxide, isopentyl nitrite in tetrahydrofuran, Time= 12h, T= 20 °C , pH= 7 Bures, Jordi; Lsart, Carles; Vllarrasa, Jaume; Organic Letters; vol. 11; nb. 19; (2009); p. 4414 - 4417 View in Reaxys

O transtrans trans

trans

Rx-ID: 29985026 View in Reaxys 120/502 Yield

Conditions & References

41.9 %, 11.3 %, 40 %

With C34H35N3O2 (2-)*Cl(1-)*Fe(3+), dihydrogen peroxide in acetonitrile, Time= 4h, T= 20 °C , Inert atmosphere Bilis; Christoforidis; Deligiannakis; Louloudi; Catalysis Today; vol. 157; nb. 1-4; (2010); p. 101 - 106 View in Reaxys

Rx-ID: 41758402 View in Reaxys 121/502 Yield 50 %

Conditions & References in tetrahydrofuran, T= 0 - 20 °C

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Ge, Jing-Jie; Yao, Chuan-Zhi; Wang, Mei-Mei; Zheng, Hong-Xing; Kang, Yan-Biao; Li, Yadong; Organic Letters; vol. 18; nb. 2; (2016); p. 228 - 231 View in Reaxys

HO O

Rx-ID: 66211 View in Reaxys 122/502 Yield

Conditions & References

27 %

With sodium acetate, acetic anhydride, Time= 6.5h, T= 160 °C Ammermann, Sven; Hrib, Christian; Jones, Peter G.; Du Mont, Wolf-Walther; Kowalsky, Wolfgang; Johannes, Hans-Hermann; Organic Letters; vol. 14; nb. 19; (2012); p. 5090 - 5093 View in Reaxys With diethyl ether, methyllithium Tegner; Acta Chemica Scandinavica (1947-1973); vol. 6; (1952); p. 782,788 View in Reaxys With acetic acid, T= 390 - 400 °C , beim Leiten ueber ThO2 Pickard; Kenyon; Journal of the Chemical Society; vol. 105; (1914); p. 1124 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. 1337; Bulletin de la Societe Chimique de France; vol. <4> 7; (1910); p. 654 View in Reaxys

HO N

O N O

Rx-ID: 1553479 View in Reaxys 123/502 Yield

Conditions & References

35 %, 6 %, With titanium(III) chloride in tetrahydrofuran, water, Time= 0.5h, T= 0 °C , pH 6.5 7% Sera, Akira; Fukumoto, Shoji; Tamura, Masako; Takabatake, Kiyoshi; Yamada, Hiroaki; Itoh, Kuniaki; Bulletin of the Chemical Society of Japan; vol. 64; nb. 6; (1991); p. 1787 - 1791 View in Reaxys O N O

Rx-ID: 1986971 View in Reaxys 124/502 Yield 6 %, 43 %

Conditions & References With sulfuric acid, toluene-4-sulfonic acid in methanol, T= 0 - 5 °C , ceramic diaphragm, carbon-rod anode, platinum cathode, 4.5 F/mol, 0.1A, cathode potential -1.45 to -1.65V vs. SCE Shono, Tatsuya; Hamaguchi, Hiroshi; Mikami, Hiroshi; Nogusa, Hideo; Kashimura, Shigenori; Journal of Organic Chemistry; vol. 48; nb. 12; (1983); p. 2103 - 2105 View in Reaxys

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O S O

Rx-ID: 2135631 View in Reaxys 125/502 Yield

Conditions & References

67 %

With aluminium amalgam in tetrahydrofuran, water, Heating Barre, V.; Massias, F.; Uguen, D.; Tetrahedron Letters; vol. 30; nb. 52; (1989); p. 7389 - 7392 View in Reaxys

N N H

Rx-ID: 2820973 View in Reaxys 126/502 Yield

Conditions & References

69 %

With water, oxalic acid in diethyl ether, Time= 18h Baldwin, Jack E.; Adlington, Robert M.; Bottaro, Jeffrey C.; Kolhe, Jayant N.; Perry, Matthew W. D.; Jain, Ashok U.; Tetrahedron; vol. 42; nb. 15; (1986); p. 4223 - 4234 View in Reaxys

Rx-ID: 3523153 View in Reaxys 127/502 Yield

Conditions & References With potassium tert-butylate, iron(II) chloride, 1.) DMSO, 25 deg C, 2.) DMSO, 25 deg C, 4 min, Yield given. Multistep reaction Galli, Carlo; Bunnett, J. F.; Journal of Organic Chemistry; vol. 49; nb. 16; (1984); p. 3041 - 3042 View in Reaxys

50 % Chro- With potassium tert-butylate in dimethyl sulfoxide, Time= 1h, T= 25 °C mat. Scamehorn, Richard G.; Hardacre, Jerry M.; Lukanich, Jeanne M.; Sharpe, Lee R.; Journal of Organic Chemistry; vol. 49; nb. 25; (1984); p. 4881 - 4883 View in Reaxys

O O

Rx-ID: 5084790 View in Reaxys 128/502 Yield 74 %

Conditions & References With PEG-400, sulfuric acid in water, Reflux Rao, H. Surya Prakash; Padmavathy; Vasantham; Rafi, Shaik; Synthetic Communications; vol. 39; nb. 10; (2009); p. 1825 - 1834 View in Reaxys

59 %

With bis(cyclopentadienyl)titanium dichloride, iso-propylmagnesium 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

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Cp2TiC5H20

Rx-ID: 6046456 View in Reaxys 129/502 Yield

Conditions & References

97 % Chro- With hydrogenchloride in toluene, 1.) 0 deg C, 5 min, then 3 deg C, 45 min, 2.) -10 deg C mat. Stille,J.R.; Grubbs,R.H.; Journal of the American Chemical Society; vol. 105; (1983); p. 1664 View in Reaxys

O Mg

etheric solution of acetic acid anhydride

Rx-ID: 6046457 View in Reaxys 130/502 Yield

Conditions & References With diethyl ether, T= -70 °C Newman; Booth; Journal of the American Chemical Society; vol. 67; (1945); p. 154 View in Reaxys

Rx-ID: 10551435 View in Reaxys 131/502 Yield 87 %

Conditions & References With 1-n-butylpyridinium tetrachloroferrate, pyridinium chlorochromate, Time= 0.466667h, T= 50 °C Khosropour, Ahmad R.; Khodaei, Mohammad M.; Ghaderi, Sattar; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 3; (2006); p. 326 - 330 View in Reaxys

O O

Rx-ID: 10553585 View in Reaxys 132/502 Yield 92 %

Conditions & References With 1-n-butylpyridinium tetrachloroferrate, pyridinium chlorochromate, Time= 0.583333h, T= 50 °C Khosropour, Ahmad R.; Khodaei, Mohammad M.; Ghaderi, Sattar; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 3; (2006); p. 326 - 330 View in Reaxys

HO H

Rx-ID: 34106261 View in Reaxys 133/502 Yield 52 %

Conditions & References With Arthrobacter atrocyaneus in N,N-dimethyl-formamide, Time= 72h, 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

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View in Reaxys

H 2N

Mg Cl

Rx-ID: 817890 View in Reaxys 134/502 Yield

Conditions & References With diethyl ether, T= 0 °C Whitmore; Sloat; Journal of the American Chemical Society; vol. 64; (1942); p. 2968 View in Reaxys

O Si E

O S

O O Si

Rx-ID: 1763874 View in Reaxys 135/502 Yield

Conditions & References

97 %

With cyclohexanone in dichloromethane, Time= 3h, T= -32 °C Camporeale, Michele; Fiorani, Tiziana; Troisi, Luigino; Adam, Waldemar; Curci, Ruggero; Edwards, John O.; Journal of Organic Chemistry; vol. 55; nb. 1; (1990); p. 93 - 98 View in Reaxys

97 %

With cyclohexanone, Time= 3h, T= -32 °C , Quantum yield Camporeale, Michele; Fiorani, Tiziana; Troisi, Luigino; Adam, Waldemar; Curci, Ruggero; Edwards, John O.; Journal of Organic Chemistry; vol. 55; nb. 1; (1990); p. 93 - 98 View in Reaxys

O O

Rx-ID: 2068297 View in Reaxys 136/502 Yield

Conditions & References

10 %

With oxygen, copper in acetonitrile, Time= 15h, T= 50 °C Toussaint, Olivier; Capdevielle, Patrice; Maumy, Michel; Tetrahedron Letters; vol. 25; nb. 35; (1984); p. 3819 3822 View in Reaxys

O O

Rx-ID: 2295039 View in Reaxys 137/502 Yield 15 % Spectr.

Conditions & References With diiodo monosilane in chloroform-d1, Time= 0.166667h, T= -42 °C , other reagent: iodotrimethylsilane (TMSI) Keinan, E.; Perez, D.; Sahai, M.; Shvily, R.; Journal of Organic Chemistry; vol. 55; nb. 9; (1990); p. 2927 - 2938 View in Reaxys

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Cl O

Rx-ID: 2536063 View in Reaxys 138/502 Yield

Conditions & References

89 %

With sulfuryl dichloride in dichloromethane, 1.) 0 deg C, 2.) room temperature, Yields of byproduct given Benneche, Tore; Christiansen, Mette L.; Undheim, Kjell; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 40; nb. 8; (1986); p. 700 - 702 View in Reaxys

Br O

Rx-ID: 2536064 View in Reaxys 139/502 Yield

Conditions & References

91 %

With bromine in tetrachloromethane, 1.) -20 deg C, 2.) room temperature, Yields of byproduct given Benneche, Tore; Christiansen, Mette L.; Undheim, Kjell; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 40; nb. 8; (1986); p. 700 - 702 View in Reaxys

Z K+

O–

H C– CH –2

Rx-ID: 2615607 View in Reaxys 140/502 Yield

Conditions & References With n-butyllithium in tetrahydrofuran, hexane, Time= 0.333333h, T= 0 - 5 °C Trimitsis, G. B.; Hinkley, J. M.; TenBrink, R.; Faburada, A. L.; Anderson, R.; et al.; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 2957 - 2962 View in Reaxys

O Cl

Rx-ID: 2694817 View in Reaxys 141/502 Yield

Conditions & References

30 %, 15 % With tetra-(n-butyl)ammonium iodide in N,N-dimethyl-formamide, T= 0 - 10 °C , electrolysis d'Incan, Esther; Sibille, Soline; Perichon, Jacques; Moingeon, Marie-Odile; Chaussard, Jacques; Tetrahedron Letters; vol. 27; nb. 35; (1986); p. 4175 - 4176 View in Reaxys

O O racemate

Rx-ID: 4795377 View in Reaxys 142/502 Yield 56 %

Conditions & References T= 650 °C , p= 0.01Torr Aitken, R. Alan; Thomas, Andrew W.; Synlett; nb. 1; (1998); p. 102 - 104 View in Reaxys

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O E

Rx-ID: 5093153 View in Reaxys 143/502 Yield

Conditions & References

21.7 % Chromat., 19.3 % Chromat., 34 % Chromat., 6.2 % Chromat.

With water, RuCl2(C6H6)(PPh2(C6F5)), Time= 12h, Further byproducts given. Title compound not separated from by-

6.2 % Chromat., 19.3 % Chromat., 34 % Chromat., 21.7 % Chromat.

With water, RuCl2(C6H6)(PPh2(C6F5)), Time= 12h, Further byproducts given. Title compound not separated from by-

products Tokunaga, Makoto; Wakatsuki, Yasuo; Angewandte Chemie - International Edition; vol. 37; nb. 20; (1998); p. 2867 - 2869 View in Reaxys

With water, lt;RuCl2(C6H6)gt;lt;PPh2(C6F5)gt;, diphenyl(pentafluorophenyl)phosphine in isopropyl alcohol, Time= 12h, T= 70 °C , another catalyst, temperatures, time and solvent, Product distribution Tokunaga, Makoto; Wakatsuki, Yasuo; Angewandte Chemie - International Edition; vol. 37; nb. 20; (1998); p. 2867 - 2869 View in Reaxys

O O

Rx-ID: 5100897 View in Reaxys 144/502 Yield

Conditions & References

58 %

64 %Spectr.

With 2-(trimethylsilyl)ethyl 4-(biphenyl-4-yl)-3-oxobutanoate, caesium carbonate, thiophenol in N,N-dimethyl-formamide, Time= 3.5h, T= 85 °C Knobloch, Eva; Brueckner, Reinhard; Synthesis; nb. 14 SPEC. ISS.; (2008); p. 2229 - 2246; Art.No: C02108SS View in Reaxys

O N O

O E

Rx-ID: 9178685 View in Reaxys 145/502 Yield

Conditions & References With tris(triphenylphosphine)ruthenium(II) chloride, hydrogen in dichloromethane, Time= 24h, p= 14710.2Torr , Heating Li, Yanjun; Izumi, Taeko; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 49; nb. 4; (2002); p. 505 508 View in Reaxys With glycerol trinitrate reductase from Agrobacterium radiobacter, Reduced nicotinamide-adenine dinucleotide in dimethyl sulfoxide, Time= 24h, T= 30 °C , pH= 7.5, aq. buffer, Enzymatic reaction

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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 N

OH N

Si O

racemate

Rx-ID: 10068906 View in Reaxys 146/502 Yield 17 %

Conditions & References With boron trifluoride diethyl etherate in dichloromethane, Time= 1h, T= -50 °C De Los Rios, Cristobal; Hegedus, Louis S.; Journal of Organic Chemistry; vol. 70; nb. 16; (2005); p. 6541 - 6543 View in Reaxys

O cis cis

cis cis

Rx-ID: 10198848 View in Reaxys 147/502 Yield

Conditions & References With dihydrogen peroxide, [γ-1,2-H2SiV2W10O40] immobilized on surface-modified SiO2 in acetonitrile, tert-butyl alcohol, Time= 24h, T= 19.85 °C Kasai, Jun; Nakagawa, Yoshinao; Uchida, Sayaka; Yamaguchi, Kazuya; Mizuno, Noritaka; Chemistry - A European Journal; vol. 12; nb. 15; (2006); p. 4176 - 4184 View in Reaxys

HO B HO

Rx-ID: 11573536 View in Reaxys 148/502 Yield

Conditions & References Reaction Steps: 3 1: 97 percent / [rhodium(OH)(1,5-cyclooctadiene)]2 / dioxane; H2O / 3 h / 25 °C 2: 80 percent / lithium diisopropylamide / 1 h / -78 °C 3: 87 percent / sulfuric acid / toluene / 1 h / 100 °C With sulfuric acid, lithium diisopropyl amide, [rhodium(OH)(1,5-cyclooctadiene)]2 in 1,4-dioxane, water, toluene Yoshida, Suguru; Yorimitsu, Hideki; Oshima, Koichiro; Synlett; nb. 10; (2007); p. 1622 - 1624 View in Reaxys Reaction Steps: 3 1.1: trifluoroacetic acid / 0.25 h / 20 °C / Inert atmosphere 2.1: potassium fluoride / ethylene glycol dimethyl ether / 18 h / 20 °C / Inert atmosphere 3.1: chloro-trimethyl-silane / ethylene glycol dimethyl ether / 0.33 h / -20 - -10 °C / Inert atmosphere 3.2: 3 h / -20 - 20 °C / Inert atmosphere With potassium fluoride, chloro-trimethyl-silane, trifluoroacetic acid in ethylene glycol dimethyl ether Elkin, Pavel K.; Levin, Vitalij V.; Dilman, Alexander D.; Struchkova, Marina I.; Belyakov, Pavel A.; Arkhipov, Dmitry E.; Korlyukov, Alexander A.; Tartakovsky, Vladimir A.; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5259 - 5263

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View in Reaxys

Rx-ID: 35535061 View in Reaxys 149/502 Yield 73 %

Conditions & References With [Pd(η3-1-Ph-allyl)(μ-Cl)]2, 2-methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine, caesium carbonate, Time= 12h, T= 90 °C , Inert atmosphere, Schlenk technique, Sealed tube Li, Pengbin; Lue, Bo; Fu, Chunling; Ma, Shengming; Advanced Synthesis and Catalysis; vol. 355; nb. 7; (2013); p. 1255 - 1259 View in Reaxys

64 %Chromat.

With C38H49N2P*C9H10ClPd, caesium carbonate, sodium t-butanolate in ethylene glycol dimethyl ether, Time= 1.25h, T= 90 °C , Inert atmosphere, Schlenk technique Wheaton, Craig A.; Bow, John-Paul J.; Stradiotto, Mark; Organometallics; vol. 32; nb. 21; (2013); p. 6148 - 6161 View in Reaxys

Rx-ID: 306776 View in Reaxys 150/502 Yield

Conditions & References With sulfuric acid, T= -19 °C Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys With sulfuric acid, T= 50 - 55 °C Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys With sulfuric acid Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 142; (1906); p. 1538; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 351 View in Reaxys With sulfuric acid, water Sunagawa; Okuda; Yakugaku Zasshi; vol. 72; (1952); p. 117; ; (1952); p. 11146 View in Reaxys Hirao; Kogyo Kagaku Zasshi; vol. 56; (1953); p. 265; ; (1954); p. 10534 View in Reaxys With sulfuric acid Levy; Gombinska; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 713 View in Reaxys Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 142; (1906); p. 1538; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 351 View in Reaxys Zincke; Zahn; Chemische Berichte; vol. 43; (1910); p. 855 View in Reaxys

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O N O

Rx-ID: 1553478 View in Reaxys 151/502 Yield

Conditions & References

32 %, 60 % With titanium(III) chloride in tetrahydrofuran, water, Time= 24h, T= 35 °C , pH 6.5 Sera, Akira; Fukumoto, Shoji; Tamura, Masako; Takabatake, Kiyoshi; Yamada, Hiroaki; Itoh, Kuniaki; Bulletin of the Chemical Society of Japan; vol. 64; nb. 6; (1991); p. 1787 - 1791 View in Reaxys 32 %, 60 % With titanium(III) chloride, ammonium acetate in tetrahydrofuran, water, Time= 24h, T= 35 °C Sera, Akira; Fukumoto, Shoji; Yoneda, Takako; Yamada, Hiroaki; Heterocycles; vol. 24; nb. 3; (1986); p. 697 - 702 View in Reaxys 60 %, 32 % With titanium(III) chloride in n-heptane, Time= 24h, T= 35 °C , other 1-nitro-2-phenylethenes Sera, Akira; Fukumoto, Shoji; Tamura, Masako; Takabatake, Kiyoshi; Yamada, Hiroaki; Itoh, Kuniaki; Bulletin of the Chemical Society of Japan; vol. 64; nb. 6; (1991); p. 1787 - 1791 View in Reaxys 60 %, 32 % With titanium(III) chloride, ammonium acetate in tetrahydrofuran, water, Time= 24h, T= 35 °C Sera, Akira; Fukumoto, Shoji; Yoneda, Takako; Yamada, Hiroaki; Heterocycles; vol. 24; nb. 3; (1986); p. 697 - 702 View in Reaxys 60 %, 32 % With titanium(III) chloride in tetrahydrofuran, water, Time= 24h, T= 35 °C , pH 6.5 Sera, Akira; Fukumoto, Shoji; Tamura, Masako; Takabatake, Kiyoshi; Yamada, Hiroaki; Itoh, Kuniaki; Bulletin of the Chemical Society of Japan; vol. 64; nb. 6; (1991); p. 1787 - 1791 View in Reaxys

Rx-ID: 1564470 View in Reaxys 152/502 Yield

Conditions & References

82 % Chro- With samarium diiodide, tert-butyl alcohol in tetrahydrofuran, Time= 24h, Ambient temperature, Title compound not mat. separated from byproducts Girard, P.; Namy, J. L.; Kagan, H. B.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2693 2698 View in Reaxys

O– F

K+

Rx-ID: 1710103 View in Reaxys 153/502 Yield 42 % Chromat., 29 % Chromat., 12 % Chromat.

Conditions & References With ammonia, T= -33 °C Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

12 % Chro- With ammonia, T= -33 °C mat., 29 % Chromat.,

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42 % Chro- Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical mat. Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

O– K+

Rx-ID: 1710685 View in Reaxys 154/502 Yield

Conditions & References

11 % Chromat., 6 % Chromat., 78 % Chromat.

With ammonia, T= -33 °C

78 % Chromat., 6 % Chromat., 11 % Chromat.

With ammonia, T= -33 °C

Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

O– K+

Rx-ID: 1769111 View in Reaxys 155/502 Yield

Conditions & References

28 % Chromat., 41 % Chromat., 7 % Chromat.

With ammonia, T= -33 °C

7 % Chromat., 41 % Chromat., 28 % Chromat.

With ammonia, T= -33 °C

Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

O– K+

Rx-ID: 2017552 View in Reaxys 156/502 Yield

Conditions & References

34 % Chromat., 17 % Chromat., 30 % Chromat.

With ammonia, T= -33 °C

30 % Chromat., 17 % Chromat., 34 % Chromat.

With ammonia, T= -33 °C

Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

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O– N+

K+

I–

Rx-ID: 2303947 View in Reaxys 157/502 Yield

Conditions & References

20 % Chromat., 12 % Chromat., 54 % Chromat.

With ammonia, T= -33 °C

54 % Chromat., 12 % Chromat., 20 % Chromat.

With ammonia, T= -33 °C

Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

Rx-ID: 2879607 View in Reaxys 158/502 Yield

Conditions & References

25 %, 75 % 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 Bio-Organic Chemistry (1972-1999); (1980); p. 1098 - 1103 View in Reaxys 75 %, 25 % 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 Bio-Organic Chemistry (1972-1999); (1980); p. 1098 - 1103 View in Reaxys

O– K+

Rx-ID: 3377385 View in Reaxys 159/502 Yield

Conditions & References

37 % Chromat., 18 % Chromat., 20 % Chromat.

With ammonia, T= -33 °C

20 % Chromat., 18 % Chromat., 37 % Chromat.

With ammonia, T= -33 °C

Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

2-nitro-1-phenyl-propene-(1) Rx-ID: 6046448 View in Reaxys 160/502 Yield

Conditions & References With palladium on activated charcoal, water, T= 28 - 36 °C , p= 25742.8Torr , Hydrogenation.anschliessendes Erwaermen mit wss. NaOH auf 65grad und Behandeln des Reaktionsprodukts mit wss. H2SO4

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Patent; Comm. Solv. Corp.; US2427822; (1945) View in Reaxys With hydrogenchloride, iron(III) chloride, iron Patent; Purdue Research Found.; US2233823; (1939) View in Reaxys

Rx-ID: 8863596 View in Reaxys 161/502 Yield

Conditions & References

77 %, 1 %

With dimethyl sulfoxide, palladium dichloride, Time= 12h, T= 90 °C Yusubov; Filimonov; Chi, Ki-Whan; Russian Chemical Bulletin; vol. 50; nb. 4; (2001); p. 649 - 653 View in Reaxys

Rx-ID: 9778030 View in Reaxys 162/502 Yield

Conditions & References

60 % Chro- With sodium hypochlorite, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, T= 20 °C , pH= 8.5 - 9 mat. 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

Rx-ID: 10118993 View in Reaxys 163/502 Yield 92 %

Conditions & References With trinitratocerium(IV) bromate, Time= 0.7h, Heating Shirini, Farhad; Esm-Hosseini, Majid; Hejazi, Zoha; Synthetic Communications; vol. 35; nb. 22; (2005); p. 2913 2919 View in Reaxys Reaction Steps: 2 1: 90 percent / tris[trinitratocerium(IV)] paraperiodate / 0.02 h / 20 °C 2: 90 percent / tris[trinitratocerium(IV)] paraperiodate / 0.33 h / 90 °C With tris[trinitratocerium(IV)] paraperiodate Shirini; Esm-Hosseini; Hejazi; Mohammadpoor-Baltork; Journal of Chemical Research; nb. 1; (2006); p. 29 - 31 View in Reaxys Reaction Steps: 2 1: 92 percent / trinitratocerium(IV) bromate / 0.08 h / 20 °C 2: 95 percent / trinitratocerium(IV) bromate / 0.8 h / Heating With trinitratocerium(IV) bromate Shirini, Farhad; Esm-Hosseini, Majid; Hejazi, Zoha; Synthetic Communications; vol. 35; nb. 22; (2005); p. 2913 2919 View in Reaxys

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Rx-ID: 18522224 View in Reaxys 164/502 Yield

Conditions & References Reaction Steps: 3 1: 90 percent / 2 h / 20 °C 2: trifluoroacetic acid / 6 h / 20 °C 3: (CO2H)2 / H2O; diethyl ether / 14 h With oxalic acid in diethyl ether, water, trifluoroacetic acid Adlington, Robert M.; Baldwin, Jack E.; Bottaro, Jeffrey C.; Perry, Matthew W. D.; Journal of the Chemical Society, Chemical Communications; nb. 18; (1983); p. 1040 - 1041 View in Reaxys Reaction Steps: 3 1: 1.) n-butyl lithium / 1.) THF, 0 deg C, 10 min; -78 deg C, 2.) THF, -78 to 25 deg C, 3 h; 25 deg C, 18 h 2: TFA / CH2Cl2 / 18 h / 25 °C 3: 69 percent / oxalic acid, water / diethyl ether / 18 h With n-butyllithium, water, oxalic acid, trifluoroacetic acid in diethyl ether, dichloromethane Baldwin, Jack E.; Adlington, Robert M.; Bottaro, Jeffrey C.; Kolhe, Jayant N.; Perry, Matthew W. D.; Jain, Ashok U.; Tetrahedron; vol. 42; nb. 15; (1986); p. 4223 - 4234 View in Reaxys Reaction Steps: 2 1: 77 percent / 1.3 eq. NaH / dimethylformamide / 1.) 0 deg C, 20 min., 2.) room temp., 16 h. 2: 86 percent / conc. hydrochloric acid / methanol / 2 h / Heating With hydrogenchloride, sodium hydride in methanol, N,N-dimethyl-formamide Ogura, Katsuyuki; Suzuki, Michiyo; Watanabe, Jun-ichi; Yamashita, Mitsuo; Iida, Hirotada; Tsuchihashi, Genichi; Chemistry Letters; (1982); p. 813 - 814 View in Reaxys Reaction Steps: 2 1: NaH / dimethylformamide / 1.) room temperature, 48h, 2.) 60 deg C, 3h 2: different reagents and reaction times / methanol / Heating With sodium hydride in methanol, N,N-dimethyl-formamide Ogura, Katsuyuki; Ohtsuki, Kazuo; Nakamura, Masami; Yahata, Nobuhiro; Takahashi, Kazumasa; Iida, Hirotada; Tetrahedron Letters; vol. 26; nb. 20; (1985); p. 2455 - 2458 View in Reaxys

O N

H O

N NH 2

O H

S O

O O N

O O

NH 2

O O

N N

Rx-ID: 25279442 View in Reaxys 165/502 Yield 580 mg (87%)

Conditions & References 19 : 1-phenyl-4-ethoxycarbonyl-5-(2,3,4,5,6-penta-O-acetyl-D-gluconylthioureido) pyrazole EXAMPLE 19 1-phenyl-4-ethoxycarbonyl-5-(2,3,4,5,6-penta-O-acetyl-D-gluconylthioureido) pyrazole To 10 ml of anhydrous benzene were added 450 mg (1 mmol) of 2,3,4,5,6-penta-O-acetyl-D-gluconyl isothiocyanate and 230 mg (1 mmol) of ethyl 1-phenyl-5-aminopyrazol-4-carboxylate and the mixture was refluxed on a water bath for 10 hours, after which the solvent was distilled off under a reduced pressure.

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The residue was purified by column chromatography on silica gel using benzene-acetone as eluent to give the titled compound from the fraction of benzene-acetone (9:1). Yield: 580 mg (87percent). IRνmax KBr cm- 1: 3400 (--NH), 1740, 1700 (COOCH3), 1590, 750 (phenyl). Elementary analysis: C28 H34 O13 N4 S requires: C, 50.45; H, 5.14; N, 8.40percent. Found: C, 50.40; H, 5.42; N, 8.62percent. in benzene Patent; Ogura; Haruo; US4025622; (1977); (A1) English View in Reaxys

H 2N

Rx-ID: 29118585 View in Reaxys 166/502 Yield

Conditions & References Stage 1: With AuNTf2(SPhos) 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 13C

13C

O N

BrLi

Rx-ID: 36130963 View in Reaxys 167/502 Yield

Conditions & References

84 %

in tetrahydrofuran, diethyl ether, Time= 6h, T= -78 - 0 °C , Inert atmosphere Cohen, Meital; Bretler, Uriel; Albeck, Amnon; Protein Science; vol. 22; nb. 6; (2013); p. 788 - 799 View in Reaxys

O E O

Rx-ID: 40649661 View in Reaxys 168/502 Yield

Conditions & References

13 %, 87 % Stage 1:Time= 0.05h, Inert atmosphere Stage 2: With tert.-butylhydroperoxide, Time= 1h, T= 102 °C , Inert atmosphere Fraile, Jos M.; Garca, Nuria; Mayoral, Jos A.; Santomauro, Fabio G.; Guidotti, Matteo; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3552 - 3561 View in Reaxys O

O O OH

Rx-ID: 40937634 View in Reaxys 169/502 Yield 9 %Chromat., 51%Chromat.

Conditions & References With water, oxygen, palladium diacetate in N,N-dimethyl acetamide, Time= 24h, T= 90 °C , p= 760.051Torr , Schlenk technique Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Li, Chunsheng; Wu, Wanqing; Jiang, Huanfeng; Chemical Communications; vol. 51; nb. 46; (2015); p. 9575 - 9578 View in Reaxys

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O O OH

Rx-ID: 40937636 View in Reaxys 170/502 Yield

Conditions & References

10 %Chro- With water, oxygen, palladium diacetate in 1,4-dioxane, Time= 24h, T= 100 °C , p= 760.051Torr , Schlenk technique mat., 7 %Chromat. Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Li, Chunsheng; Wu, Wanqing; Jiang, Huanfeng; Chemical Communications; vol. 51; nb. 46; (2015); p. 9575 - 9578 View in Reaxys

racemate

Rx-ID: 1764008 View in Reaxys 171/502 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

H O

Rx-ID: 1983187 View in Reaxys 172/502 Yield

Conditions & References With (NH4)2S2O8, 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 (NH4)2S2O8, copper diacetate, sodium acetate in acetonitrile, T= 100 °C , Yield given Walling, Cheves; El-Taliawi, Gamil M.; Zhao, Chengxue; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4914 - 4917 View in Reaxys 2H

2H 2H

O–

K+ 2H

2H 2H

Rx-ID: 1988730 View in Reaxys 173/502 Yield

Conditions & References With ammonia, T= -33 °C , Yield given. Title compound not separated from byproducts Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

Z racemate

racemate

Rx-ID: 2005276 View in Reaxys 174/502

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Yield

Rx-ID: 2962566 View in Reaxys 175/502 Yield

Conditions & References

100 %

With 2,2'-bipyridylchromium peroxide in benzene, Time= 1h, 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

100 %

With 2,2'-bipyridylchromium peroxide in benzene, Time= 1h, Heating Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Tetrahedron; vol. 42; nb. 2; (1986); p. 719 - 726 View in Reaxys

95 %

With tris[trinitratocerium(IV)] paraperiodate, Time= 0.166667h, T= 90 °C Shirini; Esm-Hosseini; Hejazi; Mohammadpoor-Baltork; Journal of Chemical Research; nb. 1; (2006); p. 29 - 31 View in Reaxys

98 % Chro- With sodium hypophosphite, nickel in ethanol, Time= 3h, T= 50 °C , pH 5 mat. Monti, D.; Gramatica, P.; Speranza, G.; Tagliapietra, S.; Manitto, P.; Synthetic Communications; vol. 16; nb. 7; (1986); p. 803 - 808 View in Reaxys

O O

Rx-ID: 3821287 View in Reaxys 176/502 Yield

Conditions & References

1 % Chromat., 3 % Chromat., 89 % Chromat.

With boron trifluoride diethyl etherate, Time= 1h, T= -78 °C , further reagents (chromyl nitrate, HNO3, ZnCl2), 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

O E O

Rx-ID: 20899559 View in Reaxys 177/502 Yield

Conditions & References Reaction Steps: 2 1: 85 percent / 30 percent H2O2 / bis(2-nitrophenyl) diselenide / CH2Cl2 / 128 h / Ambient temperature; further. reag. and cat.; var. time 2: 88 percent / cc. HCl / tetrahydrofuran; H2O / 7 h / Ambient temperature With hydrogenchloride, dihydrogen peroxide, O,O'-dinitrodiphenyl diselenide in tetrahydrofuran, dichloromethane, water Syper, Ludwik; Tetrahedron; vol. 43; nb. 12; (1987); p. 2853 - 2872

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View in Reaxys

Rx-ID: 21532118 View in Reaxys 178/502 Yield

Conditions & References Reaction Steps: 3 1: 98 percent / sodium methoxide / Ambient temperature 2: 89 percent / 1N aq. HCl / tetrahydrofuran 3: 67 percent / aluminium amalgam / tetrahydrofuran; H2O / Heating With hydrogenchloride, aluminium amalgam, sodium methylate in tetrahydrofuran, water Barre, V.; Massias, F.; Uguen, D.; Tetrahedron Letters; vol. 30; nb. 52; (1989); p. 7389 - 7392 View in Reaxys

Rx-ID: 27963888 View in Reaxys 179/502 Yield

Conditions & References Stage 1: With sodium hydroxide in toluene, Time= 1h Stage 2: With hydrogenchloride in toluene, Time= 5h, T= 60 - 95 °C , pH= 2.5, Further stages. Zimbron, Jeremy Malcolm; Seeger-Weibel, Manuela; Hirt, Hans; Gallou, Fabrice; Synthesis; nb. 8; (2008); p. 1221 - 1226 View in Reaxys

O O

Rx-ID: 28211108 View in Reaxys 180/502 Yield

Conditions & References

100 %Spectr.

With 2-(trimethylsilyl)ethyl 4-(biphenyl-4-yl)-3-oxobutanoate, palladium diacetate, triethylammonium formate, triphenylphosphine in tetrahydrofuran, Time= 2.5h, T= 20 °C Knobloch, Eva; Brueckner, Reinhard; Synthesis; nb. 14 SPEC. ISS.; (2008); p. 2229 - 2246; Art.No: C02108SS View in Reaxys

Rx-ID: 32365096 View in Reaxys 181/502 Yield

Conditions & References

10 %Chro- With tert.-butylhydroperoxide, .mu.-oxo-bis[dioxo-[(3'S,4'S)-2-(3',4'-dihydro-3'-phenyl-4'-methyloxy-methyl-2'-oxazolmat., 6 yl)pyridine-.kappa.2-N,N](isothiocyanato)molybdenum(VI)] in decane, dichloromethane, Time= 22h, T= 30 °C , Ionic %Chromat. liquid, Inert atmosphere Brito, Jose A.; Ladeira, Sonia; Teuma, Emmanuelle; Royo, Beatriz; Gomez, Montserrat; Applied Catalysis A: General; vol. 398; nb. 1-2; (2011); p. 88 - 95 View in Reaxys

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O O

Rx-ID: 40937635 View in Reaxys 182/502 Yield

Conditions & References

6 %Chromat., 18 %Chromat., 7 %Chromat.

With water, oxygen, palladium dichloride in N,N-dimethyl acetamide, Time= 24h, T= 100 °C , p= 760.051Torr , Schlenk technique Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Li, Chunsheng; Wu, Wanqing; Jiang, Huanfeng; Chemical Communications; vol. 51; nb. 46; (2015); p. 9575 - 9578 View in Reaxys

O O

Rx-ID: 283846 View in Reaxys 183/502 Yield

Conditions & References Hermanns; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 85; (1913); p. 234 View in Reaxys

66 mg

in water, T= 230 °C Dave, Vinod; Warnhoff, E. W.; Journal of Organic Chemistry; vol. 48; nb. 15; (1983); p. 2590 - 2598 View in Reaxys

O Br

Rx-ID: 743324 View in Reaxys 184/502 Yield

Conditions & References With sodium amide, in fluessigem NH3 Leake; Levine; Journal of the American Chemical Society; vol. 81; (1959); p. 1169,1171 View in Reaxys With bis (triortho-tolylphosphine)palladium(II) chloride, tri-n-butyltin methoxide, 2.) toluene, 100 deg C , 5 h, Yield given. Multistep reaction Kosugi, Masanori; Hagiwara, Isao; Sumiya, Takashi; Migita, Toshihiko; Journal of the Chemical Society, Chemical Communications; nb. 7; (1983); p. 344 - 345 View in Reaxys

Se N

O Se

Rx-ID: 1464114 View in Reaxys 185/502 Yield 60 %

Conditions & References With copper(I) benzeneselenide in diethyl ether Back, Thomas G.; Kerr, Russell G.; Tetrahedron; vol. 41; nb. 21; (1985); p. 4759 - 4764 View in Reaxys

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Se Se O

Rx-ID: 1470673 View in Reaxys 186/502 Yield

Conditions & References

60 %

With copper in diethyl ether Back, Thomas G.; Kerr, Russell G.; Tetrahedron; vol. 41; nb. 21; (1985); p. 4759 - 4764 View in Reaxys

O N O

Rx-ID: 1553470 View in Reaxys 187/502 Yield

Conditions & References

4 %, 85 %

With sodium dithionite, 1,1'-di-n-octyl-4,4'-bipyridinium dibromide in water, ethyl acetate, Time= 1h Tomioka, Hideo; Ueda, Koichi; Ohi, Hirofumi; Izawa, Yasuji; Chemistry Letters; (1986); p. 1359 - 1362 View in Reaxys

Rx-ID: 2965908 View in Reaxys 188/502 Yield

Conditions & References With hydrogenchloride in chloroform, Time= 1h, T= 50 °C Trapani, Giuseppe; Reho, Antonia; Latrofa, Andrea; Liso, Gaetano; Synthesis; nb. 1; (1988); p. 84 - 87 View in Reaxys

S N

H N O

Rx-ID: 2986321 View in Reaxys 189/502 Yield

Conditions & References With hydrogenchloride in chloroform, Time= 1h, T= 50 °C Trapani, Giuseppe; Reho, Antonia; Latrofa, Andrea; Liso, Gaetano; Synthesis; nb. 1; (1988); p. 84 - 87 View in Reaxys

(+-)-2-phenyl-propionaldehyde va‐ pour

Rx-ID: 6046446 View in Reaxys 190/502 Yield

Conditions & References With kieselguhr, T= 600 °C , p= 11032.6Torr

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Ramart-Lucas; Guerlain; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1860,1867 View in Reaxys

H P

Rx-ID: 9015086 View in Reaxys 191/502 Yield

Conditions & References Stage 1: With selenenyl bromide resin in tetrahydrofuran, Time= 0.5h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 2h, Heating, Wittig reaction Stage 3: With trifluoroacetic acid in dichloromethane, Time= 4h, T= 20 °C Huang, Xian; Sheng, Shou-Ri; Tetrahedron Letters; vol. 42; nb. 51; (2001); p. 9035 - 9037 View in Reaxys O

O Na + HO

P O–

Rx-ID: 10262416 View in Reaxys 192/502 Yield

Conditions & References in water-d2, acetonitrile, Time= 2h, 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

Rx-ID: 21274138 View in Reaxys 193/502 Yield

Conditions & References Reaction Steps: 2 1: 1.) trifluoromethanesulfonic acid (TFSA) / 1.) CH2Cl2, -40 deg C, 1 min, 2.) -78 deg C to 20 deg C 2: H2O, trifluoromethanesulfonic acid (TFSA) With trifluorormethanesulfonic acid, water Okabe, Kazuaki; Ohwada, Tomohiko; Ohta, Toshiharu; Shudo, Koichi; Journal of Organic Chemistry; vol. 54; nb. 4; (1989); p. 733 - 734 View in Reaxys Reaction Steps: 2 1: 88 percent / SnCl4 / 0.67 h / Ambient temperature 2: 94 percent / Zn dust, acetic acid / 1 h / 100 °C With acetic acid, zinc, tin(IV) chloride Tamura; Shindo; Uenishi; Ishibashi; Tetrahedron Letters; vol. 21; nb. 26; (1980); p. 2547 - 2548 View in Reaxys Reaction Steps: 2 1: 1) trifluoromethanesulfonic acid / 1) CH2Cl2, -40 deg C, 1 min, 2) -78 deg C up to r.t., 10-15 min 2: H2O / CH2Cl2 / Ambient temperature With trifluorormethanesulfonic acid, water in dichloromethane Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi; Tetrahedron; vol. 46; nb. 21; (1990); p. 7539 - 7555 View in Reaxys

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O racemate

Rx-ID: 29389171 View in Reaxys 194/502 Yield

Conditions & References With C12H6F18Fe3O16 in 1,2-dichloro-ethane, Time= 1h, T= 80 °C , Inert atmosphere, regioselective reaction Ertuerk, Erkan; Goellue, Mehmet; Demir, Ayhan S.; Tetrahedron; vol. 66; nb. 13; (2010); p. 2373 - 2377 View in Reaxys 2H

Rx-ID: 41758395 View in Reaxys 195/502 Yield

Conditions & References Reaction Steps: 3 1.1: sodium borodeuteride; iodine / tetrahydrofuran / 0 °C / |Reflux 2.1: thionyl chloride; triethylamine / dichloromethane / 15 - 20 °C 3.1: iodine; magnesium / tetrahydrofuran / 1 h / 25 °C 3.2: 0 - 20 °C With thionyl chloride, sodium borodeuteride, iodine, magnesium, triethylamine in tetrahydrofuran, dichloromethane Ge, Jing-Jie; Yao, Chuan-Zhi; Wang, Mei-Mei; Zheng, Hong-Xing; Kang, Yan-Biao; Li, Yadong; Organic Letters; vol. 18; nb. 2; (2016); p. 228 - 231 View in Reaxys 2H

Rx-ID: 41758397 View in Reaxys 196/502 Yield

Conditions & References Reaction Steps: 2 1.1: thionyl chloride; triethylamine / dichloromethane / 15 - 20 °C 2.1: iodine; magnesium / tetrahydrofuran / 1 h / 25 °C 2.2: 0 - 20 °C With thionyl chloride, iodine, magnesium, triethylamine in tetrahydrofuran, dichloromethane Ge, Jing-Jie; Yao, Chuan-Zhi; Wang, Mei-Mei; Zheng, Hong-Xing; Kang, Yan-Biao; Li, Yadong; Organic Letters; vol. 18; nb. 2; (2016); p. 228 - 231 View in Reaxys

O O

Rx-ID: 555334 View in Reaxys 197/502 Yield

Conditions & References With pyridine Smith; Journal of the American Chemical Society; vol. 75; (1953); p. 1134 View in Reaxys King; McMillan; Journal of the American Chemical Society; vol. 73; (1951); p. 4911,4914 View in Reaxys

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O O

Rx-ID: 797688 View in Reaxys 198/502 Yield

Conditions & References With diethyl ether, ethanol, magnesium diethoxide, anschliessend Kochen mit Phenylacetylchlorid und Kochen des Reaktionsprodukts mit wss. Essigsaeure und Schwefelsaeure Walker; Hauser; Journal of the American Chemical Society; vol. 68; (1946); p. 1386 View in Reaxys

O O

Rx-ID: 1616774 View in Reaxys 199/502 Yield

Conditions & References With tert.-butylhydroperoxide, tellurium (IV) oxide, silver(I) acetate, palladium dichloride in acetic acid, Time= 72h, Ambient temperature, Yield given. Yields of byproduct given Uemura, Sakae; Fukuzawa, Shin-ichi; Toshimitsu, Akio; Okano, Masaya; Tetrahedron Letters; vol. 23; (1982); p. 87 - 90 View in Reaxys

O O

H 2N

Rx-ID: 2141403 View in Reaxys 200/502 Yield

Conditions & References

26 %

With carbon monoxide, oxygen in dichloromethane Nishinaga, Akira; Yamazaki, Shigekazu; Matsuura, Teruo; Tetrahedron Letters; vol. 28; nb. 50; (1987); p. 6309 6312 View in Reaxys

Rx-ID: 3528265 View in Reaxys 201/502 Yield 83 %

Conditions & References With manganese triacetate in various solvent(s), Time= 1.5h, ultrasonic irradiation Yinghuai, Zhu; Bahnmueller, Stefan; Hosmane, Narayan S.; Maguire, John A.; Chemistry Letters; vol. 32; nb. 8; (2003); p. 730 - 731 View in Reaxys

40 %

With manganese triacetate, acetic acid, Time= 1.5h, Heating Kurz, Michael E.; Baru, Vijayalakshmi; Nguyen, P-Nhi; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1603 - 1607 View in Reaxys

39 % Chro- With manganese triacetate in acetic acid, Heating mat. Gardrat, C.; Bulletin des Societes Chimiques Belges; vol. 93; nb. 10; (1984); p. 897 - 902 View in Reaxys With manganese triacetate in acetic acid, T= 70 °C , Rate constant

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Vinogradova, M. G.; Min, R. S.; Aksenov, V. S.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; (1982); p. 1760 - 1765; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1982); p. 1994 - 1999 View in Reaxys

Rx-ID: 9215155 View in Reaxys 202/502 Yield

Conditions & References With hydrogenchloride Tillack, Annegret; Garcia Castro, Ivette; Hartung, Christian G.; Beller, Matthias; Angewandte Chemie - International Edition; vol. 41; nb. 14; (2002); p. 2541 - 2543 View in Reaxys

H N

O N

Rx-ID: 9857053 View in Reaxys 203/502 Yield

Conditions & References With hydrogenchloride in dichloromethane, Time= 2h, T= 20 °C Hamilakis, Stylianos; Tsolomitis, Athanase; Heterocyclic Communications; vol. 11; nb. 2; (2005); p. 149 - 152 View in Reaxys

(v5)

(v5) (v5)

(v12) (v5)

(v5)

Rx-ID: 26592284 View in Reaxys 204/502 Yield

Conditions & References With H2O, hydrolysis on silica gel Walsh, Patrick J.; Hollander, Frederick J.; Bergman, Robert G.; Journal of the American Chemical Society; vol. 110; (1988); p. 8729 - 8731 ; (from Gmelin) View in Reaxys

(v5)

(v5) (v5)

O N Zr (v12) (v5)

(v5)

Rx-ID: 26593091 View in Reaxys 205/502 Yield

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(v5)

(v5) (v5)

(v5)

(v12) (v5)

(v5)

Rx-ID: 26593143 View in Reaxys 206/502 Yield

O Cl

Rx-ID: 699315 View in Reaxys 207/502 Yield

Conditions & References With aluminium trichloride, anschliessendes Kochen Mason; Terry; Journal of the American Chemical Society; vol. 62; (1940); p. 1622 View in Reaxys

Rx-ID: 2879643 View in Reaxys 208/502 Yield

F O

HO racemate

racemate

Rx-ID: 3821347 View in Reaxys 209/502 Yield

Conditions & References

12 %, 85 % With silicon tetrafluoride, N-ethyl-N,N-diisopropylamine in 1,2-dichloro-ethane Shimizu, Makoto; Yoshioka, Hirosuke; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4101 - 4104 View in Reaxys 39 %, 31 % With silicon tetrafluoride in 1,2-dichloro-ethane Shimizu, Makoto; Yoshioka, Hirosuke; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4101 - 4104 View in Reaxys With silicon tetrafluoride in 1,2-dichloro-ethane, effect of various additives, Product distribution, Mechanism Shimizu, Makoto; Yoshioka, Hirosuke; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4101 - 4104 View in Reaxys 5 %Spectr. Stage 1: With boron trifluoride diethyl etherate in dichloromethane, Time= 0.0833333h, T= -20 °C Stage 2: With water, sodium hydrogencarbonate in dichloromethane, stereoselective reaction

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Cresswell, Alexander J.; Davies, Stephen G.; Lee, James A.; Roberts, Paul M.; Russell, Angela J.; Thomson, James E.; Tyte, Melloney J.; Organic Letters; vol. 12; nb. 13; (2010); p. 2936 - 2939 View in Reaxys

<<(C5Me5)Rh(μ-CH2)>2(Ph) (CO)>PF6

Rx-ID: 6208218 View in Reaxys 210/502 Yield

Conditions & References

0.0004 mmol, 0.0004 mmol, 0.006 mmol, 0.0012 mmol

With carbon monoxide in acetone, Time= 6h, T= 25 °C

0.0004 mmol, 0.0004 mmol, 0.0012 mmol, 0.006 mmol

With carbon monoxide in acetone, Time= 6h, T= 25 °C

Wang, Zhi-Qiang; Long, Helen C.; Turner, Michael L.; Maitlis, Peter M.; Journal of the Chemical Society, Chemical Communications; nb. 10; (1995); p. 1089 - 1091 View in Reaxys

O I

O N

Rx-ID: 8711263 View in Reaxys 211/502 Yield

Conditions & References

54 %, 20 %, 25 %

With sodium tetrahydroborate in ethanol, Reduction Yusubov; Perederina; Kulmanakova; Filimonov; Chi, Ki-Whan; Russian Journal of Organic Chemistry; vol. 35; nb. 9; (1999); p. 1264 - 1272 View in Reaxys

M g

Rx-ID: 15086974 View in Reaxys 212/502 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran / 0.5 h / -30 °C 1.2: 68 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 40 percent / Sphingomonas paucimobilis NCIMB 8195 / dimethylformamide; H2O; various solvent(s) / 120 h With n-butyllithium, Sphingomonas paucimobilis NCIMB 8195 in tetrahydrofuran, water, N,N-dimethyl-formamide Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys

Rx-ID: 19070353 View in Reaxys 213/502

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Yield

Conditions & References Reaction Steps: 3 1: lithium diisopropylamide / THF 2: 64 percent / Pd(PPh3)4 / benzene / 1 h / 25 °C 3: 89 percent / TiCl4 / CH2Cl2; H2O / 25 °C With tetrakis(triphenylphosphine) palladium(0), titanium tetrachloride, lithium diisopropyl amide in dichloromethane, water, benzene Takai; Sato; Oshima; Nozaki; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 108 - 115 View in Reaxys Reaction Steps: 3 1: Pd(PPh3)4 / benzene 2: 64 percent / Pd(PPh3)4 / benzene / 1 h / 25 °C 3: 89 percent / TiCl4 With tetrakis(triphenylphosphine) palladium(0), titanium tetrachloride in benzene Sato, Mitsuyoshi; Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Tetrahedron Letters; vol. 22; nb. 17; (1981); p. 1609 - 1612 View in Reaxys

O P

Rx-ID: 19079306 View in Reaxys 214/502 Yield

Conditions & References Reaction Steps: 2 1: 64 percent / Pd(PPh3)4 / benzene / 1 h / 25 °C 2: 89 percent / TiCl4 / CH2Cl2; H2O / 25 °C With tetrakis(triphenylphosphine) palladium(0), titanium tetrachloride in dichloromethane, water, benzene Takai; Sato; Oshima; Nozaki; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 108 - 115 View in Reaxys Reaction Steps: 2 1: 64 percent / Pd(PPh3)4 / benzene / 1 h / 25 °C 2: 89 percent / TiCl4 With tetrakis(triphenylphosphine) palladium(0), titanium tetrachloride in benzene Sato, Mitsuyoshi; Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Tetrahedron Letters; vol. 22; nb. 17; (1981); p. 1609 - 1612 View in Reaxys

N N

Rx-ID: 20995590 View in Reaxys 215/502 Yield

Conditions & References Reaction Steps: 2 1: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, a) -78 deg C, 4 h, b) ambient temperature, 12 h 2: 77 percent / aq. HCl / tetrahydrofuran; H2O / 24 h / Ambient temperature

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With hydrogenchloride, n-butyllithium in tetrahydrofuran, water Katritzky, Alan R.; Yang, Zhijun; Lam, Jamshed N.; Journal of Organic Chemistry; vol. 56; nb. 24; (1991); p. 6917 - 6923 View in Reaxys

H C–

CH –2

Rx-ID: 21150460 View in Reaxys 216/502 Yield

Conditions & References Reaction Steps: 2 1: KH / tetrahydrofuran 2: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 - 5 °C With n-butyllithium, potassium hydride in tetrahydrofuran, hexane Trimitsis, G. B.; Hinkley, J. M.; TenBrink, R.; Faburada, A. L.; Anderson, R.; et al.; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 2957 - 2962 View in Reaxys

Cl O

Rx-ID: 21152547 View in Reaxys 217/502 Yield

Conditions & References Reaction Steps: 3 1: BF3*EtO2 / CH2Cl2 / 48 h / Heating 2: HOAc, Zn dust / diethyl ether 3: H2O / 230 °C With boron trifluoride diethyl etherate, acetic acid, zinc in diethyl ether, dichloromethane, water Dave, Vinod; Warnhoff, E. W.; Journal of Organic Chemistry; vol. 48; nb. 15; (1983); p. 2590 - 2598 View in Reaxys Br

O O

Rx-ID: 21171341 View in Reaxys 218/502 Yield

Conditions & References Reaction Steps: 2 1: HOAc, Zn dust / diethyl ether 2: 66 mg / H2O / 230 °C With acetic acid, zinc in diethyl ether, water Dave, Vinod; Warnhoff, E. W.; Journal of Organic Chemistry; vol. 48; nb. 15; (1983); p. 2590 - 2598 View in Reaxys

O O O

Rx-ID: 21172206 View in Reaxys 219/502 Yield

Conditions & References Reaction Steps: 2 1: HOAc, Zn dust / diethyl ether 2: H2O / 230 °C With acetic acid, zinc in diethyl ether, water

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Dave, Vinod; Warnhoff, E. W.; Journal of Organic Chemistry; vol. 48; nb. 15; (1983); p. 2590 - 2598 View in Reaxys

Rx-ID: 21234935 View in Reaxys 220/502 Yield

Conditions & References Reaction Steps: 2 1: NaN3 / dioxane; H2O / 23 h / Heating 2: 50 percent / nitrosonium tetrafluoroborate / acetonitrile / 0.08 h / 0 °C With sodium azide, NOBF4 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

H N

H 2N

Rx-ID: 40121035 View in Reaxys 221/502 Yield

Conditions & References

18 %, 13 %, 22 %

With copper(l) iodide, caesium carbonate in acetonitrile, Time= 12h, T= 90 °C , Schlenk technique Xing, Qi; Lv, Hui; Xia, Chungu; Li, Fuwei; Chemistry - A European Journal; vol. 21; nb. 23; (2015); p. 8591 - 8596 View in Reaxys

Rx-ID: 279474 View in Reaxys 222/502 Yield

Conditions & References With sulfuric acid, T= -15 °C Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys With ethanol, mercury dichloride, im Rohr Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys With sulfuric acid Danilow; Zhurnal Obshchei Khimii; vol. 18; (1948); p. 2000,2006; ; (1949); p. 4632 View in Reaxys

O O

Rx-ID: 1441441 View in Reaxys 223/502 Yield

Conditions & References With silver trifluoroacetate, sodium carbonate Hill,A.E.; Hoffmann,H.M.R.; Journal of the American Chemical Society; vol. 96; (1974); p. 4597 - 4603

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View in Reaxys

H C–

Rx-ID: 1710385 View in Reaxys 224/502 Yield

Conditions & References

94 %

Time= 1.25h, Irradiation Fox, Marye Anne; Younathan, Janet; Fryxell, Glen E.; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 3109 - 3112 View in Reaxys

O O

Rx-ID: 1718717 View in Reaxys 225/502 Yield

Conditions & References

10 % With diiodo monosilane in chloroform-d1, Time= 2h, Ambient temperature Spectr., 90 % Spectr. Keinan, E.; Perez, D.; Sahai, M.; Shvily, R.; Journal of Organic Chemistry; vol. 55; nb. 9; (1990); p. 2927 - 2938 View in Reaxys

H Z

O racemate

Rx-ID: 2005280 View in Reaxys 226/502 Yield

Conditions & References With pyridine 1-oxide, oxochromium(V) complex of dichloro tetramethylsalen IIf in acetonitrile, T= 23 °C , effect of donor ligands; ligand-induced cleavage of olefins by oxochromium(V); (18)O-labeling studies of oxochromium(V), Rate constant, Mechanism Samsel, E. G.; Srinivasan, K.; Kochi, J. K.; Journal of the American Chemical Society; vol. 107; nb. 25; (1985); p. 7606 - 7617 View in Reaxys

NH 2

Rx-ID: 2565420 View in Reaxys 227/502 Yield

Conditions & References

53 %

With hydrogenchloride, Heating Celerier, Jean-Pierre; Deloisy, Elisabeth; Kapron, Pierre; Lhommet, Gerard; Maitte, Pierre; Synthesis; nb. 2; (1981); p. 130 - 133 View in Reaxys

Li+ B–

Rx-ID: 2627843 View in Reaxys 228/502

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Yield

Conditions & References

65 %, 8 %, With sodium hydroxide, methanesulfonic acid, dihydrogen peroxide, 1.) THF, -78 deg C, warming to 25 deg C, 1h, 11 % Yield given. Multistep reaction. Further byproducts given Pelter, Andrew; Drake, Robert A.; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4181 - 4184 View in Reaxys 65 %, 8 %, With sodium hydroxide, methanesulfonic acid, dihydrogen peroxide, 1.) THF, -78 deg C, warming to 25 deg C, 1h, 7% Yield given. Multistep reaction. Further byproducts given Pelter, Andrew; Drake, Robert A.; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4181 - 4184 View in Reaxys

O O

Rx-ID: 3020321 View in Reaxys 229/502 Yield

Conditions & References in water, T= 230 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Dave, Vinod; Warnhoff, E. W.; Journal of Organic Chemistry; vol. 48; nb. 15; (1983); p. 2590 - 2598 View in Reaxys

O O

Rx-ID: 3523154 View in Reaxys 230/502 Yield

Conditions & References

11 % Chro- With potassium tert-butylate in dimethyl sulfoxide, Time= 1h, Irradiation mat., 88 % Borosky, Gabriela L.; Pierini, Adriana B.; Rossi, Roberto A.; Journal of Organic Chemistry; vol. 57; nb. 1; (1992); Chromat. p. 247 - 252 View in Reaxys 88 % Chro- With potassium tert-butylate in dimethyl sulfoxide, Time= 1h, Irradiation mat., 11 % Borosky, Gabriela L.; Pierini, Adriana B.; Rossi, Roberto A.; Journal of Organic Chemistry; vol. 57; nb. 1; (1992); Chromat. p. 247 - 252 View in Reaxys

F O

HO racemate

racemate

Rx-ID: 3821336 View in Reaxys 231/502 Yield

Conditions & References

11 %, 78 % With silicon tetrafluoride, N-ethyl-N,N-diisopropylamine in 1,2-dichloro-ethane Shimizu, Makoto; Yoshioka, Hirosuke; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4101 - 4104 View in Reaxys

O O N N

Rx-ID: 3917031 View in Reaxys 232/502 Yield 79 %

Conditions & References With rhodium(II) trifluoroacetate dimer, Time= 1h, Ambient temperature

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McKervey, M. Anthony; Russell, D. Noel; Twohig, M. Fiona; Journal of the Chemical Society, Chemical Communications; nb. 8; (1985); p. 491 - 492 View in Reaxys

H 2N

Rx-ID: 10535722 View in Reaxys 233/502 Yield

Conditions & References

75 %

Stage 1: With tetrafluoroboric acid, HNO2 Stage 2: With copper(I) oxide, sodium acetate, Meerwein arylation Li, Li; Chen, Hongbiao; Lin, Yuanbin; Synthetic Communications; vol. 37; nb. 6; (2007); p. 985 - 991 View in Reaxys

Rx-ID: 29399692 View in Reaxys 234/502 Yield

Conditions & References

62 %Chro- With Ni(bpy)(CH3SO3)2 in N,N-dimethyl-formamide, T= 20 °C , Ionic liquid, Electrochemical reaction mat., 29 %Chromat. Barhdadi, Rachid; Maekawa, Hirofumi; Comminges, Clement; Troupel, Michel; Bulletin of the Chemical Society of Japan; vol. 82; nb. 12; (2009); p. 1510 - 1513 View in Reaxys

Rx-ID: 31525177 View in Reaxys 235/502 Yield

Conditions & References With 12-molybdophosphoric acid HPMo, dihydrogen peroxide in water, acetonitrile, Time= 2h, T= 50 °C Armatas, Gerasimos S.; Bilis, Georgios; Louloudi, Maria; Journal of Materials Chemistry; vol. 21; nb. 9; (2011); p. 2997 - 3005 View in Reaxys

O O

Rx-ID: 31820306 View in Reaxys 236/502 Yield

Conditions & References With water-d2 in acetonitrile-D3, Time= 3h, T= 20 °C , UV-irradiation Murase, Takashi; Takezawa, Hiroki; Fujita, Makoto; Chemical Communications; vol. 47; nb. 39; (2011); p. 10960 10962 View in Reaxys

O H

Rx-ID: 38389795 View in Reaxys 237/502 Yield

Conditions & References Reaction Steps: 2 1: potassium hydroxide; water / methanol

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2: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / |Enzymatic reaction With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, water, nicotinamide adenine dinucleotide phosphate, potassium hydroxide in methanol Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys

O HO O

Rx-ID: 39153177 View in Reaxys 238/502 Yield 38 %

Conditions & References With magnesium oxide, Time= 6h, T= 210 °C , Meerwein-Ponndorf-Verley Reduction Pasini, Thomas; Lolli, Alice; Albonetti, Stefania; Cavani, Fabrizio; Mella, Massimo; Journal of Catalysis; vol. 317; (2014); p. 206 - 219 View in Reaxys

N O

Rx-ID: 786070 View in Reaxys 239/502 Yield

Conditions & References With ethanol, nickel, Hydrogenation Rupe; Metzger; Vogler; Helvetica Chimica Acta; vol. 8; (1925); p. 850 View in Reaxys With sulfuric acid, Hydrolysis Julian; Oliver; Organic Syntheses; vol. 18; (1938); p. 54 View in Reaxys With sulfuric acid, water, Heating, Yield given Kuchar; Brunova; Rejholec; et al.; Collection of Czechoslovak Chemical Communications; vol. 49; nb. 1; (1984); p. 122 - 136 View in Reaxys Reaction Steps: 2 Hermanns; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 85; (1913); p. 234 View in Reaxys

Rx-ID: 2036659 View in Reaxys 240/502 Yield

Conditions & References With sulfuric acid, sodium iodide in tetrahydrofuran, water, Time= 2h, Ambient temperature, Yield given Gemal, A.L.; Luche, J.L.; Tetrahedron Letters; vol. 21; (1980); p. 3195 - 3198 View in Reaxys

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Br O

Rx-ID: 2064199 View in Reaxys 241/502 Yield

Conditions & References

88 % Spectr.

With sulfuric acid, sodium iodide in tetrahydrofuran, water, Time= 0.5h, Ambient temperature Gemal, A.L.; Luche, J.L.; Tetrahedron Letters; vol. 21; (1980); p. 3195 - 3198 View in Reaxys

O I O

Rx-ID: 2533641 View in Reaxys 242/502 Yield

O Se O

Rx-ID: 2551914 View in Reaxys 243/502 Yield

Conditions & References With hydrogen bromide in diethyl ether, Yield given Back, Thomas G.; Kerr, Russell G.; Tetrahedron; vol. 41; nb. 21; (1985); p. 4759 - 4764 View in Reaxys

H Si O

Rx-ID: 2679667 View in Reaxys 244/502 Yield

Conditions & References

12 %, 15 %, 37 %, 12 %

With triethylamine in methanol, dichloromethane, Time= 16h, Ambient temperature

15 %, 37 %, 12 %, 12 %

With triethylamine in methanol, dichloromethane, Time= 16h, Ambient temperature

12 %, 37 %, 12 %, 15 %

With triethylamine in methanol, dichloromethane, Time= 16h, Ambient temperature

12 %, 15 %, 12 %, 37 %

With triethylamine in methanol, dichloromethane, Time= 16h, Ambient temperature

Hashimoto, Norio; Aoyama, Toyohiko; Shioiri, Takayuki; Heterocycles; vol. 15; nb. 2; (1981); p. 975 - 979 View in Reaxys

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benzylethylene oxide Rx-ID: 6046453 View in Reaxys 245/502 Yield

Conditions & References With aluminum oxide, T= 260 °C Levy; Sfiras; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 184; (1927); p. 1337 View in Reaxys With zinc(II) chloride Levy; Sfiras; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 184; (1927); p. 1337 View in Reaxys

biscyclopentadienyl titanium-μ-chloro-μmethylidene bismethyl aluminum

Rx-ID: 6046454 View in Reaxys 246/502 Yield

Conditions & References

35 %

in tetrahydrofuran, toluene, -40 deg C 30 min; room temperature, 3 h Chou, Ta-Shue; Huang, Sung-Ben; Tetrahedron Letters; vol. 24; nb. 21; (1983); p. 2169 - 2170 View in Reaxys

O O O O racemate

Rx-ID: 9033673 View in Reaxys 247/502 Yield

Conditions & References

25 %

in acetonitrile, Time= 1h, Photolysis Linder, Sorana; White, Katherine; Palmer, Mandelin; Arney, Benny; White, Rick; Tetrahedron Letters; vol. 43; nb. 7; (2002); p. 1169 - 1170 View in Reaxys Reaction Steps: 2 1: acetonitrile / Photolysis 2: 25 percent / acetonitrile / 1 h / Photolysis in acetonitrile Linder, Sorana; White, Katherine; Palmer, Mandelin; Arney, Benny; White, Rick; Tetrahedron Letters; vol. 43; nb. 7; (2002); p. 1169 - 1170 View in Reaxys

O S S

Rx-ID: 11547919 View in Reaxys 248/502 Yield

Conditions & References Reaction Steps: 2 1: 80 percent / lithium diisopropylamide / 1 h / -78 °C 2: 87 percent / sulfuric acid / toluene / 1 h / 100 °C With sulfuric acid, lithium diisopropyl amide in toluene

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Yoshida, Suguru; Yorimitsu, Hideki; Oshima, Koichiro; Synlett; nb. 10; (2007); p. 1622 - 1624 View in Reaxys

Cl O

Rx-ID: 11739207 View in Reaxys 249/502 Yield

Conditions & References Reaction Steps: 2 1: 70 percent / AgClO4 / nitromethane 2: 2.) 10percent HCl / 1.) ether With hydrogenchloride, silver perchlorate in nitromethane Mezheritskaya, L. V.; Matsovskaya, E. S.; Dorofeenko, G. N.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 174 - 178; Zhurnal Organicheskoi Khimii; vol. 16; nb. 1; (1980); p. 183 - 188 View in Reaxys Reaction Steps: 3 1: toluene; acetic acid ester 2: sodium / 0 °C 3: KOH-solution With potassium hydroxide, acetic acid ester, sodium, toluene Morgan; Drew; Porter; Chemische Berichte; vol. 58; (1925); p. 338 View in Reaxys O N O

<2.4-dioxy-phenyl>-benzyl ke‐ tone

Rx-ID: 20379062 View in Reaxys 250/502 Yield

Conditions & References Reaction Steps: 2 1: 75 percent / 5 h / Heating 2: 12 N aq. HCl / CHCl3 / 1 h / 50 °C With hydrogenchloride in chloroform Trapani, Giuseppe; Reho, Antonia; Latrofa, Andrea; Liso, Gaetano; Synthesis; nb. 1; (1988); p. 84 - 87 View in Reaxys

O N

<2.4-dioxy-phenyl>-benzyl ke‐ tone

Rx-ID: 20402374 View in Reaxys 251/502 Yield

Conditions & References Reaction Steps: 2 1: 70 percent / 20 h / Heating 2: 12 N aq. HCl / CHCl3 / 1 h / 50 °C With hydrogenchloride in chloroform Trapani, Giuseppe; Reho, Antonia; Latrofa, Andrea; Liso, Gaetano; Synthesis; nb. 1; (1988); p. 84 - 87

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View in Reaxys

NH S

<2.4-dioxy-phenyl>-benzyl ke‐ tone Rx-ID: 20420344 View in Reaxys 252/502

Yield

Conditions & References Reaction Steps: 3 1: 89 percent / room temp., overnight then reflux, 1 h 2: 75 percent / 5 h / Heating 3: 12 N aq. HCl / CHCl3 / 1 h / 50 °C With hydrogenchloride in chloroform Trapani, Giuseppe; Reho, Antonia; Latrofa, Andrea; Liso, Gaetano; Synthesis; nb. 1; (1988); p. 84 - 87 View in Reaxys

N N

Rx-ID: 20686217 View in Reaxys 253/502 Yield

Conditions & References Reaction Steps: 2 1: TFA / CH2Cl2 / 18 h / 25 °C 2: 69 percent / oxalic acid, water / diethyl ether / 18 h With water, oxalic acid, trifluoroacetic acid in diethyl ether, dichloromethane Baldwin, Jack E.; Adlington, Robert M.; Bottaro, Jeffrey C.; Kolhe, Jayant N.; Perry, Matthew W. D.; Jain, Ashok U.; Tetrahedron; vol. 42; nb. 15; (1986); p. 4223 - 4234 View in Reaxys

O S O S

Rx-ID: 21484191 View in Reaxys 254/502 Yield

Conditions & References Reaction Steps: 2 1: NaH / dimethylformamide / 19 h / Ambient temperature 2: different reagents and reaction times / methanol / Heating With sodium hydride in methanol, N,N-dimethyl-formamide Ogura, Katsuyuki; Ohtsuki, Kazuo; Nakamura, Masami; Yahata, Nobuhiro; Takahashi, Kazumasa; Iida, Hirotada; Tetrahedron Letters; vol. 26; nb. 20; (1985); p. 2455 - 2458 View in Reaxys

O S

Rx-ID: 21533027 View in Reaxys 255/502 Yield

Conditions & References Reaction Steps: 2 1: 89 percent / 1N aq. HCl / tetrahydrofuran

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2: 67 percent / aluminium amalgam / tetrahydrofuran; H2O / Heating With hydrogenchloride, aluminium amalgam in tetrahydrofuran, water Barre, V.; Massias, F.; Uguen, D.; Tetrahedron Letters; vol. 30; nb. 52; (1989); p. 7389 - 7392 View in Reaxys

O O

Rx-ID: 28177227 View in Reaxys 256/502 Yield

Conditions & References With 1-(4-methoxyphenyl)ethanone in toluene, UV-irradiation, Inert atmosphere Portela-Cubillo, Fernando; Lymer, James; Scanlan, Eoin M.; Scott, Jackie S.; Walton, John C.; Tetrahedron; vol. 64; nb. 52; (2008); p. 11908 - 11916 View in Reaxys

O B–

Li+

Rx-ID: 2622772 View in Reaxys 257/502 Yield

Conditions & References

4 %, 83 %, With iodine in tetrahydrofuran, diethyl ether, from -78 deg C to 25 deg C 8% Pelter, Andrew; Drake, Robert A.; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4181 - 4184 View in Reaxys

Cl –

Rx-ID: 3756880 View in Reaxys 258/502 Yield

Conditions & References With chloride in gas, T= 148 °C , p= 0 - 0.2Torr , ΔGo, Equilibrium constant, Thermodynamic data French, M. A.; Ikuta, S.; Kebarle, P.; Canadian Journal of Chemistry; vol. 60; (1982); p. 1907 - 1918 View in Reaxys

Rx-ID: 4379737 View in Reaxys 259/502 Yield 46 %, 13 %, 8 %, 6 %

Conditions & References T= 600 °C Oyewale, A. O.; Aitken, R. A.; Russian Chemical Bulletin; vol. 44; nb. 5; (1995); p. 919 - 922; Izvestiya Akademi Nauk, Seriya Khimicheskaya; nb. 5; (1995); p. 946 - 949 View in Reaxys

13 %, 8 %, T= 600 °C 6 %, 46 % Oyewale, A. O.; Aitken, R. A.; Russian Chemical Bulletin; vol. 44; nb. 5; (1995); p. 919 - 922; Izvestiya Akademi Nauk, Seriya Khimicheskaya; nb. 5; (1995); p. 946 - 949 View in Reaxys 46 %, 8 %, T= 600 °C 6 %, 46 %

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Oyewale, A. O.; Aitken, R. A.; Russian Chemical Bulletin; vol. 44; nb. 5; (1995); p. 919 - 922; Izvestiya Akademi Nauk, Seriya Khimicheskaya; nb. 5; (1995); p. 946 - 949 View in Reaxys 46 %, 13 %, 6 %, 8 %

T= 600 °C Oyewale, A. O.; Aitken, R. A.; Russian Chemical Bulletin; vol. 44; nb. 5; (1995); p. 919 - 922; Izvestiya Akademi Nauk, Seriya Khimicheskaya; nb. 5; (1995); p. 946 - 949 View in Reaxys

O O

Rx-ID: 5256325 View in Reaxys 260/502 Yield 94 % Spectr., 6 % Spectr.

Conditions & References With iron(III) tetraphenylporphyrin triflate in 1,4-dioxane, Heating, Rearrangement Suda, Kohji; Baba, Kenji; Nakajima, Shin-ichiro; Takanami, Toshikatsu; Tetrahedron Letters; vol. 40; nb. 40; (1999); p. 7243 - 7246 View in Reaxys

α-methyl-α-phenyl-ethylene ox‐ ide

Rx-ID: 6046443 View in Reaxys 261/502 Yield

(+-)-3-oxo-2-phenyl-butyronitrile Rx-ID: 6046447 View in Reaxys 262/502 Yield

Conditions & References With phosphoric acid, T= 150 °C Bobranskii; Drabik; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 14; (1941); p. 410,413; ; (1942); p. 2531 View in Reaxys 2H

Rx-ID: 9897268 View in Reaxys 263/502 Yield

Conditions & References With [Ir(cod)2]BF4, triphenyl-arsane, deuterium in dichloromethane, Time= 120h, Title compound not separated from byproducts Herbert, John M.; Kohler, Andrew D.; McNeill, Alan H.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 48; nb. 4; (2005); p. 285 - 294 View in Reaxys With [Ir(cod)2]BF4, 1,2-bis[(diphenylarsino)]ethane, deuterium in dichloromethane, Time= 120h, Title compound not separated from byproducts

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Herbert, John M.; Kohler, Andrew D.; McNeill, Alan H.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 48; nb. 4; (2005); p. 285 - 294 View in Reaxys

O O

Rx-ID: 10302195 View in Reaxys 264/502 Yield

Conditions & References With TEA, Time= 48h, T= 20 °C , Dakin-West reaction Tran, Khanh-Van; Bickar, David; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6640 - 6643 View in Reaxys

Rx-ID: 10302196 View in Reaxys 265/502 Yield

Conditions & References With 1-methyl-1H-imidazole, Time= 12h, T= 20 °C , Dakin-West reaction Tran, Khanh-Van; Bickar, David; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6640 - 6643 View in Reaxys

(E)-n-C6H13CH=CHZrCp2Cl

Rx-ID: 11727808 View in Reaxys 266/502 Yield

Conditions & References Reaction Steps: 3 1: sodium ethoxide / benzene / 5 h / 60 - 65 °C 2: aq.NaOH / 3 h / 75 - 80 °C 3: 3 h / 200 - 220 °C With sodium hydroxide, sodium ethanolate in benzene Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953 View in Reaxys Reaction Steps: 3 1: sodium ethoxide / benzene / 5 h / 60 - 65 °C 2: aq.NaOH / 3 h / 75 - 80 °C 3: 3 h / 200 - 220 °C With sodium hydroxide, sodium ethanolate in benzene Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953 View in Reaxys

O O

α.α'-diphenyl-acetone Rx-ID: 19441384 View in Reaxys 267/502

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Yield

Conditions & References Reaction Steps: 2 1: 44 percent 2: SO2Cl2 / CH2Cl2 / 1.) 0 deg C, 2.) room temperature With sulfuryl dichloride in dichloromethane Benneche, Tore; Christiansen, Mette L.; Undheim, Kjell; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 40; nb. 8; (1986); p. 700 - 702 View in Reaxys Reaction Steps: 2 1: 44 percent 2: Br2 / CCl4 / 1.) -20 deg C, 2.) room temperature With bromine in tetrachloromethane Benneche, Tore; Christiansen, Mette L.; Undheim, Kjell; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 40; nb. 8; (1986); p. 700 - 702 View in Reaxys

<2.4-dioxy-phenyl>-benzyl ke‐ tone

O S O S

Rx-ID: 20177413 View in Reaxys 268/502 Yield

Conditions & References Reaction Steps: 2 1: NaH / dimethylformamide / 19 h / Ambient temperature 2: cc. HCl / methanol / Heating With hydrogenchloride, sodium hydride in methanol, N,N-dimethyl-formamide Ogura, Katsuyuki; Ohtsuki, Kazuo; Takahashi, Kazumasa; Iida, Hirotada; Chemistry Letters; (1986); p. 1597 1598 View in Reaxys

aminoguanidine salt O

<2.4-dioxy-phenyl>-benzyl ke‐ tone Rx-ID: 20179341 View in Reaxys 269/502

Yield

Conditions & References Reaction Steps: 4 1: 85 percent / K2CO3 / propan-2-ol / Heating 2: 97 percent / NaBH4 / ethanol / 2 h / Ambient temperature 3: NaH / dimethylformamide / 19 h / Ambient temperature 4: cc. HCl / methanol / Heating With hydrogenchloride, sodium tetrahydroborate, sodium hydride, potassium carbonate in methanol, ethanol, N,Ndimethyl-formamide, isopropyl alcohol Ogura, Katsuyuki; Ohtsuki, Kazuo; Takahashi, Kazumasa; Iida, Hirotada; Chemistry Letters; (1986); p. 1597 1598 View in Reaxys

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<2.4-dioxy-phenyl>-benzyl ke‐ tone

O S O S

Rx-ID: 20180612 View in Reaxys 270/502 Yield

Conditions & References Reaction Steps: 3 1: 97 percent / NaBH4 / ethanol / 2 h / Ambient temperature 2: NaH / dimethylformamide / 19 h / Ambient temperature 3: cc. HCl / methanol / Heating With hydrogenchloride, sodium tetrahydroborate, sodium hydride in methanol, ethanol, N,N-dimethyl-formamide Ogura, Katsuyuki; Ohtsuki, Kazuo; Takahashi, Kazumasa; Iida, Hirotada; Chemistry Letters; (1986); p. 1597 1598 View in Reaxys

O S O

Rx-ID: 20775663 View in Reaxys 271/502 Yield

Conditions & References Reaction Steps: 2 1: 81 percent / 1.3 eq. NaH / dimethylformamide / 1.) room temp., 90.5 h., 2.) 60 deg C, 3 h. 2: 86 percent / conc. hydrochloric acid / methanol / 2 h / Heating With hydrogenchloride, sodium hydride in methanol, N,N-dimethyl-formamide Ogura, Katsuyuki; Suzuki, Michiyo; Watanabe, Jun-ichi; Yamashita, Mitsuo; Iida, Hirotada; Tsuchihashi, Genichi; Chemistry Letters; (1982); p. 813 - 814 View in Reaxys

O Br

Rx-ID: 32026277 View in Reaxys 272/502 Yield

Conditions & References Reaction Steps: 2 1: magnesium / tetrahydrofuran 2: palladium diacetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 50 °C / 760.05 Torr With palladium diacetate, magnesium, 2,3-dicyano-5,6-dichloro-p-benzoquinone in tetrahydrofuran, acetonitrile Chen, Huoji; Cai, Congbi; Liu, Xiaohang; Li, Xianwei; Jiang, Huanfeng; Chemical Communications; vol. 47; nb. 44; (2011); p. 12224 - 12226 View in Reaxys Reaction Steps: 2 1: magnesium / tetrahydrofuran 2: tert.-butylhydroperoxide; carbon monoxide; palladium diacetate / methanol; acetonitrile / 50 °C / 760.05 Torr With tert.-butylhydroperoxide, carbon monoxide, palladium diacetate, magnesium in tetrahydrofuran, methanol, acetonitrile Chen, Huoji; Cai, Congbi; Liu, Xiaohang; Li, Xianwei; Jiang, Huanfeng; Chemical Communications; vol. 47; nb. 44; (2011); p. 12224 - 12226 View in Reaxys

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N O

Rx-ID: 9993 View in Reaxys 273/502 Yield

Conditions & References With methanol, diethyl ether, T= 20 °C Mosettig; Jovanovic; Monatshefte fuer Chemie; vol. 53/54; (1929); p. 435 View in Reaxys

O O

Rx-ID: 2005263 View in Reaxys 274/502 Yield

Conditions & References With pyridine 1-oxide, iodosylbenzene, lt;(8S,8S')-3,3'-bislt;(R)-1-phenylpropylgt;-4,4'-dimethyl-8,8'-diphenylsalengt;manganese(III) hexafluorophosphate in dichloromethane, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Irie; Noda; Ito; Matsumoto; Katsuki; Tetrahedron Asymmetry; vol. 2; nb. 7; (1991); p. 481 - 494 View in Reaxys

O S Si

O Si

Si O

N O

Rx-ID: 2130826 View in Reaxys 275/502 Yield

Conditions & References

10 % Chromat., 4 % Chromat., 86 % Chromat.

in tetrahydrofuran, T= 20 °C

4 % Chromat., 86 % Chromat., 10 % Chromat.

in tetrahydrofuran, Time= 5h, T= 20 °C

Nakajima, Tadashi; Segi, Masahito; Sugimoto, Fumitosi; Hioki, Reiko; Yokota, Seiko; Miyashita, Kiyoshi; Tetrahedron; vol. 49; nb. 37; (1993); p. 8343 - 8358 View in Reaxys

Rx-ID: 2147478 View in Reaxys 276/502 Yield

Conditions & References With dimethyl amine in benzene Bargagna, Alberto; Evangelisti, Filippo; Schenone, Pietro; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 111 - 116 View in Reaxys

Rx-ID: 3695117 View in Reaxys 277/502

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Yield

Conditions & References With oxalic acid in diethyl ether, water, Time= 14h, Yield given Adlington, Robert M.; Baldwin, Jack E.; Bottaro, Jeffrey C.; Perry, Matthew W. D.; Journal of the Chemical Society, Chemical Communications; nb. 18; (1983); p. 1040 - 1041 View in Reaxys

H C– Li+

Rx-ID: 3843219 View in Reaxys 278/502 Yield

Conditions & References With lithium diisopropyl amide in tetrahydrofuran Ali, Syed Mashhood; Tanimoto, Shigeo; Journal of the Chemical Society, Chemical Communications; nb. 11; (1989); p. 684 - 685 View in Reaxys

O P

Rx-ID: 4490121 View in Reaxys 279/502 Yield

Conditions & References

31 %

in methanol, Time= 0.5h, T= 20 - 25 °C , Irradiation Nakamura, Mitsunobu; Okamoto, Yoshiki; Takamuku, Setsuo; Chemical Communications; nb. 2; (1996); p. 209 210 View in Reaxys

31 %

in methanol, Time= 0.5h, T= 20 - 25 °C , Irradiation, Quantum yield Nakamura, Mitsunobu; Okamoto, Yoshiki; Takamuku, Setsuo; Chemical Communications; nb. 2; (1996); p. 209 210 View in Reaxys

H N

Rx-ID: 4794301 View in Reaxys 280/502 Yield

Conditions & References With potassium hydroxide in methanol, Time= 1h, Heating, Yield given. Yields of byproduct given. Title compound not separated from byproducts Kafka; Kappe; Monatshefte fur Chemie; vol. 128; nb. 10; (1997); p. 1019 - 1031 View in Reaxys

O Mg Cl

etheric solution of acetyl chloride Rx-ID: 6046458 View in Reaxys 281/502

Yield

Conditions & References With diethyl ether, T= -15 - -10 °C Shishido; Kukita; Kogyo Kagaku Zasshi; vol. 48; (1945); p. 34; ; (1948); p. 6339

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View in Reaxys

methylacetylene metal salt O

Rx-ID: 14479358 View in Reaxys 282/502 Yield

Conditions & References Reaction Steps: 2 1: 63 percent / NH4OAc / 5 h / Heating 2: H2; RuCl2(PPh3)3 / CH2Cl2 / 24 h / 14710.2 Torr / Heating With tris(triphenylphosphine)ruthenium(II) chloride, ammonium acetate, hydrogen in dichloromethane Li, Yanjun; Izumi, Taeko; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 49; nb. 4; (2002); p. 505 508 View in Reaxys

lead (II)-compound of ethanethiol

Rx-ID: 17729239 View in Reaxys 283/502 Yield

Conditions & References Reaction Steps: 2 1: 92 percent / diethyl ether 2: 1.) Bu3SnH, di-tert-butyl hyponitrite, 2.) aq. KF / 1.) C6H6, 60 deg C, 0.5 h, 2.) Et2O With potassium fluoride, tri-n-butyl-tin hydride, t-BuON=NOt-Bu in diethyl ether Dang, Hai-Shan; Roberts, Brian P.; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1996); p. 769 775 View in Reaxys

Rx-ID: 18536928 View in Reaxys 284/502 Yield

Conditions & References Reaction Steps: 2 1: trifluoroacetic acid / 6 h / 20 °C 2: (CO2H)2 / H2O; diethyl ether / 14 h With oxalic acid in diethyl ether, water, trifluoroacetic acid Adlington, Robert M.; Baldwin, Jack E.; Bottaro, Jeffrey C.; Perry, Matthew W. D.; Journal of the Chemical Society, Chemical Communications; nb. 18; (1983); p. 1040 - 1041 View in Reaxys

O B O

Rx-ID: 31719364 View in Reaxys 285/502 Yield

Conditions & References Reaction Steps: 2 1.1: potassium fluoride / ethylene glycol dimethyl ether / 18 h / 20 °C / Inert atmosphere 2.1: chloro-trimethyl-silane / ethylene glycol dimethyl ether / 0.33 h / -20 - -10 °C / Inert atmosphere 2.2: 3 h / -20 - 20 °C / Inert atmosphere With potassium fluoride, chloro-trimethyl-silane in ethylene glycol dimethyl ether

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Elkin, Pavel K.; Levin, Vitalij V.; Dilman, Alexander D.; Struchkova, Marina I.; Belyakov, Pavel A.; Arkhipov, Dmitry E.; Korlyukov, Alexander A.; Tartakovsky, Vladimir A.; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5259 - 5263 View in Reaxys

O Cl Mg

Rx-ID: 31719377 View in Reaxys 286/502 Yield

Conditions & References Reaction Steps: 3 1.1: tetrahydrofuran / -80 - 0 °C / Inert atmosphere 2.1: potassium fluoride / ethylene glycol dimethyl ether / 18 h / 20 °C / Inert atmosphere 3.1: chloro-trimethyl-silane / ethylene glycol dimethyl ether / 0.33 h / -20 - -10 °C / Inert atmosphere 3.2: 3 h / -20 - 20 °C / Inert atmosphere With potassium fluoride, chloro-trimethyl-silane in tetrahydrofuran, ethylene glycol dimethyl ether Elkin, Pavel K.; Levin, Vitalij V.; Dilman, Alexander D.; Struchkova, Marina I.; Belyakov, Pavel A.; Arkhipov, Dmitry E.; Korlyukov, Alexander A.; Tartakovsky, Vladimir A.; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5259 - 5263 View in Reaxys 2H 2H

Rx-ID: 31820302 View in Reaxys 287/502 Yield

Conditions & References Stage 1: With water-d2, Time= 1h, T= 20 °C Stage 2:Time= 6h, T= 20 °C , Inert atmosphere, UV-irradiation Murase, Takashi; Takezawa, Hiroki; Fujita, Makoto; Chemical Communications; vol. 47; nb. 39; (2011); p. 10960 10962 View in Reaxys

O E

Rx-ID: 35351222 View in Reaxys 288/502 Yield

Conditions & References Reaction Steps: 2 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C / |Schlenk technique; |Inert atmosphere 2: [Pd2H2(1,3-bis(diphenylphosphino)propane)3](TfO)2 / tetrahydrofuran / 12 h / 85 °C / |Schlenk technique; |Inert atmosphere; |Glovebox With [Pd2H2(1,3-bis(diphenylphosphino)propane)3](TfO)2, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, dichloromethane Vyas, Devendra J.; Larionov, Evgeny; Besnard, Celine; Guenee, Laure; Mazet, Clement; Journal of the American Chemical Society; vol. 135; nb. 16; (2013); p. 6177 - 6183 View in Reaxys

Rx-ID: 1587725 View in Reaxys 289/502

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Yield

Conditions & References

100 % Chromat.

With 3-chloro-benzenecarboperoxoic acid, Time= 1h, T= 25 °C Uemura, Sakae; Fukuzawa, Shin-ichi; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1985); p. 471 - 480 View in Reaxys

Rx-ID: 1587916 View in Reaxys 290/502 Yield

Conditions & References

84 % Chro- With 3-chloro-benzenecarboperoxoic acid, Time= 1h, T= 20 - 25 °C mat. Uemura, Sakae; Fukuzawa, Shin-ichi; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1985); p. 471 - 480 View in Reaxys

HO HO

racemate

Rx-ID: 1764003 View in Reaxys 291/502 Yield

Conditions & References

26.9 %, 2.9 With 2,2'-azo-bisisobutyronitrile, oxygen in chlorobenzene, T= 120 °C , p= 759.8Torr , Product distribution, Mechanism %, 3.2 %, 55.1 %, 0.8 Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 View in Reaxys %, 3.4 %

O– I

K+

Rx-ID: 1793324 View in Reaxys 292/502 Yield

Conditions & References

10 % Chromat., 4 % Chromat., 65 % Chromat.

With ammonia, T= -33 °C

65 % Chromat., 4 % Chromat., 10 % Chromat.

With ammonia, T= -33 °C

65 % Chromat., 10 % Chromat., 4 % Chromat.

With ammonia, T= -33 °C , various aryl halides; reactions of acetone enolate ion with halobenzenes, leaving group effect, Product distribution

Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

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O O

Rx-ID: 2005264 View in Reaxys 293/502 Yield

Conditions & References

12 %, 5 %

With iodosylbenzene, lt;(8S,8'S)-3,3'-bislt;(1R)-1-phenylpropylgt;-4-4'-dimethyl-8,8'-diphenylsalengt;manganese(III) in acetonitrile, Ambient temperature, Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts Irie; Noda; Ito; Katsuki; Tetrahedron Letters; vol. 32; nb. 8; (1991); p. 1055 - 1058 View in Reaxys

5 %, 12 %

With iodosylbenzene, lt;(8S,8S')-3,3'-bislt;(R)-1-phenylpropylgt;-4,4'-dimethyl-8,8'-diphenylsalengt;manganese(III) hexafluorophosphate in acetonitrile, Time= 12h, Ambient temperature, Yields of byproduct given Irie; Noda; Ito; Matsumoto; Katsuki; Tetrahedron Asymmetry; vol. 2; nb. 7; (1991); p. 481 - 494 View in Reaxys

12 %, 5 %

With iodosylbenzene, lt;(8S,8'S)-3,3'-bislt;(R)-1-phenylpropylgt;-4,4'-dimethyl-8,8'-diphenylsalengt;manganese(III) hexafluorophosphate in acetonitrile, Time= 12h, Ambient temperature, other reaction partner system and solvent; other olefin, Product distribution, Mechanism Irie; Noda; Ito; Matsumoto; Katsuki; Tetrahedron Asymmetry; vol. 2; nb. 7; (1991); p. 481 - 494 View in Reaxys

H 2N

HO H 2N

Rx-ID: 2173152 View in Reaxys 294/502 Yield

Conditions & References With pyridixamine phosphate, Time= 20h, T= 30 °C , pH 9.0. aromatic L-amino acid decarboxylase from Micrococcus percitreus Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 49; nb. 1; (1985); p. 159 - 166 View in Reaxys

O O

O P O

Rx-ID: 4472684 View in Reaxys 295/502 Yield

Conditions & References With lithium aluminium tetrahydride, sulfuric acid, sodium hydride, 1.) THF, room temperature, 1 h, 2.) THF, room temperature, 30 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

O OH O O HO racemate

Rx-ID: 4915411 View in Reaxys 296/502

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Yield

Conditions & References in acetonitrile, T= 37 °C , log A, Ea, ΔH(excit.), ΔS(excit.); var. temp., Thermodynamic data, Quantum yield Adam, Waldemar; Andler, Simone; Nau, Werner M.; Saha-Moeller, Chantu R.; Journal of the American Chemical Society; vol. 120; nb. 15; (1998); p. 3549 - 3559 View in Reaxys

O OH O O HO racemate

Rx-ID: 4915412 View in Reaxys 297/502 Yield

<(Me3Si)2N>3(cycloUCH2Si(Me2)N)SiMe3

Rx-ID: 6046450 View in Reaxys 298/502 Yield

Conditions & References

66 % Chro- in pentane, Time= 0.0833333h mat. Dormond, Alain; Elbouadili, Abdelaziz; Moise, Claude; Journal of Organic Chemistry; vol. 54; nb. 15; (1989); p. 3747 - 3748 View in Reaxys

H C

Rx-ID: 10065897 View in Reaxys 299/502 Yield

Conditions & References With ammonium cerium(IV) nitrate, benzotriazol-1-ol in acetonitrile, T= 25 °C , Kinetics Brandi, Paolo; Galli, Carlo; Gentili, Patrizia; Journal of Organic Chemistry; vol. 70; nb. 23; (2005); p. 9521 - 9528 View in Reaxys

Rx-ID: 32048482 View in Reaxys 300/502 Yield

Conditions & References Reaction Steps: 2 1.1: water / 1 h / 20 °C 1.2: 6 h / 20 °C / Inert atmosphere; UV-irradiation 2.1: water-d2 / acetonitrile-D3 / 3 h / 20 °C / UV-irradiation With water, water-d2 in acetonitrile-D3 Murase, Takashi; Takezawa, Hiroki; Fujita, Makoto; Chemical Communications; vol. 47; nb. 39; (2011); p. 10960 10962

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View in Reaxys O O

N O

Rx-ID: 1986975 View in Reaxys 301/502 Yield

Conditions & References

10 %

With tri-n-butyl-tin hydride, 3-chloro-benzenecarboperoxoic acid, 1.) methylene chloride, Multistep reaction Aizpurua, J. M.; Oiarbide, M.; Palomo, C.; Tetrahedron Letters; vol. 28; nb. 44; (1987); p. 5365 - 5366 View in Reaxys

racemate

Rx-ID: 2005268 View in Reaxys 302/502 Yield

Conditions & References

24.5 %, 4.0 With 2,2'-azo-bisisobutyronitrile, oxygen in chlorobenzene, T= 120 °C , p= 759.8Torr , Product distribution, Mechanism %, 1.8 %, 32.4 %, 7.4 Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 View in Reaxys %, 2.2 %

Rx-ID: 2399726 View in Reaxys 303/502 Yield

Conditions & References With cadmium, 1.) glyme, 20 deg C, 2.5 h, 2.) benzene, RT, 20 h, Yield given. Multistep reaction Burkhardt, Elizabeth R.; Rieke, Reuben D.; Journal of Organic Chemistry; vol. 50; nb. 3; (1985); p. 416 - 417 View in Reaxys O

N N

O O

N H

Rx-ID: 2983388 View in Reaxys 304/502 Yield

Conditions & References With 2,2'-azo-bisisobutyronitrile in tetrachloromethane, Time= 16h, Heating, Yield given Lee, Cheuk Man; Sammes, Michael P.; Katritzky, Alan R.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 2458 - 2462 View in Reaxys

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N N

O O

N H

Rx-ID: 2984616 View in Reaxys 305/502 Yield

O O

N H

N O

Rx-ID: 2987453 View in Reaxys 306/502 Yield

O O

OH HO

Rx-ID: 5231369 View in Reaxys 307/502 Yield

Conditions & References in water, T= 25 °C , Rate constant Baciocchi, Enrico; Bietti, Massimo; Manduchi, Laura; Steenken, Steen; Journal of the American Chemical Society; vol. 121; nb. 28; (1999); p. 6624 - 6629 View in Reaxys With Na2B4O7, dipotassium peroxodisulfate, T= 25 °C , Rate constant Baciocchi, Enrico; Bietti, Massimo; Manduchi, Laura; Steenken, Steen; Journal of the American Chemical Society; vol. 121; nb. 28; (1999); p. 6624 - 6629 View in Reaxys

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α-methyl-α'-phenyl-ethylene oxide Rx-ID: 6046442 View in Reaxys 308/502 Yield

Conditions & References With sulfuric acid Levy; Gombinska; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 713 View in Reaxys McKenzie; Luis; Mitchell; Chemische Berichte; vol. 65; (1932); p. 798,803 View in Reaxys With zinc(II) chloride Levy; Gombinska; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 713 View in Reaxys McKenzie; Luis; Mitchell; Chemische Berichte; vol. 65; (1932); p. 798,803 View in Reaxys

Cp2TiC5H20

Rx-ID: 8449614 View in Reaxys 309/502 Yield

Conditions & References Yield given. Multistep reaction Stille,J.R.; Grubbs,R.H.; Journal of the American Chemical Society; vol. 105; (1983); p. 1664 View in Reaxys

H O

N N

Rx-ID: 37544167 View in Reaxys 310/502 Yield

Conditions & References Reaction Steps: 2 1: chloroform / 8 h / |Inert atmosphere; |Photolysis 2: oxygen; tribromo methane / 15 h / |Photolysis With tribromo methane, oxygen in chloroform Zhang, Xiaoming; Sarkar, Sujan K.; Weragoda, Geethika K.; Rajam, Sridhar; Ault, Bruce S.; Gudmundsdottir, Anna D.; Journal of Organic Chemistry; vol. 79; nb. 2; (2014); p. 653 - 663 View in Reaxys I

N N

Rx-ID: 37544181 View in Reaxys 311/502 Yield

Conditions & References Reaction Steps: 3 1: potassium tert-butylate / diethyl ether / 4 h / 0 °C / |Cooling with ice 2: chloroform / 8 h / |Inert atmosphere; |Photolysis 3: oxygen; tribromo methane / 15 h / |Photolysis With tribromo methane, potassium tert-butylate, oxygen in diethyl ether, chloroform

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Zhang, Xiaoming; Sarkar, Sujan K.; Weragoda, Geethika K.; Rajam, Sridhar; Ault, Bruce S.; Gudmundsdottir, Anna D.; Journal of Organic Chemistry; vol. 79; nb. 2; (2014); p. 653 - 663 View in Reaxys

Br E

Rx-ID: 37544189 View in Reaxys 312/502 Yield

Conditions & References Reaction Steps: 4 1: sodium azide; sodium iodide; ammonium cerium (IV) nitrate / formic acid / 0 °C / |Photolysis 2: potassium tert-butylate / diethyl ether / 4 h / 0 °C / |Cooling with ice 3: chloroform / 8 h / |Inert atmosphere; |Photolysis 4: oxygen; tribromo methane / 15 h / |Photolysis With sodium azide, ammonium cerium (IV) nitrate, tribromo methane, potassium tert-butylate, oxygen, sodium iodide in formic acid, diethyl ether, chloroform Zhang, Xiaoming; Sarkar, Sujan K.; Weragoda, Geethika K.; Rajam, Sridhar; Ault, Bruce S.; Gudmundsdottir, Anna D.; Journal of Organic Chemistry; vol. 79; nb. 2; (2014); p. 653 - 663 View in Reaxys

O N

O H

Rx-ID: 38266826 View in Reaxys 313/502 Yield

Conditions & References Reaction Steps: 2 1: N-butylamine; acetic acid / 60 °C / |Sonication 2: (R,R)-Ph-BPE; hydrogen; bis(norbornadiene)rhodium(I) tetrafluoroborate / dichloromethane / 24 h / 50 °C / 60804.1 Torr / |Autoclave With bis(norbornadiene)rhodium(I) tetrafluoroborate, hydrogen, acetic acid, N-butylamine, (R,R)-Ph-BPE in dichloromethane, 1: |Henry Nitro Aldol Condensation Li, Shengkun; Huang, Kexuan; Zhang, Xumu; Chemical Communications; vol. 50; nb. 64; (2014); p. 8878 - 8881 View in Reaxys

Rx-ID: 40177684 View in Reaxys 314/502 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

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O S

Rx-ID: 1756419 View in Reaxys 315/502 Yield

Conditions & References With methyltriphenylphosphonium tribromide, water, 1.) THF, 3 h, room temperature; further reagents, solvents and times, Yield given. Multistep reaction Cristau, Henri-Jean; Bazbouz, Akram; Morand, Philippe; Torreilles, Eliane; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 2965 - 2966 View in Reaxys

Rx-ID: 1763823 View in Reaxys 316/502 Yield

Conditions & References With HgO*HBF4 in tetrahydrofuran, Time= 4h, T= 70 °C , Yield given. Yields of byproduct given Barluenga, Jose; Alonso-Cires, Luisa; Campos, Pedro J.; Asensio, Gregorio; Tetrahedron; vol. 40; nb. 13; (1984); p. 2563 - 2568 View in Reaxys With HgO*HBF4, Time= 4h, T= 70 °C , reactions of other alkenes with different alcohols and water were also investigated, Mechanism Barluenga, Jose; Alonso-Cires, Luisa; Campos, Pedro J.; Asensio, Gregorio; Tetrahedron; vol. 40; nb. 13; (1984); p. 2563 - 2568 View in Reaxys With HgO*HBF4, Time= 4h, T= 70 °C , Yield given. Yields of byproduct given Barluenga, Jose; Alonso-Cires, Luisa; Campos, Pedro J.; Asensio, Gregorio; Tetrahedron; vol. 40; nb. 13; (1984); p. 2563 - 2568 View in Reaxys O O

Rx-ID: 2340690 View in Reaxys 317/502 Yield

Conditions & References With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 7h, T= 140 °C , Equilibrium constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys With potassium hydroxide, Ru(O2CCF3)2(CO)(PPh3)2, Time= 24h, T= 140 °C , ΔG (gas), Equilibrium constant, Thermodynamic data Strohmeier, Walter; Graser, Barbara; Zeitschrift fuer Physikalische Chemie (Muenchen, Germany); vol. 121; (1980); p. 121 - 130 View in Reaxys With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 24h, T= 140 °C , variat. KOH concentration, Equilibrium constant, Rate constant

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Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys

Rx-ID: 2360060 View in Reaxys 318/502 Yield

Conditions & References

71 %, 2 %, With tetraethylammonium p-toluenesulfonate in N,N-dimethyl-formamide, Ambient temperature, other benzyl chlorides 5% and with propionic anhydride Nishiguchi, Ikuzo; Oki, Tsuneo; Hirashima, Tsuneaki; Shiokawa, Jiro; Chemistry Letters; (1991); p. 2005 - 2008 View in Reaxys 2 %, 5 %, 71 %

With tetraethylammonium p-toluenesulfonate in N,N-dimethyl-formamide, Ambient temperature, electroreduction: Pbcathode, carbon-rod anode, 15mA/cm-2 Nishiguchi, Ikuzo; Oki, Tsuneo; Hirashima, Tsuneaki; Shiokawa, Jiro; Chemistry Letters; (1991); p. 2005 - 2008 View in Reaxys

O (v1)

Rx-ID: 3676753 View in Reaxys 319/502 Yield

Conditions & References in tetrachloromethane, T= 25 °C , var. solvents and temp., other benzyl methyl substituted-benzyl carbinoxy radicals, Mechanism Kim, Sung Soo; Kim, Hong Rae; Kim, Hong Bae; Youn, Sang Jun; Kim, Chul Jae; Journal of the American Chemical Society; vol. 116; nb. 7; (1994); p. 2754 - 2758 View in Reaxys

benzoylacetonediazo anhydride Rx-ID: 6046452 View in Reaxys 320/502 Yield

Conditions & References With water Schroeter; Chemische Berichte; vol. 42; (1909); p. 2346; Chem. Zentralbl.; vol. 81; nb. I; (1910); p. 1470 View in Reaxys Wolff; Justus Liebigs Annalen der Chemie; vol. 325; (1902); p. 137; Justus Liebigs Annalen der Chemie; vol. 394; (1912); p. 46 Anm. 2 View in Reaxys

2H 2H

Rx-ID: 8815234 View in Reaxys 321/502 Yield

Conditions & References With 3,3-dimethyldioxirane in acetone, T= 0 °C , Kinetics Angelis, Yiannis S.; Hatzakis, Nikos S.; Smonou, Ioulia; Orfanopoulos, Michael; Tetrahedron Letters; vol. 42; nb. 22; (2001); p. 3753 - 3756 View in Reaxys

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O O

Rx-ID: 21536881 View in Reaxys 322/502 Yield

Conditions & References Reaction Steps: 2 1: 72 percent / Pd(PPh3)4 With tetrakis(triphenylphosphine) palladium(0) Sato, Mitsuyoshi; Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Tetrahedron Letters; vol. 22; nb. 17; (1981); p. 1609 - 1612 View in Reaxys

Rx-ID: 21566910 View in Reaxys 323/502 Yield

Conditions & References Reaction Steps: 2 1: 1.) Br2 2.) NaOH / 1.) CCl4, 0 deg C 2.) 20 deg C, 5 min. 2: 1.) MCPBA 2.) aq. HCl / 1.) 20 to 25 deg C, 1h With hydrogenchloride, sodium hydroxide, bromine, 3-chloro-benzenecarboperoxoic acid Uemura, Sakae; Fukuzawa, Shin-ichi; Tetrahedron Letters; vol. 24; nb. 40; (1983); p. 4347 - 4350 View in Reaxys

Rx-ID: 638839 View in Reaxys 324/502 Yield

Conditions & References T= 335 °C , Ueberleiten ueber Yttriumoxyd Fourneau; Kanao; Bulletin de la Societe Chimique de France; vol. <4> 35; (1924); p. 620 View in Reaxys With thorium(IV) dioxide, T= 430 - 450 °C Herbst; Manske; Organic Syntheses; vol. 16; (1936); p. 47 View in Reaxys T= 300 - 350 °C , beim Leiten ueber einen Magnesiumoxid-Katalysator Patent; Food Machin. and Chem. Corp.; US2612524; (1948) View in Reaxys T= 420 °C , beim Leiten ueber einen Manganoxid-Katalysator Potapow; Terentew; Zhurnal Obshchei Khimii; vol. 28; (1958); p. 3323,3325 Anm.; J. Gen. Chem. USSR (Engl. Transl.); vol. 28; (1958); p. 3349,3351 Anm. View in Reaxys With yttrium(III) oxide, T= 335 °C Fourneau; Kanao; Bulletin de la Societe Chimique de France; vol. <4> 35; (1924); p. 620 View in Reaxys

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Te H

Rx-ID: 1589069 View in Reaxys 325/502 Yield

Conditions & References With hydrogenchloride, 3-chloro-benzenecarboperoxoic acid, 1.) 20 to 25 deg C, 1h, Yield given. Multistep reaction Uemura, Sakae; Fukuzawa, Shin-ichi; Tetrahedron Letters; vol. 24; nb. 40; (1983); p. 4347 - 4350 View in Reaxys Li

O B

Rx-ID: 2393453 View in Reaxys 326/502 Yield

Conditions & References With N-chloro-succinimide, dimethylsulfide, triethylamine, 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 3.) THF, -78 deg C, 1 h, then room t. 18 h, Yield given. Multistep reaction Pelter, Andrew; Smith, Keith; Elgendy, Said M. A.; Rowlands, Martin; Tetrahedron; vol. 49; nb. 32; (1993); p. 7104 - 7118 View in Reaxys

Rx-ID: 2697384 View in Reaxys 327/502 Yield

Conditions & References With magnesium, 1.) benzene, ether, room temperature, Yield given. Multistep reaction Canonne, Persephone; Foscolos, George B.; Lemay, Gilles; Tetrahedron Letters; vol. 21; (1980); p. 155 - 158 View in Reaxys

Rx-ID: 2925862 View in Reaxys 328/502 Yield

Conditions & References With copper(l) iodide, 1.) ether, 0 deg C, 2.) ether, 0 deg C, 5 h then rt, 4 h, Yield given. Multistep reaction Sakurai, Hideki; Shirahata, Akihiko; Araki, Yoshitaka; Hosomi, Akira; Tetrahedron Letters; vol. 21; nb. 24; (1980); p. 2325 - 2328 View in Reaxys

Cl –

Rx-ID: 3156916 View in Reaxys 329/502 Yield

Conditions & References in gas, T= 148 °C , p= 0 - 0.2Torr , Equilibrium constant French, M. A.; Ikuta, S.; Kebarle, P.; Canadian Journal of Chemistry; vol. 60; (1982); p. 1907 - 1918 View in Reaxys

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Rx-ID: 3758646 View in Reaxys 330/502 Yield

Conditions & References With cobalt-salen complex, sodium, 1.) THF, -70 deg C, 3 h --> r.t. in 2 h; 2.) THF, ether, 3 h, Yield given. Multistep reaction Tabushi, Iawo; Seto, Kiyotomo; Kobuke, Yoshiaki; Tetrahedron; vol. 37; (1981); p. 863 - 865 View in Reaxys

Rx-ID: 5200576 View in Reaxys 331/502 Yield 80 % Spectr.

Conditions & References 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

α-phenyl-acetoacetic acid ester Rx-ID: 6046444 View in Reaxys 332/502 Yield

Conditions & References With sulfuric acid Beckh; Chemische Berichte; vol. 31; (1898); p. 3163 View in Reaxys

(+-)-2-phenyl-propionaldehyde-semicarba‐ zone

Rx-ID: 6046445 View in Reaxys 333/502 Yield

Conditions & References With sulfuric acid Danilow; Zhurnal Obshchei Khimii; vol. 18; (1948); p. 2000,2006; ; (1949); p. 4632 View in Reaxys

etheric solution of benzyl magnesium chloride Rx-ID: 6046459 View in Reaxys 334/502 Yield

Conditions & References With cadmium (II) chloride, anschliessend Behandeln mit Acetylchlorid in Aether unter Kuehlung 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

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phenacetyl-malonic acid ester Rx-ID: 6046462 View in Reaxys 335/502 Yield

Conditions & References With hydrogenchloride Metzner; Justus Liebigs Annalen der Chemie; vol. 298; (1897); p. 379 View in Reaxys

O I OH

Rx-ID: 457016 View in Reaxys 336/502 Yield

Conditions & References With diethyl ether, silver nitrate Porcher; Bulletin de la Societe Chimique de France; vol. <4> 31; (1922); p. 339 View in Reaxys

O O–

Na +

Rx-ID: 588435 View in Reaxys 337/502 Yield

Conditions & References With isopropylmagnesium chloride, anschliessend Erwaermen mit Acetylchlorid und Behandeln des Reaktionsgemisches mit wss. HCl oder wss. H2SO4 Ivanoff; Mihova; Christova; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1321,1324 View in Reaxys

Rx-ID: 665086 View in Reaxys 338/502 Yield

Conditions & References With methyl-magnesium iodide, diethyl ether, benzene Ando; Yuki Gosei Kagaku Kyokaishi; vol. 17; (1959); p. 777,779; ; (1960); p. 4492 View in Reaxys

N H 2N

Rx-ID: 786071 View in Reaxys 339/502 Yield

Conditions & References With ethanol, nickel, Hydrogenation Rupe; Metzger; Vogler; Helvetica Chimica Acta; vol. 8; (1925); p. 850 View in Reaxys

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Rx-ID: 1779487 View in Reaxys 340/502 Yield

Conditions & References Time= 3h, T= 200 - 220 °C , Yield given Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953 View in Reaxys

HO HO

racemate

Rx-ID: 2005273 View in Reaxys 341/502 Yield

Conditions & References

38.7 %, 6.3 With 2,2'-azo-bisisobutyronitrile, oxygen, chlorobenzene, T= 80 °C , p= 759.8Torr , other temperature, Product distri%, 1.8 %, bution, Mechanism 33.1 %, 3.5 Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 %, 2.1 % View in Reaxys

Rx-ID: 2225805 View in Reaxys 342/502 Yield

Conditions & References With hydrogenchloride, Time= 4h, Heating, Yield given Desai, Dhanaji G.; Mane, Ramachandra B.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 20; nb. 6; (1981); p. 504 - 505 View in Reaxys O

O S

Rx-ID: 2575679 View in Reaxys 343/502 Yield

Conditions & References With hydrogenchloride in methanol, Time= 2h, Heating, Yield given Ogura, Katsuyuki; Ohtsuki, Kazuo; Nakamura, Masami; Yahata, Nobuhiro; Takahashi, Kazumasa; Iida, Hirotada; Tetrahedron Letters; vol. 26; nb. 20; (1985); p. 2455 - 2458 View in Reaxys With hydrogenchloride in methanol, Heating, Yield given Ogura, Katsuyuki; Ohtsuki, Kazuo; Takahashi, Kazumasa; Iida, Hirotada; Chemistry Letters; (1986); p. 1597 1598 View in Reaxys With different reagents and reaction times in methanol, Heating, Product distribution

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Ogura, Katsuyuki; Ohtsuki, Kazuo; Nakamura, Masami; Yahata, Nobuhiro; Takahashi, Kazumasa; Iida, Hirotada; Tetrahedron Letters; vol. 26; nb. 20; (1985); p. 2455 - 2458 View in Reaxys 13

CH 3

O S

13CH

Rx-ID: 3091265 View in Reaxys 344/502 Yield

Conditions & References With copper(II) nitrate, Time= 20h, Ambient temperature Broan, Christopher J.; Butler, Anthony R.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 1; (1992); p. 23 - 28 View in Reaxys O

S S

Rx-ID: 3578323 View in Reaxys 345/502 Yield

Conditions & References T= 130 °C Wladislaw, B.; Marzorati, L.; Uchoa, R. B.; Phosphorus and Sulfur and the Related Elements; vol. 32; (1987); p. 87 - 90 View in Reaxys

O S

Rx-ID: 4069817 View in Reaxys 346/502 Yield

Conditions & References With sulfuryl dichloride, triethylamine, 1) CH2Cl2, CCl4, -10 deg C, 3 h, 2a) CH2Cl2, up to r.t., 2b) reflux, 2 h, Yield given. Multistep reaction. Yields of byproduct given Nevalainen, Vesa; Pohjala, Esko; Journal of Chemical Research, Miniprint; nb. 6; (1988); p. 1401 - 1421 View in Reaxys With sulfuryl dichloride, triethylamine, 1) CH2Cl2, CCl4, -10 deg C, 3 h, 2a) CH2Cl2, up to r.t., 2b) reflux, 2 h, Yield given. Multistep reaction. Yields of byproduct given Nevalainen, Vesa; Pohjala, Esko; Journal of Chemical Research, Miniprint; nb. 6; (1988); p. 1401 - 1421 View in Reaxys

(1RS,2SR)-1-phenyl-2-piperidino-propan-1-ol hydrochloride

N O

Rx-ID: 5698710 View in Reaxys 347/502 Yield

Conditions & References With perchloric acid, unter vermindertem Druck

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Takamatsu; Yakugaku Zasshi; vol. 76; (1956); p. 1241; ; (1957); p. 4306 View in Reaxys

(+)(rel-1-R,2S)-1-phenyl-2-piperidino-propan-1-ol

(-)-enantiomer

Rx-ID: 8425748 View in Reaxys 348/502 Yield

Conditions & References With perchloric acid, unter vermindertem Druck Takamatsu; Yakugaku Zasshi; vol. 76; (1956); p. 1241; ; (1957); p. 4306 View in Reaxys

Rx-ID: 11712332 View in Reaxys 349/502 Yield

Conditions & References Reaction Steps: 2 1: aq.NaOH / 3 h / 75 - 80 °C 2: 3 h / 200 - 220 °C With sodium hydroxide Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953 View in Reaxys

O S O S

Rx-ID: 19129467 View in Reaxys 350/502 Yield

Conditions & References Reaction Steps: 2 1: 1.) 60percent sodium hydride / 1.) DMSO, mineral oil 2: 130 °C With sodium hydride Wladislaw, B.; Marzorati, L.; Uchoa, R. B.; Phosphorus and Sulfur and the Related Elements; vol. 32; (1987); p. 87 - 90 View in Reaxys

O 13CH

Rx-ID: 20291939 View in Reaxys 351/502 Yield

Conditions & References Reaction Steps: 2

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1: 1.) BuLi / 1.) THF, hexane, -30 deg C, 30 min, 2.) THF, hexane, RT, overnight 2: claycop / 20 h / Ambient temperature With n-butyllithium, copper(II) nitrate Broan, Christopher J.; Butler, Anthony R.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 1; (1992); p. 23 - 28 View in Reaxys

<2.4-dioxy-phenyl>-benzyl ke‐ tone Rx-ID: 20663088 View in Reaxys 352/502

Yield

Conditions & References Reaction Steps: 2 1: triethylamine / 2 h / 20 - 25 °C 2: 100 percent Chromat. / MCPBA / 1 h / 25 °C With triethylamine, 3-chloro-benzenecarboperoxoic acid Uemura, Sakae; Fukuzawa, Shin-ichi; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1985); p. 471 - 480 View in Reaxys

O O

Rx-ID: 22167104 View in Reaxys 353/502 Yield

Conditions & References Reaction Steps: 2 1: sodium / 0 °C 2: KOH-solution With potassium hydroxide, sodium Morgan; Drew; Porter; Chemische Berichte; vol. 58; (1925); p. 338 View in Reaxys

F O

F O O

O F

F O

F F

Rx-ID: 25991607 View in Reaxys 354/502 Yield

Conditions & References in dichloromethane, Time= 0.25h, Title compound not separated from byproducts. Tellitu, Imanol; Dominguez, Esther; Tetrahedron; vol. 64; nb. 10; (2008); p. 2465 - 2470 View in Reaxys

O O

H N Si

Rx-ID: 32605798 View in Reaxys 355/502 Yield

Conditions & References in dimethylsulfoxide-d6, T= 25 °C , Equilibrium constant

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Sanchez, Dani; Bastida, David; Bures, Jordi; Isart, Carles; Pineda, Oriol; Vilarrasa, Jaume; Organic Letters; vol. 14; nb. 2; (2012); p. 536 - 539 View in Reaxys

Rx-ID: 39559526 View in Reaxys 356/502 Yield

Conditions & References Stage 1: With iodo-alcohol Stage 2: With Oxonereg; Zhu, Min; Zhao, Yang; Chinese Chemical Letters; vol. 26; nb. 2; (2015); p. 248 - 250 View in Reaxys O

Rx-ID: 281820 View in Reaxys 357/502 Yield

Conditions & References With water, sodium sulfite v. Wacek; Kratzl; v. Bezard; Chemische Berichte; vol. 75; (1942); p. 1348,1354 View in Reaxys

O I O

Rx-ID: 457014 View in Reaxys 358/502 Yield

Conditions & References With diethyl ether, silver nitrate, weiteres Nebenprod.: Benzylaethylenglykol Porcher; Bulletin de la Societe Chimique de France; vol. <4> 31; (1922); p. 339 View in Reaxys

O O

Rx-ID: 461767 View in Reaxys 359/502 Yield

Conditions & References With potassium hydroxide Morgan; Drew; Porter; Chemische Berichte; vol. 58; (1925); p. 338 View in Reaxys

O Br–+Mg

O Cl

Rx-ID: 699214 View in Reaxys 360/502 Yield

Conditions & References With diethyl ether, man erhitzt die entstandene Magnesiumverbindung auf 130-140grad und zersetzt das Reaktionsprodukt durch verd. Schwefelsaeure Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 989; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 180,367

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View in Reaxys

Cl (v2)

Rx-ID: 781757 View in Reaxys 361/502 Yield

Conditions & References With acetic acid ester, toluene Morgan; Drew; Porter; Chemische Berichte; vol. 58; (1925); p. 338 View in Reaxys

OH O

O O

Rx-ID: 850178 View in Reaxys 362/502 Yield

Conditions & References With lead(IV) acetate, acetic acid Hock; Kropf; Chemische Berichte; vol. 91; (1958); p. 1681,1682, 1686 View in Reaxys

O+

O– O

Cl OO

Rx-ID: 1672169 View in Reaxys 363/502 Yield

Conditions & References With hydrogenchloride, 1.) ether, Yield given. Multistep reaction Mezheritskaya, L. V.; Matsovskaya, E. S.; Dorofeenko, G. N.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 174 - 178; Zhurnal Organicheskoi Khimii; vol. 16; nb. 1; (1980); p. 183 - 188 View in Reaxys

C– H

Rx-ID: 1793080 View in Reaxys 364/502 Yield 88 %

Conditions & References Time= 1h, Irradiation Fox, Marye Anne; Younathan, Janet; Fryxell, Glen E.; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 3109 - 3112 View in Reaxys

88 %

Time= 1h, Irradiation, var. aryl halide, var. irradiat. time when filtered, var. wavelength, Mechanism, Quantum yield Fox, Marye Anne; Younathan, Janet; Fryxell, Glen E.; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 3109 - 3112 View in Reaxys

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O O

Rx-ID: 2005259 View in Reaxys 365/502 Yield

Conditions & References With iodosylbenzene, Mn salen complex 2 in acetonitrile, Time= 12h, Ambient temperature, Mechanism Irie, Ryo; Noda, Keiko; Ito, Yoshio; Matsumoto, Naohide; Katsuki, Tsutomu; Tetrahedron Letters; vol. 31; nb. 50; (1990); p. 7345 - 7348 View in Reaxys

Rx-ID: 2038378 View in Reaxys 366/502 Yield

Conditions & References With water, β-diketone hydrolase, Time= 15h, T= 30 °C , in phosphate buffer at pH 7.0; substrate specifity of catalyst, Product distribution Sakai, Kiyofumi; Hamada, Nobutake; Watanabe, Yasuto; Agricultural and Biological Chemistry; vol. 50; nb. 4; (1986); p. 989 - 996 View in Reaxys H N

H 2N

Rx-ID: 2103384 View in Reaxys 367/502 Yield

Conditions & References With hydrogenchloride in methanol, water, T= 20.6 °C , pH 1.5, Rate constant Zielinski, Wojciech; Polish Journal of Chemistry; vol. 54; nb. 4; (1980); p. 745 - 754 View in Reaxys

O N

Rx-ID: 2677946 View in Reaxys 368/502 Yield

Conditions & References With hydrogenchloride, iron, Yield given. Multistep reaction Kumari, L. Krishna; Pardhasaradhi, M.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 21; nb. 12; (1982); p. 1067 - 1070 View in Reaxys

O O

Rx-ID: 2794765 View in Reaxys 369/502 Yield

Conditions & References With sulfuric acid, water in 1,4-dioxane, T= 25 °C , Equilibrium constant Antonovskii, V. L.; Fedorova, E. V.; Shtivel', N. E.; Emelin, Yu. D.; Journal of Organic Chemistry USSR (English Translation); vol. 27; nb. 4; (1991); p. 704 - 706; Zhurnal Organicheskoi Khimii; vol. 27; nb. 4; (1991); p. 820 - 823 View in Reaxys

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H 2N

Rx-ID: 2950953 View in Reaxys 370/502 Yield

Conditions & References With monoamineoxidase from rat liver mitochondria, phosphate-buffer in water, Time= 1h, T= 37 °C , biotransformation studies, metabolism, the enzyme activity; other enzymes: ketoreductase; aerobic and anaerobic incubations; various cosubstrates Blume; Arzneimittel-Forschung/Drug Research; vol. 31; nb. 6; (1981); p. 994 - 997 View in Reaxys

H 2N

Rx-ID: 2950954 View in Reaxys 371/502 Yield

Conditions & References With G6P, glucose-6-phosphat-degydrogenase, rat liver mitochondria enzyme, NADP, magnesium chloride in water, Time= 1h, T= 37 °C , relative activity, Rate constant Blume; Arzneimittel-Forschung/Drug Research; vol. 31; nb. 5; (1981); p. 805 - 809 View in Reaxys

O N H

H 2N O

Rx-ID: 3601938 View in Reaxys 372/502 Yield

HO racemate

Rx-ID: 3609015 View in Reaxys 373/502 Yield

Conditions & References With N,N,N',N',N'',N''-hexamethylphosphoric triamide, potassium hydride, ammonium chloride, 1.) 30 deg C, 24 h; 2.) water, 0 deg C, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Snowden, Roger L.; Helvetica Chimica Acta; vol. 66; nb. 4; (1983); p. 1031 - 1038 View in Reaxys

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O S

N N O

Rx-ID: 3910784 View in Reaxys 374/502 Yield

Conditions & References With tert.-butyl lithium, 1) THF, 10 deg C, 5 min, 2) THF, -78 deg C to r.t., Yield given. Multistep reaction Baldwin, Jack E.; Bottaro, Jeffrey C.; Journal of the Chemical Society, Chemical Communications; nb. 21; (1981); p. 1121 - 1122 View in Reaxys

F O

HO racemate

racemate

Rx-ID: 4114204 View in Reaxys 375/502 Yield

Conditions & References

80 % With KH2F3 in 1,2-dichloro-ethane, Time= 12h, T= 80 °C , further epoxides, Product distribution Spectr., 20 % Spectr. Tamura, Masanori; Shibakami, Motonari; Arimura, Takashi; Kurosawa, Shigeru; Sekiya, Akira; Journal of Fluorine Chemistry; vol. 70; nb. 1; (1995); p. 1 - 4 View in Reaxys

O Mg Cl

Na +

O–

Rx-ID: 533468 View in Reaxys 376/502 Yield

Conditions & References With diethyl ether, anschliessendes Erwaermen mit Acetylchlorid Ivanoff; Mihova; Christova; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1321,1324 View in Reaxys

Rx-ID: 37544175 View in Reaxys 377/502 Yield 10 %Chromat., 9 %Chromat., 81 %Chromat.

Conditions & References With tribromo methane, oxygen, Time= 15h, Photolysis Zhang, Xiaoming; Sarkar, Sujan K.; Weragoda, Geethika K.; Rajam, Sridhar; Ault, Bruce S.; Gudmundsdottir, Anna D.; Journal of Organic Chemistry; vol. 79; nb. 2; (2014); p. 653 - 663 View in Reaxys

O O

Rx-ID: 1548755 View in Reaxys 378/502

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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 Bio-Organic Chemistry (1972-1999); (1980); p. 1098 - 1103 View in Reaxys

Rx-ID: 2152448 View in Reaxys 379/502 Yield

Conditions & References Yield given Sato, Mitsuyoshi; Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Tetrahedron Letters; vol. 22; nb. 17; (1981); p. 1609 - 1612 View in Reaxys

O O Si

Rx-ID: 2177078 View in Reaxys 380/502 Yield

Conditions & References

11 % Chromat., 13 % Chromat., 4 % Chromat., 13 % Chromat.

in benzene, Time= 4h, Ambient temperature, Irradiation, product yield distribution after hydrolysis, Product distribution Kira, Mitsuo; Yoshida, Hitoaki; Sakurai, Hideki; Journal of the American Chemical Society; vol. 107; nb. 25; (1985); p. 7767 - 7768 View in Reaxys

Rx-ID: 3525013 View in Reaxys 381/502 Yield

Conditions & References With potassium tert-butylate in dimethyl sulfoxide, multistep reaction: other ketones and t-butyl sulfides, Product distribution, Mechanism Dell'Erba, Carlo; Novi, Marino; Petrillo, Giovanni; Tavani, Cinzia; Tetrahedron; vol. 48; nb. 2; (1992); p. 325 - 334 View in Reaxys With potassium tert-butylate, 1) DMSO, 2) RT, 100 min, Yield given. Multistep reaction Dell'Erba, Carlo; Novi, Marino; Petrillo, Giovanni; Tavani, Cinzia; Tetrahedron; vol. 48; nb. 2; (1992); p. 325 - 334 View in Reaxys

O Si

Rx-ID: 3609467 View in Reaxys 382/502

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Yield

Conditions & References

11 %, 13 Irradiation %, 4 %, 13 Sakurai, Hideki; Phosphorus and Sulfur and the Related Elements; vol. 27; (1986); p. 205 - 210 % View in Reaxys 11 %, 13 Irradiation %, 13 %, 4 Sakurai, Hideki; Phosphorus and Sulfur and the Related Elements; vol. 27; (1986); p. 205 - 210 % View in Reaxys 13 %, 4 %, Irradiation 13 %, 11 % Sakurai, Hideki; Phosphorus and Sulfur and the Related Elements; vol. 27; (1986); p. 205 - 210 View in Reaxys 11 %, 4 %, Irradiation 13 %, 13 % Sakurai, Hideki; Phosphorus and Sulfur and the Related Elements; vol. 27; (1986); p. 205 - 210 View in Reaxys

–O

calciumphenyl acetate

Ca 2+

Rx-ID: 6046455 View in Reaxys 383/502 Yield

Conditions & References durch trockne Destillation Apitzsch; Chemische Berichte; vol. 38; (1905); p. 2895 View in Reaxys Hill; Hale; American Chemical Journal; vol. 33; (1905); p. 10 View in Reaxys Ludlam; Journal of the Chemical Society; vol. 81; (1902); p. 1189 View in Reaxys

Rx-ID: 10302194 View in Reaxys 384/502 Yield

Conditions & References With 1-methyl-1H-imidazole, Time= 50h, T= 20 °C , Dakin-West reaction, Kinetics, Further Variations: Reagents Tran, Khanh-Van; Bickar, David; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6640 - 6643 View in Reaxys

–O

Na +

Rx-ID: 555263 View in Reaxys 385/502 Yield

Conditions & References 40-stdg. Erhitzen auf Siedetemperatur Stoermer; Stroh; Chemische Berichte; vol. 68; (1935); p. 2112,2116 View in Reaxys 18-stdg. Erhitzen auf Siedetemperatur King; McMillan; Journal of the American Chemical Society; vol. 68; (1946); p. 525 View in Reaxys Magidson; Garkuscha; Zhurnal Obshchei Khimii; vol. 11; (1941); p. 339,341; ; (1941); p. 5868

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View in Reaxys

H N

O O

N O

O O

Rx-ID: 1704042 View in Reaxys 386/502 Yield

Conditions & References

24.3 % Chromat., 55.5 % Chromat., 4.1 % Chromat., 8.5 % Chromat., 2.9 % Chromat.

With oxygen in ethyl acetate, T= 50 °C , further use of different solvent (CH3CN), 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

H Z

O racemate

racemate

Rx-ID: 2005275 View in Reaxys 387/502 Yield

Conditions & References

18 %, 15 %, 8.4 %, 8.0 %, 3.2 %

O O

C–

Rx-ID: 2450825 View in Reaxys 388/502 Yield

Conditions & References With 2,6-di-tert-butyl-pyridine in ethanol, Time= 15h, 0.11 M 2,6-di-tert-butylpyridine/0.03 M TosOH buffer, Yield given Luening, Ulrich; Schillinger, Fritz; Chemische Berichte; vol. 123; nb. 10; (1990); p. 2073 - 2075 View in Reaxys With protonated concave pyridine 8*H+ in ethanol, Time= 15h, 0.11 M concave pyridine 8/0.03 M TosOH buffer; other proton sources, other sec. nitronate anions, Product distribution Luening, Ulrich; Schillinger, Fritz; Chemische Berichte; vol. 123; nb. 10; (1990); p. 2073 - 2075 View in Reaxys

Cl O

Rx-ID: 3317757 View in Reaxys 389/502 Yield

Conditions & References

15 % Chro- With aluminum tri-bromide mat., 20 % Chromat.,

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1 % Chromat., 30 % Chromat.

Rozenberg, V. I.; Nikanorov, V. A.; Reutov, O. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 35; (1986); p. 1911 - 1915; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1986); p. 2097 - 2101 View in Reaxys

methyl-phenyl-ethylene oxide carboxylic acid ethyl ester Rx-ID: 6046460 View in Reaxys 390/502 Yield

Conditions & References Verseifung und Abspaltung von CO2 Darzens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 142; (1906); p. 215 View in Reaxys

methyl-phenyl-ethylene oxide Rx-ID: 6046461 View in Reaxys 391/502 Yield

Conditions & References durch Destillation Fourneau; Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 662; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 140; (1905); p. 1595 View in Reaxys

kieselguhr O

Rx-ID: 8261825 View in Reaxys 392/502 Yield

Conditions & References T= 600 °C , p= 15Torr , (+-)-2-phenyl-propionaldehyde Ramart-Lucas; Salmon-Legagneur; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1069,1083 View in Reaxys Ramart-Lucas; Guerlain; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1860,1867 View in Reaxys

Rx-ID: 2140430 View in Reaxys 393/502 Yield

Conditions & References in benzene-d6, T= 25 °C , other solvent, Equilibrium constant Zielinski, W.; Mazik, M.; Polish Journal of Chemistry; vol. 66; nb. 4; (1992); p. 661 - 668 View in Reaxys

HO O

acetate_of barium Rx-ID: 6046451 View in Reaxys 394/502

Yield

Conditions & References durch trockne Destillation Radziszewski; Chemische Berichte; vol. 3; (1870); p. 198

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View in Reaxys

glass wool

Rx-ID: 7448169 View in Reaxys 395/502 Yield

Conditions & References T= 400 - 450 °C , p= 30Torr Grignard; Chambret; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 302 View in Reaxys

glass wool

Rx-ID: 8261824 View in Reaxys 396/502 Yield

Conditions & References T= 400 °C , p= 30Torr Grignard; Chambret; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 302 View in Reaxys

Cl (v2)

Rx-ID: 781736 View in Reaxys 397/502 Yield

Conditions & References Popow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 4; (1872); p. 216; Chemische Berichte; vol. 5; (1872); p. 501 View in Reaxys

Rx-ID: 818044 View in Reaxys 398/502 Yield

Conditions & References durch Verseifen des Reaktionsproduktes mit methylalkoholischer Kalilauge Barbier; Locquin; Bulletin de la Societe Chimique de France; vol. <4> 9; (1911); p. 720 View in Reaxys

H C– H

O P O–

O O

P O

Rx-ID: 1793079 View in Reaxys 399/502 Yield

Conditions & References in ammonia, T= -33 °C , Irradiation, competitive reaction, at known concentrations; relative rate constants, half life, Product distribution Bunnett, Joseph F.; Mitchel, Eric; Galli, Carlo; Tetrahedron; vol. 41; nb. 19; (1985); p. 4119 - 4132 View in Reaxys

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O O

Rx-ID: 2141899 View in Reaxys 400/502 Yield

Conditions & References With (tBuOOCO)2, Time= 32h, T= 35 °C , sealed evacuated tube, other temperature, Product distribution, Mechanism Dodonov, V.A.; Zaburdyaeva, S.N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 47 - 49; Zhurnal Organicheskoi Khimii; vol. 22; nb. 1; (1986); p. 56 - 58 View in Reaxys

Rx-ID: 2409536 View in Reaxys 401/502 Yield

Conditions & References ester condensation Dommroese, Anne-Marie; Gruetzmacher, Hans-Friedrich; Organic Mass Spectrometry; vol. 22; (1987); p. 437 443 View in Reaxys

Rx-ID: 3382701 View in Reaxys 402/502 Yield

Conditions & References With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 35h, T= 140 °C , Equilibrium constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 22h, T= 140 °C , Equilibrium constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys

Rx-ID: 3382715 View in Reaxys 403/502 Yield

Conditions & References Yield given. Multistep reaction Uemura, Sakae; Ohe, Kouichi; Sugita, Nobuyuki; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 6; (1990); p. 1697 - 1703 View in Reaxys

Rx-ID: 3382939 View in Reaxys 404/502 Yield

Conditions & References Yield given. Multistep reaction

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Uemura, Sakae; Ohe, Kouichi; Sugita, Nobuyuki; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 6; (1990); p. 1697 - 1703 View in Reaxys

aqueous methanol. KOH

O N

N O

Rx-ID: 5698706 View in Reaxys 405/502 Yield

Conditions & References Newman; Kutner; Journal of the American Chemical Society; vol. 73; (1951); p. 4199,4202 View in Reaxys

kieselguhr HO

Rx-ID: 7448174 View in Reaxys 406/502 Yield

Conditions & References T= 550 °C , p= 10 - 20Torr Ramart-Lucas; Salmon-Legagneur; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1069,1083 View in Reaxys 2H 2H

H E

O 2H

2H 2H

O O

Z 2H

2H 2H

O 2H 2H

2H 2H

Rx-ID: 33756195 View in Reaxys 407/502 Yield

Conditions & References With [Au(PMe3)SbF6], Time= 4.33333h Roithova, Jana; Jankova, Stepanka; Jasikova, Lucie; Vana, Jiri; Hybelbauerova, Simona; Angewandte Chemie - International Edition; vol. 51; nb. 33; (2012); p. 8378 - 8382 View in Reaxys

–O

K+

Rx-ID: 555260 View in Reaxys 408/502 Yield

Conditions & References Erhitzen auf Siedetemperatur Hurd; Thomas; Journal of the American Chemical Society; vol. 58; (1936); p. 1240 View in Reaxys Hurd; Christ; Thomas; Journal of the American Chemical Society; vol. 55; (1933); p. 2589,2591 View in Reaxys

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Rx-ID: 3738243 View in Reaxys 409/502 Yield

Conditions & References

13 %, 9 %, With Titanium(IV) oxide, silver sulphate, Time= 5h, Ambient temperature, Irradiation, TiO2-photosensitized oxidation 6% Baciocchi, Enrico; Rol, Cesare; Sebastiani, Giovanni V.; Taglieri, Luca; Journal of Organic Chemistry; vol. 59; nb. 18; (1994); p. 5272 - 5276 View in Reaxys H N

O Cl

not aqueous solvent

H 2N

Rx-ID: 8261831 View in Reaxys 410/502 Yield

Conditions & References Herbst; Johnson; Journal of the American Chemical Society; vol. 52; (1930); p. 3676,3679 View in Reaxys

H –

Na +

Rx-ID: 6046449 View in Reaxys 411/502 Yield

Conditions & References Leake; Levine; Journal of the American Chemical Society; vol. 81; (1959); p. 1169,1171 View in Reaxys

O O

Rx-ID: 6715123 View in Reaxys 412/502 Yield

Conditions & References Mechanism Buchanan; Mc Ardle; Journal of the Chemical Society; (1952); p. 2944 View in Reaxys King; McMillan; Journal of the American Chemical Society; vol. 73; (1951); p. 4911,4914 View in Reaxys –O

Hg 2+

O O

Rx-ID: 1548675 View in Reaxys 413/502 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 Bio-Organic Chemistry (1972-1999); (1980); p. 1098 - 1103 View in Reaxys

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T-4

O O T-4

H O

Rx-ID: 1828827 View in Reaxys 414/502 Yield

Conditions & References

in benzene, Time= 72h, T= 150 °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. 651 - 676 View in Reaxys

OH HO

S OO

Rx-ID: 7448164 View in Reaxys 415/502 Yield

Conditions & References T= -15 °C Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys T= 145 °C , (+-)-2-phenyl-propionaldehyde Danilow; Zhurnal Obshchei Khimii; vol. 18; (1948); p. 2000,2006; ; (1949); p. 4632 View in Reaxys

aqueous KOH-solution

Rx-ID: 8261827 View in Reaxys 416/502 Yield

Conditions & References Ivanoff; Mihova; Christova; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1321,1324 View in Reaxys Spassoff; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 275,278 View in Reaxys T= 70 - 85 °C , Rate constant Spassoff; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 275,278 View in Reaxys

O Br–+Mg

O Cl

Rx-ID: 698915 View in Reaxys 417/502 Yield

Conditions & References man erhitzt vor der Zers. mit verd.Schwefelsaeure die gebildete Magnesiumverbindung auf 130-140grad

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Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 989; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 180,367 View in Reaxys T= 130 - 140 °C , anschl. Zersetzen mit verd. H2SO4 Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 989; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 180,367 View in Reaxys Tiffeneau; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 180,367 View in Reaxys

Rx-ID: 2925863 View in Reaxys 418/502 Yield

Conditions & References With copper(l) iodide, 1.) ether, 0 deg C, 2.) ether, 0 deg C, 5.5 h, other reaction time and temperature, Product distribution Sakurai, Hideki; Shirahata, Akihiko; Araki, Yoshitaka; Hosomi, Akira; Tetrahedron Letters; vol. 21; nb. 24; (1980); p. 2325 - 2328 View in Reaxys

H NH

Rx-ID: 3737785 View in Reaxys 419/502 Yield

Conditions & References

2 %, 22 %, With Titanium(IV) oxide, silver sulphate, Time= 5h, Ambient temperature, Irradiation, TiO2-photosensitized oxidation 16 %, 3 %, Baciocchi, Enrico; Rol, Cesare; Sebastiani, Giovanni V.; Taglieri, Luca; Journal of Organic Chemistry; vol. 59; nb. 14 % 18; (1994); p. 5272 - 5276 View in Reaxys

Na +

–N

H N

H 2N

Rx-ID: 6683937 View in Reaxys 420/502 Yield

Conditions & References Leake; Levine; Journal of the American Chemical Society; vol. 81; (1959); p. 1169,1171 View in Reaxys

sodium amalgam

hydrochloride of methyl-<α-methylamino-benzyl>-carbinol

H 2N

Rx-ID: 8277636 View in Reaxys 421/502 Yield

Conditions & References T= 0 °C

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Emde; Runne; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 379 View in Reaxys Schmidt; Chem. Zentralbl.; vol. 82; nb. II; (1911); p. 34 View in Reaxys

Cl H

racemate

Rx-ID: 588061 View in Reaxys 422/502 Yield

Conditions & References T= 230 - 260 °C , unter vermindertem Druck Bodendorf; Dettke; Chemische Berichte; vol. 89; (1956); p. 114 View in Reaxys O O N

Rx-ID: 1580328 View in Reaxys 423/502 Yield

Conditions & References

24.4 %, 2.8 Irradiation, 125 or 250 mM benzophenone as sensitizer, without sensitizer, Product distribution, Mechanism % Tomioka, Hideo; Okuno, Hiroshi; Izawa, Yasuji; Journal of Organic Chemistry; vol. 45; nb. 26; (1980); p. 5278 5283 View in Reaxys

Cl Al

Rx-ID: 5698701 View in Reaxys 424/502 Yield

Conditions & References T= 260 °C Levy; Sfiras; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 184; (1927); p. 1337 View in Reaxys

S OO

Rx-ID: 5698702 View in Reaxys 425/502 Yield

Conditions & References T= -15 °C Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys

yttrium oxide Rx-ID: 6683935 View in Reaxys 426/502

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Yield

Conditions & References T= 335 °C Fourneau; Kanao; Bulletin de la Societe Chimique de France; vol. <4> 35; (1924); p. 620 View in Reaxys

O O

N O

palladium coal

Rx-ID: 7064279 View in Reaxys 427/502 Yield

Conditions & References T= 28 - 36 °C , Hochdruckhydrierung; anschliessendes Erwaermen mit wss. NaOH und Behandlung des Reaktionsgemisches mit wss. H2SO4 Patent; Comm. Solv. Corp.; US2427822; (1945) View in Reaxys

OH OH HO

S OO

Rx-ID: 7448165 View in Reaxys 428/502 Yield

Conditions & References T= -19 °C Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys

O OH

mercury (II)-chloride O

Rx-ID: 7448170 View in Reaxys 429/502 Yield

Conditions & References T= 100 °C , im Rohr Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys O S

O O S

PhSSPh (4percent)

Rx-ID: 8493572 View in Reaxys 430/502 Yield 51 % Chromat., 22 % Chromat., 17 % Chromat., 7 % Chromat.,

Conditions & References in tert-butyl alcohol, Irradiation, photolysis of alkyl aryl sulfoxides; homolytic cleavage; possible reaction pathways; proposed mechanism; thermal degradation (t-BuOH, 80 deg C); comparison of olefinic products from photolysis and thermolysis; regioselectivity of alkene products, Product distribution, Quantum yield Guo, Yushen; Jenks, William S.; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 857 - 864 View in Reaxys

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6 % Chromat., 6 % Chromat.

HN S

H 2N

O racemate

racemate

Rx-ID: 5698708 View in Reaxys 431/502 Yield

Conditions & References T= 160 °C Kojima; Yakugaku Zasshi; vol. 79; (1959); p. 20,22; ; (1959); p. 10186 View in Reaxys

HN O

NH 2

S racemate

racemate

Rx-ID: 5698709 View in Reaxys 432/502 Yield

Conditions & References T= 160 °C Kojima; Yakugaku Zasshi; vol. 79; (1959); p. 20,22; ; (1959); p. 10186 View in Reaxys

HN S

NH 2

S racemate

racemate

Rx-ID: 5698711 View in Reaxys 433/502 Yield

Conditions & References T= 160 °C Kojima; Yakugaku Zasshi; vol. 79; (1959); p. 20,22; ; (1959); p. 10186 View in Reaxys

Rx-ID: 7448172 View in Reaxys 434/502 Yield

Conditions & References T= 80 °C , 2-acetoxy-1-phenyl-propen-(1) of bp 3: 103 degree Boeeseken; Jacobs; Recueil des Travaux Chimiques des Pays-Bas; vol. 55; (1936); p. 786,788 View in Reaxys

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2.5-dimethyl-2.5-diphenyl-1.4-dioxane

S OO

Rx-ID: 7448175 View in Reaxys 435/502 Yield

Conditions & References T= 50 - 55 °C , im Kohlendioxyd-Strom Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys

OH S OO

Na2Cr2O7

Rx-ID: 8261826 View in Reaxys 436/502 Yield

Conditions & References Levene; Walti; Journal of Biological Chemistry; vol. 90; (1931); p. 81,86 View in Reaxys

O N

N H

Rx-ID: 2397705 View in Reaxys 437/502 Yield

Conditions & References Yield given. Multistep reaction Baldwin, Jack E.; Adlington, Robert M.; Bottaro, Jeffrey C.; Kolhe, Jayant N.; Perry, Matthew W. D.; Jain, Ashok U.; Tetrahedron; vol. 42; nb. 15; (1986); p. 4223 - 4234 View in Reaxys reaction with aldehydes, ketones, alkyl halides, crotonates; multistep reactions Baldwin, Jack E.; Adlington, Robert M.; Bottaro, Jeffrey C.; Kolhe, Jayant N.; Perry, Matthew W. D.; Jain, Ashok U.; Tetrahedron; vol. 42; nb. 15; (1986); p. 4223 - 4234 View in Reaxys

OH H 2N 2 O

HO O

Rx-ID: 406420 View in Reaxys 438/502 Yield

Conditions & References Attwood; Stevenson; Thorpe; Journal of the Chemical Society; vol. 123; (1923); p. 1755 - 1766 View in Reaxys Sonn; Litten; Chemische Berichte; vol. 66; (1933); p. 1512,1518 View in Reaxys

H N

NH 2

Rx-ID: 806745 View in Reaxys 439/502 Yield

Conditions & References Levy; Gombinska; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 713 View in Reaxys Levy; Dvoleitzka-Gombinska; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1765,1775

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View in Reaxys

OH N E E N

O Z H 2N

O N H

N H

N O

Rx-ID: 3601636 View in Reaxys 440/502 Yield

Conditions & References With hydrogenchloride, phosphorus pentachloride, multistep reaction, rearrangement and/or hydrolysis products; var. solvents, var. time; var. temp.; also other oxime, Product distribution, Mechanism Zielinski, Wojciech; Polish Journal of Chemistry; vol. 54; nb. 4; (1980); p. 745 - 754 View in Reaxys

OH S OO

Rx-ID: 5698703 View in Reaxys 441/502 Yield

anhydrous zinc chloride

Rx-ID: 5698705 View in Reaxys 442/502 Yield

Conditions & References Levy; Sfiras; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 184; (1927); p. 1337 View in Reaxys

O O

KOH-solution O

<2.4-dioxy-phenyl>-benzyl ke‐ tone

Rx-ID: 5723306 View in Reaxys 443/502 Yield

Conditions & References Hydrolysis Baker; Journal of the Chemical Society; vol. 127; (1925); p. 2354; Journal of the Chemical Society; (1927); p. 2898 View in Reaxys

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N O OH

nickel

α-acetophenylacetaldim

Rx-ID: 6046463 View in Reaxys 444/502 Yield

Conditions & References Rupe; Metzger; Vogler; Helvetica Chimica Acta; vol. 8; (1925); p. 850 View in Reaxys

aqueous Na2SO3-solution

2-oxo-1-phenyl-propane-sulfonic acid-(1) Rx-ID: 7448176 View in Reaxys 445/502 Yield

Conditions & References v. Wacek; Kratzl; v. Bezard; Chemische Berichte; vol. 75; (1942); p. 1348,1354 View in Reaxys

O O

Rx-ID: 640322 View in Reaxys 446/502 Yield

Conditions & References Sonn; Litten; Chemische Berichte; vol. 66; (1933); p. 1512,1518 View in Reaxys

H N

O O

NH 2

Rx-ID: 806752 View in Reaxys 447/502 Yield

Conditions & References McKenzie; Luis; Mitchell; Chemische Berichte; vol. 65; (1932); p. 798,803 View in Reaxys 1

-1 O

C– H

Rx-ID: 4932105 View in Reaxys 448/502 Yield

Conditions & References Rate constant Galli, Carlo; Gentili, Patrizia; Acta Chemica Scandinavica; vol. 52; nb. 1; (1998); p. 67 - 76 View in Reaxys

OH HO

O O

S OO

Rx-ID: 5698704 View in Reaxys 449/502 Yield

Conditions & References McKenzie; Luis; Mitchell; Chemische Berichte; vol. 65; (1932); p. 798,803 View in Reaxys

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KOH-solution

O HO

Rx-ID: 5714669 View in Reaxys 450/502 Yield

Conditions & References Jacobson; Ghosh; Journal of the Chemical Society; vol. 107; (1915); p. 1055 View in Reaxys Baker; Journal of the Chemical Society; vol. 127; (1925); p. 2354; Journal of the Chemical Society; (1927); p. 2898 View in Reaxys

sodium nitrite H 2N

Rx-ID: 7064280 View in Reaxys 451/502 Yield

Conditions & References Tiffeneau; Cahnmann; Bulletin de la Societe Chimique de France; vol. <5> 2; (1935); p. 1876,1881, 1882 View in Reaxys

NH 2 N O

N H

S OO

Rx-ID: 7448166 View in Reaxys 452/502 Yield

Conditions & References Danilow; Zhurnal Obshchei Khimii; vol. 18; (1948); p. 2000,2006; ; (1949); p. 4632 View in Reaxys

OH S OO

Rx-ID: 7448167 View in Reaxys 453/502 Yield

Conditions & References high-melting form Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 142; (1906); p. 1538; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 351 View in Reaxys O

H O

O O

Rx-ID: 7448168 View in Reaxys 454/502 Yield

Conditions & References Metzner; Justus Liebigs Annalen der Chemie; vol. 298; (1897); p. 379 View in Reaxys

PdO

N O

CuO

petroleum ether Rx-ID: 7448171 View in Reaxys 455/502

Yield

Conditions & References weitere Reagenzien: Benzol, Wasserstoff

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Birkofer; Chemische Berichte; vol. 80; (1947); p. 92 View in Reaxys

OH HO

S OO

H HO

OH H

racemate

Rx-ID: 8261822 View in Reaxys 456/502 Yield

Conditions & References Zincke; Zahn; Chemische Berichte; vol. 43; (1910); p. 855 View in Reaxys

O H

H O

O HO

amalgamated aluminium

Rx-ID: 8261823 View in Reaxys 457/502 Yield

Conditions & References Bauer et al.; Chemicke Zvesti; vol. 9; (1955); p. 604; ; (1956); p. 11273 View in Reaxys

KOH-solution

Rx-ID: 8261828 View in Reaxys 458/502 Yield

Conditions & References Hydrolysis Morgan; Drew; Porter; Chemische Berichte; vol. 58; (1925); p. 338 View in Reaxys O

hydrogen chloride containing ethanol

S O

Rx-ID: 8261829 View in Reaxys 459/502 Yield

Conditions & References v.Wacek; Kratzl; ; vol. 20; (1942); p. 108,110 View in Reaxys O HO

Cl –

H N+

sodium amalgam

Rx-ID: 8261830 View in Reaxys 460/502 Yield

Conditions & References Emde; Runne; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 379 View in Reaxys

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sodium amalgam

N H

Rx-ID: 8261832 View in Reaxys 461/502 Yield

Conditions & References Emde; Runne; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 379 View in Reaxys

sodium amalgam

N H

Rx-ID: 8261833 View in Reaxys 462/502 Yield

Conditions & References Emde; Runne; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 379 View in Reaxys

OH O

bis-<1-phenyl-2-piperidino-propyl>-ether

Cl OO

(+)-enantiomer,rel-configuration

Rx-ID: 8491540 View in Reaxys 463/502 Yield

Conditions & References Erwaermen unter vermindertem Druck Takamatsu; Yakugaku Zasshi; vol. 76; (1956); p. 1241; ; (1957); p. 4306 View in Reaxys

–O

Cr 3+

Rx-ID: 339999 View in Reaxys 464/502 Yield

Conditions & References Haller; Ramart; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 174; (1922); p. 1212 View in Reaxys O

O Se

Rx-ID: 1600571 View in Reaxys 465/502 Yield

Conditions & References Time= 6.5h, Heating, also with silica gel, Product distribution Tiecco, Marcello; Testaferri, Lorenzo; Tingoli, Marco; Chianelli, Donatella; Bartoli, Donatella; Gazzetta Chimica Italiana; vol. 117; nb. 7; (1987); p. 423 - 428 View in Reaxys

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nitrogen

H 2N 2

N N

Rx-ID: 5739967 View in Reaxys 466/502 Yield

Conditions & References Wolff; Justus Liebigs Annalen der Chemie; vol. 325; (1902); p. 137; Justus Liebigs Annalen der Chemie; vol. 394; (1912); p. 46 Anm. 2 View in Reaxys

concentrated aqueous silver nitrate

Rx-ID: 7448177 View in Reaxys 467/502 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 188,355 View in Reaxys

yellow mercury oxide

Rx-ID: 7448178 View in Reaxys 468/502 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 188,355 View in Reaxys

OH HO

H N

H 2N

S OO

Rx-ID: 7448179 View in Reaxys 469/502 Yield

Conditions & References Takamatsu; Yakugaku Zasshi; vol. 76; (1956); p. 1241; ; (1957); p. 4306 View in Reaxys

H N

OH HO

P OH O

H 2N

racemate

Rx-ID: 7448180 View in Reaxys 470/502 Yield

Conditions & References Auterhoff; Roth; Archiv der Pharmazie (Weinheim, Germany); vol. 289; (1956); p. 470,474 View in Reaxys

O OH

Rx-ID: 7919794 View in Reaxys 471/502 Yield

Conditions & References Ganellin; Pettit; Journal of the Chemical Society; (1958); p. 576,580 View in Reaxys

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OH HO

H 2N

S OO

Rx-ID: 7919795 View in Reaxys 472/502 Yield

Conditions & References Takamatsu; Yakugaku Zasshi; vol. 76; (1956); p. 1241; ; (1957); p. 4306 View in Reaxys O O

N N

Rx-ID: 7924052 View in Reaxys 473/502 Yield

Conditions & References Wolff; Justus Liebigs Annalen der Chemie; vol. 325; (1902); p. 137; Justus Liebigs Annalen der Chemie; vol. 394; (1912); p. 46 Anm. 2 View in Reaxys

chromic acid O

Rx-ID: 8261834 View in Reaxys 474/502 Yield

Conditions & References Apolit; Annales de Chimie (Cachan, France); vol. <10> 2; (1924); p. 73; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 172; (1921); p. 1495 View in Reaxys

chromic acid O

Rx-ID: 8261835 View in Reaxys 475/502 Yield

concentrated silver nitrate

benzylethylene oxide

Rx-ID: 8269288 View in Reaxys 476/502 Yield

Conditions & References Porcher; Bulletin de la Societe Chimique de France; vol. <4> 31; (1922); p. 339 View in Reaxys

Mg Br

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H 2N

β-imino-α.γ-diphenyl-butyronitrile

NH 2

Rx-ID: 5698707 View in Reaxys 477/502 Yield

Conditions & References Rondou; Bulletin des Societes Chimiques Belges; vol. 31; (1922); p. 237,238; Chem. Zentralbl.; vol. 94; nb. I; (1923); p. 88 View in Reaxys

O O

OH S OO

O OH

Rx-ID: 6683936 View in Reaxys 478/502 Yield

Conditions & References Soliman; West; Journal of the Chemical Society; (1944); p. 53 View in Reaxys

O O

O HO

S OO

Rx-ID: 7448173 View in Reaxys 479/502 Yield

Conditions & References Beckh; Chemische Berichte; vol. 31; (1898); p. 3163 View in Reaxys

KO H

O HO

Rx-ID: 7449442 View in Reaxys 480/502 Yield

Conditions & References Richard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 200; (1935); p. 1944 View in Reaxys

N N

S Cl

O S

N Cl

O S

N S

Rx-ID: 4996177 View in Reaxys 481/502 Yield

Conditions & References

1 %, 3 %, 4 Time= 80h, Heating, Mechanism %, 6 % Abarca, Belen; Ballesteros, Rafael; Rodrigo, Gemma; Jones, Gurnos; Veciana, Jaume; Vidal-Gancedo, Jose; Tetrahedron; vol. 54; nb. 33; (1998); p. 9785 - 9790 View in Reaxys

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Rx-ID: 6046441 View in Reaxys 482/502 Yield 81%

Conditions & References 9 : Olefination of Methyl Benzyl Ketone with TIPS-propargyl fluorophosphonate Example 9 Olefination of Methyl Benzyl Ketone with TIPS-propargyl fluorophosphonate The reaction was carried out as in Example 2, using methyl benzyl ketone as the carbonyl compound. Obtained in 81percent yield as a circa 1:2 mixture of E:Z isomers: 1 H NMR (CDCl3) δ 1.00 (m, corresponding to 21H of isomer Z), 1.14 (m, corresponding to 21H of isomer E), 2.11 (d, J=4.0 Hz, corresponding to 3H of isomer Z), 2.20 (d, J=3.4 Hz, corresponding to 3H of isomer E), 7.23-7.36 (m, 3H), 7.41-7.50 (m,2H); 19 F NMR δ -108 (s) and -112 (s); IR (film, NaCl) v 3060, 3030, 2950, 2870, 2150, 1645, 1465, 1195, 1065 and 890 cm-1. Analysis calculated for C20 H29 FSi: C: 75.89, H: 9.23. Found: C: 75.88, H: 9.28. Patent; University of Massachusetts; US5917074; (1999); (A1) English View in Reaxys Herstellung von Phenyl-<18-O>aceton Denney; Goldstein; Journal of the American Chemical Society; vol. 79; (1957); p. 4948,4951 View in Reaxys Adcock,W. et al.; Australian Journal of Chemistry; vol. 23; (1970); p. 1921 - 1937 View in Reaxys Fedoronko,M.; Collection of Czechoslovak Chemical Communications; vol. 37; (1972); p. 3897 - 3901 View in Reaxys Reinheckel,H.; Tauber,G.; Monatshefte fuer Chemie; vol. 98; (1967); p. 1944 - 1953 View in Reaxys Oishi,T. et al.; Chemical and Pharmaceutical Bulletin; vol. 17; (1969); p. 2314 - 2318 View in Reaxys Nadon,L. et al.; Canadian Journal of Chemistry; vol. 51; (1973); p. 2366 - 2374 View in Reaxys Huettel,R. et al.; Chemische Berichte; vol. 94; (1961); p. 766 - 780 View in Reaxys Heck,R.F.; Journal of the American Chemical Society; vol. 90; (1968); p. 5538 - 5542 View in Reaxys Zweifel,G. et al.; Journal of the American Chemical Society; vol. 93; (1971); p. 3395 - 3399 View in Reaxys McKillop,A. et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 3635 - 3640 View in Reaxys Trost,B.M. et al.; Journal of the American Chemical Society; vol. 97; nb. 2; (1975); p. 438 - 440 View in Reaxys Mueller,E.; Bauer,M.; Justus Liebigs Annalen der Chemie; vol. 654; (1962); p. 92 - 111 View in Reaxys Lamm,B.; Samuelsson,B.; Acta Chemica Scandinavica (1947-1973); vol. 24; (1970); p. 561 - 568 View in Reaxys Weygand,F.; Bestmann,H.J.; Angewandte Chemie; vol. 72; (1960); p. 535 - 554 View in Reaxys Castelli,F.; Cannone,P.; Bulletin de la Societe Chimique de France; (1974); p. 317 - 330 View in Reaxys Colau,R.; Viel,C.; Bulletin de la Societe Chimique de France; vol. <II>; (1979); p. 362 - 365 View in Reaxys Tamao,K. et al.; Chemistry Letters; (1976); p. 1239 - 1242 View in Reaxys Shono,T. et al.; Chemistry Letters; (1976); p. 1319 - 1322 View in Reaxys Shono,T. et al.; Chemistry Letters; (1977); p. 1021 - 1024 View in Reaxys Granger,R.; Techer,H.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 250; (1960); p. 2581 - 2583

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View in Reaxys Huet,J.; Dreux,J.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 258; (1964); p. 4570 - 4572 View in Reaxys Blatcher,P.; Warren,S.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1979); p. 1074 - 1088 View in Reaxys Padwa,A. et al.; Journal of Organic Chemistry; vol. 33; nb. 4; (1968); p. 1317 - 1322 View in Reaxys Corey,E.J.; Shulman,J.I.; Journal of Organic Chemistry; vol. 35; nb. 3; (1970); p. 777 - 780 View in Reaxys Maycock,A.L.; Berchtold,G.A.; Journal of Organic Chemistry; vol. 35; (1970); p. 2532 - 2538 View in Reaxys DePuy,C.H. et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 2746 - 2750 View in Reaxys Uijttewaal,A.P. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 3157 - 3168 View in Reaxys Goszczynski,S. et al.; Polish Journal of Chemistry; vol. 53; (1979); p. 849 - 853 View in Reaxys Mukaiyama,T. et al.; Tetrahedron Letters; (1968); p. 3787 - 3790 View in Reaxys Sekine,M. et al.; Tetrahedron Letters; (1979); p. 4475 - 4478 View in Reaxys Petragnani,N. et al.; Journal of Organometallic Chemistry; vol. 114; (1976); p. 281 - 292 View in Reaxys Baum; Norman; Journal of the Chemical Society [Section] B: Physical Organic; (1968); p. 227 View in Reaxys Chatterjea; Prasad; Chemische Berichte; vol. 93; (1960); p. 1740,1743 View in Reaxys Juchomenko et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 33; (1963); p. 2528,2464 View in Reaxys Rossi et al.; Helvetica Chimica Acta; vol. 43; (1960); p. 1046,1052 View in Reaxys Sund; Henze; Journal of Chemical and Engineering Data; vol. 15; (1970); p. 200,201 View in Reaxys Eberson; Persson; Journal of Medicinal and Pharmaceutical Chemistry; vol. 5; (1962); p. 738,746 View in Reaxys Patent; Hercules Inc.; GB1170825; (1967) View in Reaxys Birch et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1973); p. 1882,1891 View in Reaxys Fedoronko; Jezo; Collection of Czechoslovak Chemical Communications; vol. 37; (1972); p. 1781,1782-1793 View in Reaxys Truce; Norell; Journal of the American Chemical Society; vol. 85; (1963); p. 3236 View in Reaxys Colonge et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 259; (1964); p. 3566 View in Reaxys Crow; Gosney; Tetrahedron; vol. 26; (1970); p. 1463,1473 View in Reaxys Brown et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 6852 View in Reaxys Pratt; van de Castle; Journal of Organic Chemistry; vol. 26; (1961); p. 2973 View in Reaxys Lee; Tetrahedron Letters; (1966); p. 5669,5672 View in Reaxys Angeloni; Pappalardo; Annali di Chimica (Rome, Italy); vol. 53; (1963); p. 641,645,647 View in Reaxys Dorofeenko et al.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 2424,2476,2478 View in Reaxys Pollini et al.; Farmaco, Edizione Scientifica; vol. 23; (1968); p. 405,406

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View in Reaxys Mueller; Heischkeil; Tetrahedron Letters; (1964); p. 2809,2810 View in Reaxys Hegedus; Stiverson; Journal of the American Chemical Society; vol. 96; (1974); p. 3250,3253 View in Reaxys Cella et al.; Journal of Organic Chemistry; vol. 40; (1975); p. 1860 View in Reaxys Goszczynski; Zielinski; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 24; (1964); p. 239 View in Reaxys Normant; Angelo; Bulletin de la Societe Chimique de France; (1960); p. 357 View in Reaxys Pasto; Snyder; Journal of Organic Chemistry; vol. 30; (1965); p. 1634,1635 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 Olah et al.; Synthesis; (1976); p. 808 View in Reaxys Olah; Ho; Synthesis; (1976); p. 610 View in Reaxys Bellassoued; Gaudemar; Journal of Organometallic Chemistry; vol. 81; (1974); p. 139,141 View in Reaxys Barabas; Balaban; Tetrahedron; vol. 27; (1971); p. 5495,5502 View in Reaxys Buehler et al.; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 48; (1960); p. 48,53 View in Reaxys Biniecki; Herold; Acta poloniae pharmaceutica; vol. 27; nb. 6; (1970); p. 529 - 532 View in Reaxys Rhee et al.; Chemistry Letters; (1978); p. 909 View in Reaxys Possel; Leusen; Tetrahedron Letters; (1977); p. 4229,4230-4231 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 Bunnett; Creary; Journal of Organic Chemistry; vol. 40; (1975); p. 3740,3742-3743 View in Reaxys Singh; Kagan; Journal of Organic Chemistry; vol. 35; (1970); p. 3839,3842 View in Reaxys Cella et al.; Tetrahedron Letters; (1975); p. 4115 View in Reaxys Coulson; Tetrahedron Letters; (1964); p. 3323,3325 View in Reaxys Jones et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 3369 View in Reaxys Stephenson; Falk; Journal of Organic Chemistry; vol. 41; (1976); p. 2928 View in Reaxys Blatcher et al.; Journal of the Chemical Society, Chemical Communications; (1976); p. 547 View in Reaxys Quellette; Levin; Journal of the American Chemical Society; vol. 93; (1971); p. 471,472-476 View in Reaxys Partchamazad et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 282; (1976); p. 69 View in Reaxys Dran et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 272; (1971); p. 1664 View in Reaxys Kakis et al.; Journal of Organic Chemistry; vol. 36; (1971); p. 4117,4122 View in Reaxys Mukaiyama et al.; Chemistry Letters; (1972); p. 237

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View in Reaxys Chavdarian; Heathcock; Journal of the American Chemical Society; vol. 97; (1975); p. 3822 View in Reaxys McKillop et al.; Tetrahedron Letters; (1970); p. 5275 View in Reaxys Puroello; Vullo; Tetrahedron Letters; (1970); p. 5035 View in Reaxys Lethbridge et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1973); p. 35,37 View in Reaxys Nishikawa; Otsu; Kogyo Kagaku Zasshi; vol. 72; (1969); p. 1836; ; vol. 72; nb. 32341; (1970) View in Reaxys Patent; Chisso Corp.; JP6909982; (1966); ; vol. 71; nb. 61016x; (1969) View in Reaxys Botteghi et al.; Chimica e l'Industria (Milan, Italy); vol. 59; (1977); p. 839 View in Reaxys Zielinski; Goszczynski; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 39; (1967); p. 59,60,64 View in Reaxys Ho et al.; Journal of the Chemical Society, Chemical Communications; (1972); p. 791 View in Reaxys Blair; Tate; Journal of the Chemical Society [Section] C: Organic; (1971); p. 1592 View in Reaxys Patent; Hercules Inc.; US3413352; (1968); ; vol. 70; nb. 57430q; (1969) View in Reaxys Tanaka; Tetrahedron Letters; (1979); p. 2601 View in Reaxys Patent; Tisso; JP9892; (1969); Ref. Zh., Khim.; vol. 12; nb. N267P; (1970) View in Reaxys Tantsyura et al.; Metody Polucheniya Khimicheskikh Reaktivov i Preparatov; vol. 26; (1974); p. 155,156; ; vol. 83; nb. 113854p; Chem. Zentralbl.; Ref.Zh.,Khim.1975,Abstr.No.4 N 132 View in Reaxys Patent; ANVAR; FR2354310; (1978); ; vol. 89; nb. 146428 View in Reaxys Patent; Toryanik et al.; SU450792; (1975); Ref. Zh., Khim.; vol. 6; nb. O46P; (1976) View in Reaxys Tagucki; Takigucki; Yuki Gosei Kagaku Kyokaishi; vol. 31; (1973); p. 429 View in Reaxys Rossi; Bunnett; Journal of the American Chemical Society; vol. 94; (1972); p. 683 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 Guyon; Villa; Bulletin de la Societe Chimique de France; (1975); p. 2593,2594, 2598 View in Reaxys Uemura; Nippon Kagaku Zasshi; vol. 89; (1968); p. 692,694; ; vol. 70; nb. 19678u View in Reaxys Bubb; Sternhell; Australian Journal of Chemistry; vol. 29; (1976); p. 1685,1688,1694 View in Reaxys Mukaiyama et al.; Chemistry Letters; (1974); p. 37 View in Reaxys Mondeshka; Angelova; Revue Roumaine de Chimie; vol. 19; (1974); p. 1759,1765 View in Reaxys Rao et al.; Journal of Organometallic Chemistry; vol. 166; (1979); p. 9,10, 12, 15 View in Reaxys Zielinski; Polish Journal of Chemistry; vol. 52; (1978); p. 2233 View in Reaxys Goszczynski; Zielinski; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 39; (1967); p. 53,54,55,57 View in Reaxys Stille; Lau; Journal of the American Chemical Society; vol. 98; (1976); p. 5841,5847 View in Reaxys Selikson; Watt; Journal of Organic Chemistry; vol. 40; (1975); p. 267

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View in Reaxys Corey; Richman; Journal of the American Chemical Society; vol. 92; (1970); p. 5276 View in Reaxys Lichtenberg; Wojcicki; Journal of Organometallic Chemistry; vol. 94; (1975); p. 311,322 View in Reaxys Vinogradov et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 21; (1972); p. 1626; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 21; (1972); p. 1674 View in Reaxys Bagnell et al.; Australian Journal of Chemistry; vol. 27; (1974); p. 2577,2580 View in Reaxys Bunnett; Sundberg; Chemical and Pharmaceutical Bulletin; vol. 23; (1975); p. 2620,2621, 2623-2626 View in Reaxys Alper et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 3611 View in Reaxys Traynelis; Hergenrother; Journal of the American Chemical Society; vol. 86; (1964); p. 298 View in Reaxys Jaeckel; Hanack; Chemische Berichte; vol. 110; (1977); p. 199,207 View in Reaxys Accary et al.; Bulletin de la Societe Chimique de France; (1973); p. 2424,2425,2426 View in Reaxys Corey et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 2645 View in Reaxys Fine; Stern; Journal of Organic Chemistry; vol. 35; (1970); p. 1857 View in Reaxys Bunnett et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 3677,3681 View in Reaxys Goszczynski; Zielinski; Zhurnal Organicheskoi Khimii; vol. 9; (1973); p. 2103,2119,2120 View in Reaxys Unterhalt; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 299; (1966); p. 608,611 View in Reaxys Uemura et al.; Journal of the Chemical Society, Chemical Communications; (1972); p. 234 View in Reaxys Goszczynski; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 25; (1964); p. 1,21,93; ; vol. 63; nb. 4253 View in Reaxys Ridley et al.; Australian Journal of Chemistry; vol. 23; (1970); p. 147,164,179 View in Reaxys Norman; Thomas; Journal of the Chemical Society [Section] B: Physical Organic; (1968); p. 994 View in Reaxys Hanus et al.; Organic Mass Spectrometry; vol. 10; (1975); p. 448,450,451,454 View in Reaxys Campaigne; Johnson; Journal of Heterocyclic Chemistry; vol. 5; (1968); p. 235 View in Reaxys Ogata et al.; Tetrahedron; vol. 24; (1968); p. 1617,1620 View in Reaxys Milstein; Journal of Heterocyclic Chemistry; vol. 5; (1968); p. 339 View in Reaxys Partchamazad et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 266; (1968); p. 717 View in Reaxys Simon et al.; Justus Liebigs Annalen der Chemie; vol. 721; (1969); p. 19 View in Reaxys Zalesskaja; Lavrova; Zhurnal Organicheskoi Khimii; vol. 5; (1969); p. 454,441 View in Reaxys Smith; Waters; Journal of the Chemical Society [Section] B: Physical Organic; (1969); p. 462 View in Reaxys Sethi et al.; Canadian Journal of Chemistry; vol. 47; (1969); p. 1083 View in Reaxys Asinger et al.; Tetrahedron Letters; (1967); p. 631 View in Reaxys Yamamoto et al.; Chemical and Pharmaceutical Bulletin; vol. 16; (1968); p. 2313

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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 Quellette; Levin; Journal of the American Chemical Society; vol. 90; (1968); p. 6889 View in Reaxys Kupin; Petrov; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 975,937 View in Reaxys Combaut; Giral; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 266; (1968); p. 1396 View in Reaxys Accordingly, the following are obtained as preferred products I of the novel process: 1-phenylpropan-2-one, 1-(4-fluorophenyl)-propan-2-one, 1-(2-chlorophenyl)-propan-2-one, 1-(4-methylphenyl)-propan-2-one, 1-(4-methoxyphenyl)-propan-2-one, 1-(3,4-methylenedioxyphenyl)-propan-2-one, 1-(3-methoxy-4-hydroxy)-propan-2-one. Patent; BASF Aktiengesellschaft; US5008461; (1991); (A1) English View in Reaxys Especially useful activated methylene compounds due to their ready availability and the fact that highly useful vinylcyclopropane derivatives are obtained therefrom are: lower alkyl malonates, such as dimethyl malonate, diethyl malonate, dibutyl malonate and diisopropyl malonate; ... methylacetoacetate; ethylacetoacetate; ethyl cyanoacetate; 2,4-pentanedione; phenylacetone; malonamide; malonitrile; and phenylacetonitrile. Patent; Emery Industries, Inc.; US4252739; (1981); (A1) English View in Reaxys Patent; Emery Industries, Inc.; US4328168; (1982); (A1) English View in Reaxys These aldehydes and ketones are set forth for exemplification and are not to be construed as limiting the scope of this invention. benzaldehyde, ... 4-methylsulfinylbenzaldehyde, diphenylacetaldehyde acetophenone, 4-fluoroacetophenone, 1-phenyl-2-propanone, 1-(4-imidazo-1-yl)phenylethanone, 1-phenyl-1-pentanone, diphenyl methanone ... Patent; Schering Corporation; US4376769; (1983); (A1) English View in Reaxys Especially useful activated methylene compounds due to their ready availability and the fact that highly useful vinylcyclopropane derivatives are obtained therefrom are: lower alkyl malonates, such as dimethyl malonate, diethyl malonate, dibutyl malonate and diisopropyl malonate; ...

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methyl acetoacetate; ethyl acetoacetate; ethyl cyanoacetate; 2,4-pentanedione; phenylacetone; malonamide; malonitrile; and phenylacetonitrile. Patent; Emery Industries, Inc.; US4328169; (1982); (A1) English View in Reaxys 6.a : Production of 9-O-propionyl-3"-O-acetoxymethyl-SF-837 substance a. The product of Example 5(b), that is, the 9-O-propionyl-2'-O-acetyl-3"-O-thiomethoxymethyl-SF-837 substance (10 g) was taken up into 320 ml of carbon tetrachloride, and the solution so obtained was then admixed with 80 ml of acetic anhydride and 2 ml of dimethylsulfoxide. The resulting admixture was allowed to stand at 50°C for 10 hours. The reaction mixture was concentrated under a reduced pressure at a temperature of 45°C or less, then admixed with 20 ml of toluene and again concentrated under a reduced pressure. The resulting syrup was dissolved in a small volume of mixture of benzene-acetone (13:1 by volume) and passed downward through a column of silica gel (6 cm in diameter by 27 cm in height). The silica gel column was then eluted with the benzene-acetone (13:1) mixture, and the elude was collected in 10 g fractions. Patent; Meiji Seika Kaisha, Ltd.; US3959256; (1976); (A1) English View in Reaxys Hereinafter there are listed examples of ketones obtainalbe or obtained by the process of the invention: hexanone-3 decanone-4 ... p-tert.butyl-butyrophenone p-nitroacetophenone p-carbomethoxyacetophenone m-carbobutoxy-butyrophenone phenylacetone 4-chlorophenylacetophenone 4-chlorobenzalacetone 2-acetylthiophene Patent; Hoechst Aktiengesellschaft; US4266066; (1981); (A1) English View in Reaxys Compounds of formula I may generate the following organoleptic aryl ketones: ... 1-(2,3-dihydro-1,1,2,3,3,6-hexamethyl-1H-inden-5-yl)-ethanone 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-inden-5-yl]-ethanone 3-methyl-1-(4-methylphenyl)-4-hexen-1-one 5-acetyl-1,1,2,3,3-pentamethylindane 1-phenylpropanone acetophenone* 2,4-dimethylphenyl-ethanone* 1-[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]-ethanone ... Patent; Givaudan Roure ( International ) SA; US6258854; (2001); (B1) English View in Reaxys

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Rx-ID: 24985537 View in Reaxys 483/502 Yield

Conditions & References

88%

89 : Example 89 Example 89 The reaction of Example 86 was repeated, except that 3-phenylpropylene was used in lieu of 3-(4-hydroxyphenyl)propylene. As a result, the conversion of the starting material was 100percent, the yield of the intermediate 1-phenyl-2,2-dimethoxypropane was 88percent, and the yield of the desired phenylacetone was 87percent. Patent; Ube Industries, Ltd.; US4638094; (1987); (A1) English View in Reaxys

Rx-ID: 24985550 View in Reaxys 484/502 Yield

Conditions & References

85%

108 : Example 108 Example 108 The reaction of Example 90 was repeated, except that 3-phenylpropylene was used in lieu of 3-(4-hydroxyphenyl) propylene and that the hydrolysis was carried out at 50° C. for 60 minutes. As a result, the conversion of the starting material was 100percent, the yield of the intermediate 1-phenyl-2,2-di(nbutoxy) propane was 85percent, and the yield of the desired phenylacetone was 83percent. Patent; Ube Industries, Ltd.; US4638094; (1987); (A1) English View in Reaxys

2H 2H

Rx-ID: 7162740 View in Reaxys 485/502 Yield

Conditions & References Phenylaceton, wfr. K2CO3 in D2O Newman,B.C.; Eliel,E.L.; Journal of Organic Chemistry; vol. 35; nb. 11; (1970); p. 3641 - 3646 View in Reaxys 1-Phenyl-2-propanon, D2O, Na-Deuteroxid Coutts et al.; Canadian Journal of Pharmaceutical Sciences; vol. 13; (1978); p. 61,62; ; vol. 90; nb. 71846z View in Reaxys Phenyl-2-propanon, Py., D2O, Natriummethanolat Winnik; Synthetic Communications; vol. 3; (1973); p. 299 View in Reaxys Entspr. nichtdeuterierte Verb., Al2O3, D2O Senn et al.; Journal of the American Chemical Society; vol. 87; (1965); p. 680 View in Reaxys

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O PH (v5)

Rx-ID: 25317413 View in Reaxys 486/502 Yield

Conditions & References 15.b : Compound IV: Q= --CH=CH--; R=benzyl; P,Z,R"=H; R'= --CH2 CH=CH(CH7)3 COOR ''' (b) Trimethylphosphite (124.1 g) was dropwise added to 7.1 g methyliodide at 95°-98° over 15 min. and the mixture was stirred 1 hr. at 98°. Distillation under reduced pressure produced 99percent yield of dimethyl methane phosphate. A solution of 22.4 g of this compound in 15 ml THF was dropwise added to a stirred solution of 122 ml of a 10percent n-BuLi/hexane in 75 ml. THF at -68° to -60° for 40 min. After stirring this mixture under N2 for 1/2 hr. at this temperature, 16.4 g of ethyl phenylacetate in 10 ml THF was added; stirring was continued for 3 hrs. at -68°. By adding water and 6N HCl, the phases separated. The aqueous phase was extracted with CH2 Cl2 which solution was worked up in the usual fashion to produce dimethyl phenylacetylmethane phosphonate (35percent yield). Patent; Abbott Laboratories; US4117014; (1978); (A1) English View in Reaxys

S S O

NH NH

O O

Rx-ID: 25217570 View in Reaxys 487/502 Yield 110 mg (24%)

Conditions & References 8 : 1-(2,3,4,-tri-O-acetyl-α-D-arabinopyranosyl)-3-(benzothiazol-2-yl)-2-thiourea EXAMPLE 8 1-(2,3,4,-tri-O-acetyl-α-D-arabinopyranosyl)-3-(benzothiazol-2-yl)-2-thiourea To 15 ml of anhydrous xylene were added 320 mg (1 mmol) of 2,3,4-tri-O-acetyl-D-arabinopyranosyl isothiocyanate and 150 mg (1 mmol) of 2-aminobenzothiazole (MW 150) and the mixture was treated in the same manner as that used in Example 4, yielding a syrup. The syrup was purified by column chromatography on silica-gel using benzene-acetone as eluent to give the tilted compound from the fraction of benzene-acetone (9:1). Yield: 110 mg (24percent). IR νmax film cm- 1: 3300 (--NH), 1740 (COOCH3), 1600, Patent; Ogura; Haruo; US4025622; (1977); (A1) English View in Reaxys

O O H N

H N

O O

S O

O O O O

Rx-ID: 25217571 View in Reaxys 488/502 Yield 450 mg (75%)

Conditions & References 14 : 1-(2,3,4,5,6-Penta-O-acetyl-D-gluconyl)-3-(benzothiazol-2-yl)-2-thiourea EXAMPLE 14 1-(2,3,4,5,6-Penta-O-acetyl-D-gluconyl)-3-(benzothiazol-2-yl)-2-thiourea

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To 10 ml of anhydrous benzene were added 450 mg (1 mmol) of 2,3,4,5,6-penta-O-acetyl-D-gluconyl isothiocyanate and 150 mg (1 mmol) of 2-aminobenzothiazole and the mixture was heated on a water bath under reflux for 1 hour. After the solvent was distilled off under a reduced pressure, the residue was purified by column chromatography on silica gel using benzene-acetone as eluent to yield the titled compound from the fraction of benzene-acetone (3:1). Yield: 450 mg (75percent). IRνmax film cm- 1: 3350, 3200 (--NH), 1740 (COOCH3), 1605, 1590, 750 (phenyl). Elementary analysis: C24 H27 O11 N3 S2 requires: C, 48.24; H, 4.55; N, 7.03percent. Found: C, 48.42; H, 4.62; N, 7.21percent. Patent; Ogura; Haruo; US4025622; (1977); (A1) English View in Reaxys

O O

H 2N

O S

N O

N H 2N

Rx-ID: 25217572 View in Reaxys 489/502 Yield

Conditions & References

5.06 mg (78%)

21 : 1-phenyl-4-carbamoyl-5-(2,3,4,5,6-penta-O-acetyl-D-gluconylthioureido) pyrazole EXAMPLE 21 1-phenyl-4-carbamoyl-5-(2,3,4,5,6-penta-O-acetyl-D-gluconylthioureido) pyrazole To 15 ml of anhydrous benzene were added 450 mg (1 mmol) of 2,3,4,5,6-penta-O-acetyl-D-gluconyl isothiocyanate and 200 mg (1 mmol) of 1-phenyl-5-aminopyrazol-4-carboxylic acid amide and the mixture was treated in the same manner as that used in Example 19. Purification by column chromatography gave the titled compound from the fraction of benzene-acetone (9:1). Yield: 5.06 mg (78percent). IRνmax KBr cm- 1: 3500 (--NH), 1740 (COOCH3), 1640, 1590, 750 (phenyl). Elementary analysis: C27 H31 O12 N5 S requires: C, 49.92; H, 4.81; N, 10.78percent. Found: C, 50.03; H, 4.78; N, 10.56percent. Patent; Ogura; Haruo; US4025622; (1977); (A1) English View in Reaxys

O O

O HN

O S

N O

Rx-ID: 25217573 View in Reaxys 490/502 Yield 470 mg (80%)

Conditions & References 22 : 1-(4-Pyridylcarbonyl)-4-(2,3,4,5,6-penta-O-acetyl-D-gluconyl)-thiosemicarbazide EXAMPLE 22 1-(4-Pyridylcarbonyl)-4-(2,3,4,5,6-penta-O-acetyl-D-gluconyl)-thiosemicarbazide To 10 ml of anhydrous benzene were added 450 mg (1 mmol) of 2,3,4,5,6-penta-O-acetyl-D-gluconyl isothiocyanate and 137 mg (1 mmol) of isonicotinic acid hydrazide and the mixture was treated in the same manner as that used in Example 19. Purification by column chromatography gave the titled compound from the fraction of benzeneacetone (9:1). Yield: 470 mg (80percent). IRνmax KBr cm- 1: 3350, 3200 (--NH), 1740 (COOCH3), 1700 (ketone). Elementary analysis: C23 H28 O12 N4 S requires: C, 47.26; H, 4.83; N, 9.58percent. Found: C, 47.52; H, 4.78; N, 9.56percent.

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Patent; Ogura; Haruo; US4025622; (1977); (A1) English View in Reaxys 2

Rx-ID: 7178086 View in Reaxys 491/502 Yield

Conditions & References Phenylessigsaeurechlorid, Zn/CH3I Su,D.T.T.; Thornton,E.R.; Journal of the American Chemical Society; vol. 100; nb. 6; (1978); p. 1872 - 1875 View in Reaxys Entspr. Keton, DBr, CD3OD Gaudry; Marquet; Tetrahedron; vol. 26; (1970); p. 5617,5624 View in Reaxys

14C

Rx-ID: 7594264 View in Reaxys 492/502 Yield

Conditions & References (Na-ethylat), Benzylcyanid, Ethylacetat (14C=O) Mezoe et al.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 70; (1971); p. 83,86, 88 View in Reaxys Phenylacetyl-1-C14-chlorid, Dimethylcadmium Roberts; Douglass; Journal of Organic Chemistry; vol. 28; (1963); p. 1225,1228 View in Reaxys (yield)87percent Roberts; Douglass; Journal of Organic Chemistry; vol. 28; (1963); p. 1225,1228 View in Reaxys Phenylessigsaeure-1-14C, CH3Li, sd. Ae. Eberson; Acta Chemica Scandinavica (1947-1973); vol. 17; (1963); p. 2349 View in Reaxys 2H 2H

Rx-ID: 7161163 View in Reaxys 493/502 Yield

Conditions & References Phenylaceton, D2O, HCl, Δ Singh; Kagan; Journal of Organic Chemistry; vol. 35; (1970); p. 3839,3842 View in Reaxys Phenyl-2-propanon, Py., D2O Winnik; Synthetic Communications; vol. 3; (1973); p. 299 View in Reaxys

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Rx-ID: 7658484 View in Reaxys 494/502 Yield

Conditions & References Phenylessigsaeure-d7, MeLi Najjar; Blake; Benoit; Lu; Journal of Medicinal Chemistry; vol. 21; nb. 6; (1978); p. 555 - 558 View in Reaxys 2

O2H

2 H 2H

2H 2H

Rx-ID: 7676074 View in Reaxys 495/502 Yield

Conditions & References Phenylessigsaeure-d7, CD3Li Najjar; Blake; Benoit; Lu; Journal of Medicinal Chemistry; vol. 21; nb. 6; (1978); p. 555 - 558 View in Reaxys

2H 2H 2H

Rx-ID: 7161713 View in Reaxys 496/502 Yield

Conditions & References d(6)-Acetanhydrid, Phenylessigsaeure Hanus et al.; Organic Mass Spectrometry; vol. 10; (1975); p. 448,450,451,454 View in Reaxys Phenyl-2-propanon-1,1,3,3,3-d(5), Pyridin, Wasser Winnik; Synthetic Communications; vol. 3; (1973); p. 299 View in Reaxys

H O

Rx-ID: 7654716 View in Reaxys 497/502 Yield

Conditions & References Entspr. Keton, DBr, CD3OD Gaudry; Marquet; Tetrahedron; vol. 26; (1970); p. 5617,5624 View in Reaxys H

13C 2

13CH

Rx-ID: 7189245 View in Reaxys 498/502 Yield

Conditions & References Phenyl-(1,2-13C(2))-essigsaeure, 13C-Methyllithium Pomerantz; Fink; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 16; nb. 2; (1979); p. 275 - 286 View in Reaxys

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14C 2

Rx-ID: 7278538 View in Reaxys 499/502 Yield

Conditions & References Verb.6, CuCl2/CuO, Acn. Pichat; Beaucourt; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 12; (1976); p. 31,32,35 View in Reaxys H C–

Rx-ID: 7022432 View in Reaxys 500/502 Yield

Conditions & References Phenylaceton, Dimsyl-Na Bradamaule et al.; Journal of the Chemical Society, Chemical Communications; (1976); p. 478 View in Reaxys

13C

Rx-ID: 7189055 View in Reaxys 501/502 Yield

Conditions & References <2-13C>-1-Diazo-1-phenyl-2-propanon 3e Zeller; Chemische Berichte; vol. 112; (1979); p. 678,679-688 View in Reaxys

O O

rel-configuration

Rx-ID: 22987397 View in Reaxys 502/502 Yield 95 %, 4 %

Conditions & References 15 Product distribution / selectivity Patent; Samsung Fine Chemicals Co., Ltd.; Pohang University of Science and Technology; US6753443; (2004); (B1) English View in Reaxys

91 %, 7 %

12 Product distribution / selectivity Patent; Samsung Fine Chemicals Co., Ltd.; Pohang University of Science and Technology; US6753443; (2004); (B1) English View in Reaxys

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