Cyclopentanone by Asch

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449 reactions in Reaxys

2017-10-23 09h:39m:21s (EST)

449 reactions in Reaxys

2017-10-23 09h:40m:00s (EST)

1. Query

Search as: As drawn, No salts, No mixtures, No isotopes, No charges, No radicals 2. Query

(1. Query) AND itemno in (1)

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Rx-ID: 276443 View in Reaxys 1/449 Yield 10.2 %, 6.5 %

Conditions & References With C11H14FeN3O11S*3H2O, dihydrogen peroxide, nitric acid in water, acetonitrile, Time= 6h, T= 25 °C , p= 760.051Torr , Reagent/catalyst, Overall yield = 16.7 percent Kopylovich, Maximilian N.; Mac Leod, Tatiana C. O.; Mahmudov, Kamran T.; Pombeiro, Armando J. L.; Haukka, Matti; Amanullayeva, Gunel I.; Journal of Inorganic Biochemistry; vol. 115; (2012); p. 72 - 77,6 View in Reaxys With air, T= 140 °C , p= 20594.2Torr Patent; Phillips Petr. Co.; US2452741; (1947) View in Reaxys

1 % Chromat., 91 % Chromat.

With sodium periodate, lt;RuO2(bipy)lt;IO3(OH)3gt;gt;*1.5H2O in dichloromethane, water, Time= 15h, T= 80 °C , Title compound not separated from byproducts Bailey, Alan J.; Griffith, William P.; Savage, Paul D.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 21; (1995); p. 3537 - 3542 View in Reaxys

13 % Chromat., 14 % Chromat.

With 1-diazo-2,3,4,5-tetrachlorocyclopenta-2,4-diene, oxygen, Photolysis, Oxidation

2 % Chromat., 5 % Chromat.

With lt;Fe(μ-O2)(μ-PXDK)(O2CPhCy)2(Bu-Im)2gt;, Time= 0.0833333h, T= -80 - 20 °C , other temperatures, reaction

Dunkin, Ian R.; McCluskey, Adam; Bulletin of the Chemical Society of Japan; vol. 71; nb. 6; (1998); p. 1397 - 1400 View in Reaxys

times, effects of O2 and additives, Product distribution LeCloux, Daniel D.; Barrios, Amy M.; Lippard, Stephen J.; Bioorganic and Medicinal Chemistry; vol. 7; nb. 5; (1999); p. 763 - 772 View in Reaxys

66 % Chromat., 4 % Chromat.

With tetra-n-butylammonium nitridoosmate(VIII), iron(III) chloride in dichloromethane, acetic acid, Time= 0.00833333h, T= 23 °C , Product distribution Yiu, Shek-Man; Wu, Zhi-Biao; Mak, Chi-Keung; Lau, Tai-Chu; Journal of the American Chemical Society; vol. 126; nb. 45; (2004); p. 14921 - 14929 View in Reaxys

11 % Chro- With potassium permanganate, boron trifluoride acetonitrile complex in acetonitrile, T= 24.85 °C , Kinetics mat., 39 % Lam, William W. Y.; Yiu, Shek-Man; Lee, Joyce M. N.; Yau, Sammi K. Y.; Kwong, Hoi-Ki; Lau, Tai-Chu; Liu, Chromat. Dan; Lin, Zhenyang; Journal of the American Chemical Society; vol. 128; nb. 9; (2006); p. 2851 - 2858 View in Reaxys With [Cu3(.mu.3-OH)(pyrazolate)3(acetate)2(pyrazole)], dihydrogen peroxide, nitric acid in water, acetonitrile, Time= 6h, T= 25 °C , p= 760.051Torr Di Nicola, Corrado; Garau, Federica; Karabach, Yauhen Y.; Martins, Luisa M. D. R. S.; Monari, Magda; Pandolfo, Luciano; Pettinari, Claudio; Pombeiro, Armando J. L.; European Journal of Inorganic Chemistry; nb. 5; (2009); p. 666 - 676 View in Reaxys 9.1 With dihydrogen peroxide in water, acetonitrile, Time= 5h, T= 50 °C , p= 760.051Torr %ChroKirillova, Marina V.; Kirillov, Alexander M.; Guedes Da Silva, M. Fatima C.; Pombeiro, Armando J. L.; Europemat., 0.8 %Chromat. an Journal of Inorganic Chemistry; nb. 22; (2008); p. 3423 - 3427 View in Reaxys With Cr2O4 (2-)*Cu(2+), dihydrogen peroxide in acetonitrile, Time= 10h, T= 50 °C

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Acharyya, Shankha S.; Ghosh, Shilpi; Adak, Shubhadeep; Tripathi, Deependra; Bal, Rajaram; Catalysis Communications; vol. 59; (2015); p. 145 - 150 View in Reaxys 3.3. Typical Procedures for the Catalytic Oxidation of Cycloalkanes and Product Analysis General procedure: The peroxidative oxidation reactions were typically carried out as follows: 0.1–20 μmol of the catalystwas added to 5.00 mmol of the cycloalkane, whereafter 10.00 mmol of 30percent H2O2 (1.02 mL) or of 70percentTBHP (688 μL) were added and the reaction solution was stirred for 10 h at r.t. and normal pressure.In the experiments with radical traps, CBrCl3 (5.00 mmol) or NHPh2 (5.00 mmol) was added to thereaction mixture. With [Cu3(μ3-5-(4-pyridyl)tetrazolate)4(μ2-N3)2(DMF)2]n·(DMF)2n, dihydrogen peroxide in neat (no solvent), Time= 10h, T= 20 °C , p= 760.051Torr , Green chemistry, Catalytic behavior, Reagent/catalyst Martins, Luísa; Nasani, Rajendar; Saha, Manideepa; Mobin, Shaikh; Mukhopadhyay, Suman; Pombeiro, Armando; Molecules; vol. 20; nb. 10; (2015); p. 19203 - 19220 View in Reaxys With [{Cu2(μ2-Hedea)2}2(μ4-pma)]n·4nH2O, dihydrogen peroxide, trifluoroacetic acid in water, acetonitrile, Time= 5h, T= 50 °C , Catalytic behavior, Reagent/catalyst, Overall yield = 35.5 percent Fernandes, Tiago A.; Santos, Carla I. M.; André, Vânia; Kłak, Julia; Kirillova, Marina V.; Kirillov, Alexander M.; Inorganic Chemistry; vol. 55; nb. 1; (2016); p. 125 - 135 View in Reaxys With tert.-butylhydroperoxide in water, Time= 24h, T= 20 °C , Green chemistry Denicourt-Nowicki, Audrey; Lebedeva, Anastasia; Bellini, Clément; Roucoux, Alain; ChemCatChem; vol. 8; nb. 2; (2016); p. 357 - 362 View in Reaxys 5 : Example 5 The catalyst dissolved in the fresh cyclopentane added to the system is metal phthalocyanine (R1 = H, R2 = CH3CH2, M = Co) having the general formula (IV)And cobalt naphthenate,The total concentration was 45 ppm.When the device is in steady state,The flow rate of fresh cyclopentane fed to the oxidation reactor was 11.1 mL / h,The average residence time of the oxidation reactor in liquid phase was 1.3 h,The pressurized pure oxygen was continuousInto the oxidation reactor,Maintaining the system reaction temperature of 165 ,The reaction pressure was 2.6 MPa.After sampling analysis,The conversion of cyclopentane in the system was 99.4percentThe total selectivity of cyclopentanol and cyclopentanone was 95.1percentThe selectivity of cyclopentanol was 32.1percentThe selectivity to cyclopentanone was 63.0percent. With C40H32CoN8, oxygen, Time= 1.3h, T= 165 °C , p= 19502Torr , Reagent/catalyst, Temperature, Pressure Patent; Quzhou Qunying Chemical Industry Co., Ltd.; Wang, Qinbo; Xiong, Zhenhua; Chen, Chuxiong; (17 pag.); CN105237355; (2016); (A) Chinese View in Reaxys 25 : Example 25 The catalyst dissolved in fresh cyclopentane was added to the systemManganese acetylacetonate withN, N'-dihydroxyphthalimide,The total concentration was 120 ppm.When the device is in steady state,The flow rate of fresh cyclopentane in the oxidation reactor was 3.4 mL / h,In this case, the average residence time of the oxidation reactor in liquid phase was 2.3 h,The pressurized pure oxygen is continuously fed into the oxidation reactor,The reaction temperature was maintained at 152 ,The reaction pressure was 2.8 MPa.After sampling analysis,The conversion of cyclopentane in the system was 99.3percentThe total selectivity of cyclopentanol and cyclopentanone was 98.6percentThe selectivity of cyclopentanol was 64.3percentThe selectivity to cyclopentanone was 34.3percent. With bis(acetylacetonato)manganese(II), oxygen, Time= 1.3h, T= 165 °C , p= 19502Torr , Reagent/catalyst, Temperature, Pressure Patent; Quzhou Qunying Chemical Industry Co., Ltd.; Wang, Qinbo; Xiong, Zhenhua; Chen, Chuxiong; (17 pag.); CN105237355; (2016); (A) Chinese View in Reaxys Alkane oxidation reactions General procedure: The alkane oxidation reactions were performed in air atmosphere in thermostated glass reactors equipped with a condenserunder vigorous stirring at 50°C and using MeCN as solvent (upto 5 mL total volume). In a

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typical experiment, catalyst 1 or 2(10 mol) and gas chromatography (GC) internal standard (MeNO2,50 L) were introduced into the MeCN solution, followed by the addition of an acid promoter (typically 0.1 mmol, optional) used asa stock solution in MeCN. An alkane or alcohol substrate (2 mmol) was then introduced, and the reaction started upon addition of hydrogen peroxide (50percent in H2O, 10 mmol) in one portion. The oxidation reactions were monitored by withdrawing small aliquots after different periods of time, which were treated with PPh3(following the Shul’pin’s method [24]) for the reduction of remaining H2O2 and alkyl hydroperoxides that are typically formed as primary products in alkane oxidations. The samples were analyzedby GC using nitromethane as an internal standard. Attribution ofpeaks was made by comparison with chromatograms of authentic samples. For comparative purposes, the oxidation of cyclohexanol to cyclohexanone was also investigated, following the abovementioned experimental procedure. Blank tests confirmed that alkane oxidations do not proceed in the absence of copper catalyst. With C36H50Cu2N4O4 (2+)*2NO3 (1-), dihydrogen peroxide, trifluoroacetic acid in water, acetonitrile, Time= 3h, T= 50 °C , Reagent/catalyst, Overall yield = 9 percent Fernandes, Tiago A.; André, Vânia; Kirillov, Alexander M.; Kirillova, Marina V.; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 357 - 367 View in Reaxys OH

Rx-ID: 276670 View in Reaxys 2/449 Yield 100 %

Conditions & References With water, nickel dibromide, dibenzoyl peroxide in N,N-dimethyl acetamide, Time= 3h, T= 60 °C Youm, Jennessa Ji Youn; Schlaf, Marcel; Bierenstiel, Matthias; Tetrahedron Letters; vol. 49; nb. 20; (2008); p. 3199 - 3203 View in Reaxys

100 %

12 :General procedure: synthesis of ketones by dehydrogenation oxidation reaction of alcohol>the complex 1 used in the catalyst, the dehydrogenation oxidation of a variety of secondary alcohols with the reaction conditions as shown in Table 3 Reaction was carried out.After completion of the reaction, the reaction solution was analyzed by GC, and it was confirmed that the corresponding ketone was formed with high conversion and high yield in all cases With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in hexane, Time= 20h, Reflux, Solvent Patent; KANTO CHEM CO INC; YAMAGUCHI, RYOHEI; FUJITA, KENICHI; (38 pag.); JP2015/83544; (2015); (A) Japanese View in Reaxys

99 %

With allyl methyl carbonate, dihydridotetrakis(triphenylphosphine)ruthenium(II) in toluene, Time= 13h, T= 100 °C Minami, Ichiro; Shimizu, Isao; Tsuji, Jiro; Journal of Organometallic Chemistry; vol. 296; (1985); p. 269 - 280 View in Reaxys

99 %

With air, potassium carbonate, Time= 7h, T= 100 °C Lakshmi Kantam; Arundhathi; Likhar, Pravin R.; Damodara; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2633 - 2637 View in Reaxys

99 %

With dihydrogen peroxide in water, Time= 8h, T= 89.84 °C Ding, Yong; Zhao, Wei; Ma, Bao-Chun; Qiu, Wen-Yuan; Canadian Journal of Chemistry; vol. 89; nb. 1; (2011); p. 13 - 18 View in Reaxys

99 %

With dihydrogen peroxide, Time= 3h, T= 80 °C , Autoclave, neat (no solvent) Wang, Xiaoli; Wu, Gongde; Wei, Wei; Sun, Yuhan; Transition Metal Chemistry; vol. 35; nb. 2; (2010); p. 213 - 220 View in Reaxys

98 %

With dihydrogen peroxide in water, Time= 2.5h, T= 20 °C

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Eshtiagh-Hosseini, Hossein; Tabari, Taymaz; Eshghi, Hossein; Asian Journal of Chemistry; vol. 25; nb. 6; (2013); p. 3307 - 3312 View in Reaxys 98 %

A typical procedure for the catalytic oxidation of alcohols General procedure: The catalyst solutionwas prepared by dissolving complex 3(36.1 mg,0.05mmol) in methanol (5.0 mL).Under a nitrogen atmosphere, the mixture of an alcohol substrate (2.0 mmol) and1.0 mL of the catalyst solution (0.01mmol) in 20mL acetone was stirred at 56 Cfor 10 minutes. tBuOK(22.4mg, 0.2 mmol)was then added to initiate the reaction.At the stated time, 0.1 mL of the reaction mixture was sampled and immediately diluted with 0.5 mL acetone pre-cooled-to-0 C for GC or NMR analysis. After the reaction was complete, the reaction mixture was condensed under reduced pressure and subject to purification by flash silica gel column chromatography to afford the corresponding ketone product, which was identified by comparison with the authentic sample through NMR and GC analysis. With [(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine)RuCl2(PPh3)], potassium tert-butylate, acetone in methanol, Time= 0.166667h, T= 56 °C , p= 750.075Torr , Inert atmosphere, Oppenauer Oxidation, Catalytic behavior Wang, Qingfu; Du, Wangming; Liu, Tingting; Chai, Huining; Yu, Zhengkun; Tetrahedron Letters; vol. 55; nb. 9; (2014); p. 1585 - 1588 View in Reaxys

97 %

With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 in acetonitrile, Time= 0.666667h, Heating, Oxidation Minghu, Wu; Guichun, Yang; Zuxing, Chen; Synthetic Communications; vol. 30; nb. 17; (2000); p. 3127 - 3131 View in Reaxys

97.1 %

With oxygen in water, Time= 24h, T= 80 °C , p= 760.051Torr Wang, Tao; Shou, Heng; Kou, Yuan; Liu, Haichao; Green Chemistry; vol. 11; nb. 4; (2009); p. 562 - 568 View in Reaxys

97 %

With dihydrogen peroxide in water, tert-butyl alcohol, Time= 24h, T= 80 °C Yamada, Yoichi M.A.; Jin, Chung Keun; Uozumi, Yasuhiro; Organic Letters; vol. 12; nb. 20; (2010); p. 4540 4543 View in Reaxys

96 %

With Oxonereg; in water, Time= 21h, T= 70 °C , chemoselective reaction Wu, Shang; Ma, Hengchang; Lei, Ziqiang; Synlett; nb. 18; (2010); p. 2818 - 2822 View in Reaxys

96.1 %

With tert.-butylhydroperoxide, C48H45Cu4N16O14, potassium carbonate in water, Time= 4h, T= 80 °C , Microwave irradiation, Reagent/catalyst Kopylovich, Maximilian N.; Mizar, Archana; Guedes Da Silva, M. Fatima C.; Mac Leod, Tatiana C. O.; Mahmudov, Kamran T.; Pombeiro, Armando J. L.; Chemistry - A European Journal; vol. 19; nb. 2; (2013); p. 588 - 600 View in Reaxys

96 %

With dihydrogen peroxide in water, Time= 12h, T= 80 °C , 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

96 %

With [Fe(1,1′-methylene-3,3′-di-benzylimidazole-2-ylidene)(bipy)I2] in neat (no solvent), Time= 8h, T= 80 °C , Inert atmosphere, Schlenk technique, Catalytic behavior Pinto, Mara F.; Cardoso, Bernardo De P.; Barroso, Sónia; Martins, Ana M.; Royo, Beatriz; Dalton Transactions; vol. 45; nb. 34; (2016); p. 13541 - 13546 View in Reaxys

95 %

With [Cp*Ru(μ-Cl)3RuCl(PPh3)2], potassium carbonate in dichloromethane, butanone, Heating

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Da Silva, Ana C.; Piotrowski, Holger; Mayer, Peter; Polborn, Kurt; Severin, Kay; European Journal of Inorganic Chemistry; nb. 3; (2001); p. 685 - 691 View in Reaxys 95 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, tert.-butylnitrite, oxygen in 1,2-dichloro-ethane, Time= 12h, p= 1500.15Torr , Autoclave, Heating He, Xijun; Shen, Zhenlu; Mo, Weimin; Sun, Nan; Hu, Baoxiang; Hu, Xinquan; Advanced Synthesis and Catalysis; vol. 351; nb. 1-2; (2009); p. 89 - 92 View in Reaxys

95 %

With tert.-butylhydroperoxide in decane, acetonitrile, Time= 2.5h, T= 65 °C Verma, Sanny; Nandi, Mahasweta; Modak, Arindam; Jain, Suman L.; Bhaumik, Asim; Advanced Synthesis and Catalysis; vol. 353; nb. 11-12; (2011); p. 1897 - 1902 View in Reaxys

94 %

With N-methylpyrrolidine-2-one hydrotribromide, dihydrogen peroxide in acetonitrile, Time= 0.42h, Heating Joseph, Jomy K.; Jain, Suman L.; Sain, Bir; European Journal of Organic Chemistry; nb. 3; (2006); p. 590 - 594 View in Reaxys

94 %

With tert.-butylhydroperoxide in decane, acetonitrile, Time= 0.333333h, T= 65 °C Mungse, Harshal P.; Verma, Sanny; Kumar, Neeraj; Sain, Bir; Khatri, Om P.; Journal of Materials Chemistry; vol. 22; nb. 12; (2012); p. 5427 - 5433 View in Reaxys

93 %

With sodium bromate, hydrogen bromide in acetic acid, Time= 3h, T= 40 °C Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Yamasaki, Hiromochi; Fujisaki, Shizuo; Bulletin of the Chemical Society of Japan; vol. 59; nb. 3; (1986); p. 747 - 750 View in Reaxys

93 %

With tert.-butylhydroperoxide in water, acetonitrile, T= 80 °C Dhanalaxmi, Karnekanti; Singuru, Ramana; Kundu, Sudipta K.; Reddy, Benjaram Mahipal; Bhaumik, Asim; Mondal, John; RSC Advances; vol. 6; nb. 43; (2016); p. 36728 - 36735 View in Reaxys

92 %

With potassium carbonate, Time= 5h, T= 100 °C , Neat (no solvent) Layek, Keya; Maheswaran; Arundhathi; Kantam, M. Lakshmi; Bhargava, Suresh K.; Advanced Synthesis and Catalysis; vol. 353; nb. 4; (2011); p. 606 - 616 View in Reaxys

92 %

2.2. Oxidation of alcohols under ultrasonic condition: a general procedure General procedure: A mixture of alcohol (10 mmol), Ni(NO3)2*6H2O (2.908 g, 10 mmol), I2 (1.3 g, 10 mmol) and water (2 mL) were sonicated in a sonic bath working at 35 kHz (constant frequency) maintained at 25 °C by circulating water. After completion of the reaction (Table 5, monitored on TLC), the product was taken into diethyl ether (10 mL), the organic matter was washed with sat. NaHCO3 (2.5 mL), water (5 mL) and then dried over anhydrous Na2SO4. The organic layer was evaporated in a fume hood to get almost pure aldehyde. The crude was then subjected to silica gel column chromatography to get the pure product. All the products were characterized by IR, GC– mass spectral analysis; and the physical properties were compared with the properties of authentic samples. With nickel(II) nitrate hexahydrate, iodine in water, Time= 0.0333333h, T= 25 °C , Sonication Pasha, Mohamed Afzal; Nagashree, Shrivatsa; Ultrasonics Sonochemistry; vol. 20; nb. 3; (2013); p. 810 - 814 View in Reaxys

92 %

With aluminum oxide in N,N-dimethyl-formamide, Time= 10h, T= 120 °C , Inert atmosphere Damodara, Dandu; Arundhathi, Racha; Likhar, Pravin R.; Advanced Synthesis and Catalysis; vol. 356; nb. 1; (2014); p. 189 - 198 View in Reaxys

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92 %

With [(η5-Cp*)Ir(1-benzyl-3-phenylselenomethyl-1,3-dihydrobenzoimidazole-2-selenone)Cl][PF6], potassium tert-butylate, acetone, Time= 3h, T= 80 °C , Reagent/catalyst Sharma, Alpesh K.; Joshi, Hemant; Bhaskar, Renu; Singh, Ajai K.; Dalton Transactions; vol. 46; nb. 7; (2017); p. 2228 - 2237 View in Reaxys

91 %

With chromium(VI) oxide, aluminum oxide in hexane, Time= 15h, T= 39.9 °C Hirano, Masao; Nagasawa, Sonoko; Morimoto, Takashi; Bulletin of the Chemical Society of Japan; vol. 64; nb. 9; (1991); p. 2857 - 2859 View in Reaxys

91 %

With dihydrogen peroxide, bromine in dichloromethane, water, Time= 2h, T= 20 °C Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 261 - 269 View in Reaxys

90 %

With pyridine, tert-butylhypochlorite in dichloromethane, Time= 1h Milovanovic, Jovan N.; Vasojevic, Miorad; Gojkovic, Svetislav; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1988); p. 533 - 536 View in Reaxys

90 %

With aluminum (III) chloride, Oxonereg; in water, Time= 4h, T= 20 °C Wu, Shang; Ma, Hengchang; Lei, Ziqiang; Tetrahedron; vol. 66; nb. 45; (2010); p. 8641 - 8647 View in Reaxys

90 %

With dihydrogen peroxide in water, acetonitrile, Time= 3.75h, T= 25 °C Eshtiagh-Hosseini, Hossein; Tabari, Taymaz; Takjoo, Reza; Eshghi, Hossein; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 43; nb. 3; (2013); p. 264 - 272 View in Reaxys

90 %

With tert.-butylhydroperoxide, thiourea S,S-dioxide in dodecane, acetonitrile, Time= 4h, T= 65 °C Verma, Sanny; Singh, Raghuvir; Tripathi, Deependra; Gupta, Piyush; Bahuguna, Gajendra Mohan; Jain, Suman L.; RSC Advances; vol. 3; nb. 13; (2013); p. 4184 - 4188 View in Reaxys

90 %

Oxidation of alcohols 10 to carbonyl compounds 11 General procedure: A 25 mL round bottom flask was charged with alcohol (1.0 mmol), catalyst (0.02 equiv.), MeCN (5 mL), TBHP (1.5 M solution in dodecane; 1.5 equiv.) and then stirred at 65 °C for 1 h. According to Table 2, all reactions require 1 h. At the end of the reaction, the catalyst was filtered at room temperature over membrane filter paper and reused for subsequent runs. The filtrate so obtained was concentrated under reduced pressure and the residue was dissolved in dichloromethane (20 mL). The organic layer was washed with brine solution (10 mL 3×). The organic layer was dried over anhydrous MgSO4 and then, concentrated under reduced pressure. Product was purified by column chromatography over silica gel. The isolated yield of the obtained product was found to be 94percent and the conversion was determined by the GC–MS analysis. The purity of the products was determined by comparing the 1H NMR spectra of the products with those of authentic samples. With tert.-butylhydroperoxide in dodecane, acetonitrile, Time= 1h, T= 65 °C Verma, Sanny; Le Bras, Jean; Jain, Suman L.; Muzart, Jacques; Applied Catalysis A: General; vol. 468; (2013); p. 334 - 340 View in Reaxys

90 %

With tert.-butylhydroperoxide in water, Time= 3h, T= 60 °C Patnam, Padma L.; Bhatt, Mukesh; Singh, Raghuvir; Saran, Sandeep; Jain, Suman L.; RSC Advances; vol. 6; nb. 65; (2016); p. 60888 - 60895 View in Reaxys

89.9 %

7B; 14

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With trichloroisocyanuric acid, tetrabutylammomium bromide, water, potassium carbonate, ruthenium trichloride in ethyl acetate, Time= 1 - 3h, T= 20 - 45 °C , Product distribution / selectivity Patent; Nagase & Co., Ltd.; Nagase Chemtex Corporation; JP2005/75784; (2005); (A) Japanese View in Reaxys 89 %

With morpholinium fluorochromate(VI) absorbed on wet silica gel in hexane, Time= 0.35h, T= 20 °C Sayyed-Alangi, S. Zahra; Sajjadi-Ghotbabadi; Baei, Mohammed T.; Naderi, Sahar; E-Journal of Chemistry; vol. 8; nb. 2; (2011); p. 815 - 818 View in Reaxys

88 %

With air, bis(salicylideniminato-3-propyl)methylamino-cobalt(III), 2,6-dimethoxy-p-quinone, [C5Ph4O(Ru(CO)2)]2H2 in toluene, Time= 1h, T= 100 °C Csjernyik, Gabor; Ell, Alida H.; Fadini, Luca; Pugin, Benoit; Baeckvall, Jan-E.; Journal of Organic Chemistry; vol. 67; nb. 5; (2002); p. 1657 - 1662 View in Reaxys

88 %

With dihydrogen peroxide, benzyltrimethylammonium bromide dibromide in water, acetonitrile, Time= 3h, T= 60 °C , Green chemistry Dey, Madhudeepa; Dhar, Siddhartha Sankar; Kalita, Mukul; Synthetic Communications; vol. 43; nb. 12; (2013); p. 1734 - 1742 View in Reaxys

88 %

With DHPDMDO in acetonitrile, Time= 0.583333h, T= 20 °C Azarifar, Davood; Najminejad, Zohreh; Khosravi, Kaveh; Journal of the Iranian Chemical Society; vol. 10; nb. 5; (2013); p. 979 - 983 View in Reaxys

88 %

With oxygen in water, Time= 1h, T= 100 °C , p= 37503.8Torr , Flow reactor, Green chemistry Osako, Takao; Torii, Kaoru; Uozumi, Yasuhiro; RSC Advances; vol. 5; nb. 4; (2015); p. 2647 - 2654 View in Reaxys

87 %

With ruthenium trichloride, potassium hydroxide, potassium peroxomonosulphate, Time= 2h, Ambient temperature Green, Graham; Griffith, William P.; Hollinshead, David M.; Ley, Steven V.; Schroeder, Martin; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1984); p. 681 686 View in Reaxys

87 %

With ferric(III) bromide, dihydrogen peroxide, Time= 24h, T= 20 °C Martin, Sandra E.; Garrone, Analia; Tetrahedron Letters; vol. 44; nb. 3; (2003); p. 549 - 552 View in Reaxys

87 %

With oxygen in toluene, Time= 1h, T= 80 °C Kantam, M. Lakshmi; Pal, Ujjwal; Sreedhar; Bhargava, Suresh; Iwasawa, Yasuhiro; Tada, Mizuki; Choudary; Advanced Synthesis and Catalysis; vol. 350; nb. 9; (2008); p. 1225 - 1229 View in Reaxys

87.2 %

With C31H29ClN4OPRuS(1+)*F6P(1-), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Catalytic behavior, Reagent/catalyst Sarkar, Shyamal Kumar; Jana, Mahendra Sekhar; Mondal, Tapan Kumar; Sinha, Chittaranjan; Applied Organometallic Chemistry; vol. 28; nb. 8; (2014); p. 641 - 651 View in Reaxys

87 %

2.3. General procedure for oxidation of alcohols General procedure: A mixture of S4SiIL or S3PIL (0.05mmol) and alcohol (30mmol) in a 25 mL flask fitted with a reflux condenser was heated to the reactiontemperature, then the required amount of aqueous H2O2 was addeddropwise under stirring. The progress of the reaction was monitored by TLC (GF254 silica gel coloration in phosphomolybdic acid/ethanol for aromatic alcohol, in KMnO4 solution for aliphatic alcohol). After the completion, the reac-

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tion mixture was extracted with diethyl ether(3 × 20 mL), solvent was evaporated in a vacuum. The residual was analyzedby gas chromatography (HP 6890) equippedwith a flame ionizationdetector and an SE-54 column. The aqueous phase was subjected torotary evaporation, and then was dried at 85 °C under a vacuum for 8 hto give regenerated ionic liquids. Pure oxidation products were obtainedby column chromatography (petroleum ether-ethyl acetate 9:1 (V/V))and identified by the comparison of their IR and 1H NMR spectra withthose of authentic samples. With O40SiW12 (4-)*4C17H38NO3S(1+), dihydrogen peroxide, Time= 4h, T= 70 °C , Green chemistry, Reagent/catalyst Li, Xinzhong; Cao, Rong; Lin, Qi; Catalysis Communications; vol. 69; (2015); p. 5 - 10 View in Reaxys 86 %

With aluminum oxide, ammonium chlorochromate in cyclohexane, Time= 3h, T= 60 °C Zhang, Gui-Sheng; Shi, Qi-Zeng; Chen, Mi-Feng; Cai, Kun; Synthetic Communications; vol. 27; nb. 6; (1997); p. 953 - 956 View in Reaxys

86 %

With C23H23ClN3RuSe2 (1+)*F6P(1-), 4-methylmorpholine N-oxide in dichloromethane, Reflux Das, Dipanwita; Singh, Pradhumn; Prakash, Om; Singh, Ajai K.; Inorganic Chemistry Communications; vol. 13; nb. 11; (2010); p. 1370 - 1373 View in Reaxys

85 %

With 1-oxo-4-methoxy-2,2,6,6-tetramethylpiperidinium chloride in dichloromethane, Time= 1h, Ambient temperature Yamaguchi; Takata; Endo; Bulletin of the Chemical Society of Japan; vol. 63; nb. 3; (1990); p. 947 - 949 View in Reaxys

85 %

With ammonium chlorochromate, silica gel in cyclohexane, Time= 3h, T= 60 °C Zhang, Gui-Sheng; Shi, Qi-Zeng; Chen, Mi-Feng; Cai, Kun; Synthetic Communications; vol. 27; nb. 21; (1997); p. 3691 - 3696 View in Reaxys

85 %

With iron(II) perchlorate monohydrate, ozone, acetonitrile Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1629 - 1637 View in Reaxys

85 %

With titanium(IV) oxide, oxygen, Time= 24h, T= 29.84 °C , p= 760.051Torr , Sealed tube, Irradiation Vadakkekara, Raji; Biswas, Abul Kalam; Sahoo, Tapan; Pal, Provas; Ganguly, Bishwajit; Ghosh, Subhash Chandra; Panda, Asit Baran; Chemistry - An Asian Journal; vol. 11; nb. 21; (2016); p. 3084 - 3089 View in Reaxys

84 %

With sodium bromite in acetic acid, Time= 5h, Ambient temperature Kageyama, Toshifumi; Ueno, Yoshio; Okawara, Makoto; Synthesis; nb. 10; (1983); p. 815 - 816 View in Reaxys

84 %

With aluminum oxide, quinolinium monofluorochromate(VI) in hexane, Time= 4.5h, Ambient temperature Rajkumar, G. Abraham; Arabindoo, Banumathi; Murugesan; Synthetic Communications; vol. 29; nb. 12; (1999); p. 2105 - 2114 View in Reaxys

84 %

With manganese(III) acetylacetonate, acetonitrile in tetrachloromethane, Time= 3h, T= 200 °C Khusnutdinov; Schadneva; Baiguzina; Dzhemilev; Russian Chemical Bulletin; vol. 51; nb. 6; (2002); p. 1065 1067 View in Reaxys

84 %

With C77H60Cl2N4O4PRu2, 4-methylmorpholine N-oxide in dichloromethane, Time= 8h, Reflux Venkatachalam; Raja; Pandiarajan; Ramesh; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 71; nb. 3; (2008); p. 884 - 891 View in Reaxys

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84 %

With C17H16Cl2N3O2RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Catalytic behavior, Reagent/catalyst Pramanik, Ajoy Kumar; Mondal, Tapan Kumar; Inorganica Chimica Acta; vol. 411; (2014); p. 106 - 112 View in Reaxys

84 %

General procedure for the oxidation General procedure: A mixture of benzhydrol (1 mmol, 0.184 g), isobutyraldehyde (1.5 mmol, 0.108 g), and catalyst (1 mol percent 0.01 mmol) in acetonitrile (15 mL) was heated at 60 °C under stirring by using an oxygen balloon. The progress of the reaction was monitored by thin layer chromatography on silica gel. On completion, the reaction mixture was cooled to room temperature and centrifuged to separate the catalyst. The product was identified with GCMS. The solvent was removed under reduced pressure and the product was obtained by passing it through a short column of silica gel using EtOAc–hexane (1:9) as eluent. The identity of the product was confirmed by comparing the physical and spectral data (1H and 13C NMR) with the reported compound. The recovered catalyst was dried at 50 °C for 2 h and can be reused for recycling experiments. With oxygen, isovaleraldehyde in acetonitrile, Time= 3.5h, T= 65 °C , Catalytic behavior Panwar, Vineeta; Kumar, Pawan; Ray, Siddharth S.; Jain, Suman L.; Tetrahedron Letters; vol. 56; nb. 25; (2015); p. 3948 - 3953 View in Reaxys

83 %

With potassium hexafluorophosphate, tert.-butylnitrite, 9-azabicyclo[3.3.1]nonane-N-oxyl, oxygen in water, Time= 3.5h, T= 60 °C , p= 3750.38Torr , Autoclave, Green chemistry Ma, Jiaqi; Hong, Chao; Wan, Yan; Li, Meichao; Hu, Xinquan; Mo, Weimin; Hu, Baoxiang; Sun, Nan; Jin, Liqun; Shen, Zhenlu; Tetrahedron Letters; vol. 58; nb. 7; (2017); p. 652 - 657 View in Reaxys

81 %

With isocyanate de chlorosulfonyle, dimethyl sulfoxide, triethylamine in dichloromethane, 1.) -78 deg C, 1.5 h, 2.) room temperature, 0.5 h Olah, George A.; Vankar, Yashwant D.; Arvanaghi, Massoud; Synthesis; nb. 2; (1980); p. 141 - 142 View in Reaxys

81 %

With (tetrabutylammonium)4[Al4(H2O)10(β-SbW9O33H)2]*4H2O, dihydrogen peroxide in water, acetonitrile, Time= 1h, T= 70 °C , Catalytic behavior, Reagent/catalyst Carraro, Mauro; Bassil, Bassem S.; Soraru, Antonio; Berardi, Serena; Suchopar, Andreas; Kortz, Ulrich; Bonchio, Marcella; Chemical Communications; vol. 49; nb. 72; (2013); p. 7914 - 7916 View in Reaxys

80 %

With sodium bromate, sodium dihydrogenphosphate, iron(III) chloride in water, acetonitrile, Time= 4h, T= 25 °C Shaabani; Ajabi; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 40; nb. 2; (2001); p. 148 - 151 View in Reaxys

80 %

With oxygen in water, Time= 12h, T= 60 °C , p= 760.051Torr Yamada, Yoichi M.A.; Arakawa, Takayasu; Hocke, Heiko; Uozumi, Yasuhiro; Chemistry - An Asian Journal; vol. 4; nb. 7; (2009); p. 1092 - 1098 View in Reaxys

78 %

With dihydrogen peroxide in water, acetone, Time= 19h, T= 56 °C , chemoselective reaction Kikukawa, Yuji; Yamaguchi, Kazuya; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 49; nb. 35; (2010); p. 6096 - 6100 View in Reaxys

77 %

With air, ferric(III) bromide, ferric nitrate in acetonitrile, Time= 24h, T= 20 °C Martin, Sandra E; Suarez, Dario F; Tetrahedron Letters; vol. 43; nb. 25; (2002); p. 4475 - 4479 View in Reaxys

75 %

With Amberlite IRA-120, urea-hydrogen peroxide, 1-n-butyl-3-methylimidazolim bromide, Time= 4h, T= 70 °C

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Bhati, Nishi; Sarma, Kuladip; Goswami, Amrit; Chemistry Letters; vol. 37; nb. 5; (2008); p. 496 - 497 View in Reaxys 74 %

With oxygen, Time= 16h, electrolysis: Hg cathode, plazinum foil anode, n-Bu4N(1+)*ClO4 (1-) / DMF, -1.0 V vs SCE Singh, Manorama; Misra, Ram A.; Synthesis; nb. 5; (1989); p. 403 - 404 View in Reaxys

71.0 %

With 3-chloro-benzenecarboperoxoic acid, (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride in dichloromethane, acetonitrile, Time= 0.166667h, T= 20 °C Han, Jung Hee; Yoo, Sang-Kun; Seo, Jin Soo; Hong, Sung Jin; Kim, Seok Kyu; Kim, Cheal; Dalton Transactions; nb. 2; (2005); p. 402 - 406 View in Reaxys

70 %

With dihydrogen peroxide, [Me(n-C8H17)3N]HSO4, sodium tungstate in water, Time= 16h, T= 90 °C , Oxidation Sato, Kazuhiko; Aoki, Masao; Takagi, Junko; Zimmermann, Klaus; Noyori, Ryoji; Bulletin of the Chemical Society of Japan; vol. 72; nb. 10; (1999); p. 2287 - 2306 View in Reaxys

70 %

With potassium hydroxide, cobalt(II) phthalocyanine, oxygen in xylene, Time= 15h, Heating Sharma, Vishal B.; Jain, Suman L.; Sain, Bir; Tetrahedron Letters; vol. 44; nb. 2; (2003); p. 383 - 386 View in Reaxys

70 %

With dihydrogen peroxide, methyltrioxorhenium(VII), sodium bromide in various solvent(s), Time= 6h, T= 20 °C Jain, Suman L.; Sharma, Vishal B.; Sain, Bir; Bulletin of the Chemical Society of Japan; vol. 79; nb. 10; (2006); p. 1601 - 1603 View in Reaxys

68%

General procedure: A solution of complex 1 (0.01mmol) in CH2Cl2 (25mL) was added to the mixture containing PhCH2OH (1mmol), NMO (3mmol) and molecular sieves. The reaction mixture was refluxed and conversion of PhCH2OH to PhCHO was monitored taking the reaction mixture at 10min time interval. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was then extracted with diethyl ether, concentrated to ≈1mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP–5 column of 30m length, 0.53mm diameter and 5.00μm film thickness. The column, injector and detector temperatures were 200, 250 and 250°C respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30mL/min. The injection volume of sample was 2μL. The oxidation products were identified by GC co-injection with authentic samples. No significant conversion was observed after 50min. All other alcohols were oxidized by refluxing the reaction mixture for 1h and conversions were monitored following the identical protocol. With C16H12Cl2N2O3RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 1h, T= 4 °C , Molecular sieve, Reflux Roy, Puspendu; Mondal, Apurba Sau; Pramanik, Ajoy Kumar; Mondal, Tapan Kumar; Journal of Organometallic Chemistry; vol. 828; (2017); p. 1 - 9 View in Reaxys

67 %

Stage 1: With potassium permanganate in acetone, Reflux Stage 2: With hydrogenchloride in water Zheng, Min-Yan; Wei, Yong-Sheng; Fan, Guang; Huang, Yi; Asian Journal of Chemistry; vol. 24; nb. 1; (2012); p. 161 - 164 View in Reaxys

65 %

With aluminum oxide, dimethylammonium chlorochromate in cyclohexane, Time= 3h, T= 55 - 60 °C Zhang, Gui-Sheng; Shi, Qi-Zeng; Chen, Mi-Feng; Cai, Kun; Organic Preparations and Procedures International; vol. 30; nb. 2; (1998); p. 215 - 218 View in Reaxys

65 %

General procedure for the oxidation of alcohols General procedure: A vial was charged with alcohol (1 mmol), IBX (1.2 mmol, 1.2 equiv) and 2 wt percent GMPGS-2000/H2O solution (5 mL). The mixture was stirred for 24 h at 25 °C and filtered. The solid was washed with

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CH2Cl2 and the filtrate was extracted with CH2Cl2 (3×10 mL). Then, the organic phase was combined and dried with anhydrous Na2SO4, evaporated to dryness. The crude product was purified was purified by column chromatography on silica gel eluted with (petroleum ether/EtOAc) to afford the desired product. With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water, Time= 24h, T= 25 °C , Micellar solution Xie, Aming; Zhou, Xiangxiang; Feng, Liandong; Hu, Xinyu; Dong, Wei; Tetrahedron; vol. 70; nb. 21; (2014); p. 3514 - 3519 View in Reaxys 64 %

With 30percent peracetic acid, resin-PPh2-Ru(PPh3)2Cl2 in ethyl acetate, 1,2-dichloro-ethane, Time= 2h, Heating Leadbeater; Journal of Organic Chemistry; vol. 66; nb. 6; (2001); p. 2168 - 2170 View in Reaxys

64 %

With [MnIII(2-((2-(2-(2-(2-hydroxybenzylideneamino)phenylamino)propylamino)phenylimino)methyl)phenolato)]Cl, dihydrogen peroxide in acetonitrile, Time= 3.3h, Reflux Azadbakht, Reza; Amini Manesh, Abbas; Malayeri, Mahdieh; Dehghani, Behzad; New Journal of Chemistry; vol. 39; nb. 8; (2015); p. 6459 - 6464 View in Reaxys

54 %

With pyridine, C22H16CoN2O8, oxygen in water, Time= 7h, T= 80 °C , pH= 11.5 Seyedi, Seyed Mohammad; Sandaroos, Reza; Zohuri, Gholam Hossein; Chinese Chemical Letters; vol. 21; nb. 11; (2010); p. 1303 - 1306 View in Reaxys

54 %

With pyridine-2-carbaldehyde, 2-(Aminomethyl)pyridine, iron(II) trifluoromethanesulfonate acetonitrile disolvate, dihydrogen peroxide in acetonitrile, Time= 1.5h, T= 25 °C Olivo, Giorgio; Giosia, Simone; Barbieri, Alessia; Lanzalunga, Osvaldo; Di Stefano, Stefano; Organic and Biomolecular Chemistry; vol. 14; nb. 45; (2016); p. 10630 - 10635 View in Reaxys

51 %

Optimized cyclohexanol oxidation with Aliquat 336 General procedure: Cyclohexanol (1.04 mL, 10 mmol, 1 equiv.), tungstic acid(58.9 mg, 0.24 mmol, 2.4 molpercent), Aliquat 336 (275 mg, 0.68 mmol,6.8 molpercent) and 30percent hydrogen peroxide (2.04 mL, 20 mmol, 2 equiv.)were introduced into a glass tube. The mixture was stirred at90 C for 30 min. Then, the organic phase was extracted withethyl acetate (3×2 mL) and cyclohexane (2×2 mL). The combinedorganic phases were dried with MgSO4 and analysed bygas chromatography (GC). The same procedure was used from theother substrates: cyclopentanol (0.91 mL, 10 mmol, 1 equiv.), cycloheptanol(1.20 mL, 10 mmol, 1 equiv.) and cyclooctanol (1.32 mL,10 mmol, 1 equiv.). With dihydrogen peroxide, ortho-tungstic acid, 1-octyl-3-methylimidazolium bis(trifluoromethanesulfonyl)amide in water, Time= 1h, T= 90 °C , Green chemistry Chatel, Gregory; Monnier, Camille; Kardos, Nathalie; Voiron, Celine; Andrioletti, Bruno; Draye, Micheline; Applied Catalysis A: General; vol. 478; (2014); p. 157 - 164 View in Reaxys

50.2 %

2 :(Silicon oxide)-based catalyst (copper oxide 67 mass percent, silicon 27 mass percent, sodium oxide 2 mass percent, and other metal oxides) were added to a stainless steel reaction tube (inner diameter 9.3 mm, length 100 mm) and E35S, manufactured by NittoKasei Chemical Industry Co., Ltd.), and the mixture was heated in an oven to 190 °C. Next, the reduction catalyst was subjected to reduction treatment in the reaction tube First, the vaporized cyclopentanol (purity of 99.2percent) was supplied from the inlet of the reaction tube at a rate of LHSV = 3.3 hr -1, and the reaction tube While the outlet pressure was maintained at atmospheric pressure, continuous reaction was carried out at 190 °C. In this case, since the reaction product flows out from the outlet of the reaction tube as a gas, it was cooled and collected to obtain a condensate (crude product). The condensate collected during 50 to 51 hours after the start of the continuous reaction was analyzed by gas chromatograph and the conversion rate of cyclopentanol, the selectivity of cyclopentanone, the yield of cyclopentanone. With copper oxide-silica catalyst (copper oxide 49 mass percent, 47 mass percent of silica, 1 mass percent of alumina, 2 mass percent of sodium oxide and 1 mass percent of other metal oxides), T= 190 °C , Reagent/catalyst

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Patent; ZEON CORPORATION; NAKANO, YASUSHI; (9 pag.); JP5790103; (2015); (B2) Japanese View in Reaxys 48 %

With C16H13MnNO3*3H2O, dihydrogen peroxide in water, Time= 1h, T= 20 °C , Ionic liquid Rong, Meizhu; Wang, Juan; Shen, Yanping; Han, Jinyu; Catalysis Communications; vol. 20; (2012); p. 51 - 53 View in Reaxys

47 %

With dihydrogen peroxide in water, acetonitrile, Time= 4h, T= 80 °C , chemoselective reaction Stolle, Achim; Ondruschka, Bernd; Morgenthal, Ingrid; Andersen, Olaf; Bonrath, Werner; Journal of Molecular Catalysis A: Chemical; vol. 335; nb. 1-2; (2011); p. 228 - 235 View in Reaxys

45 %

With oxygen, benzaldehyde in 1,2-dichloro-ethane, Time= 36h, T= 80 °C Choudary, Boyapati M.; Sudha, Yepuri; Synthetic Communications; vol. 26; nb. 9; (1996); p. 1651 - 1655 View in Reaxys

43%

With dihydrogen peroxide in acetone, Time= 20h, T= 24.84 °C , Inert atmosphere, Schlenk technique Xiang, Jing; Li, Hao; Wu, Jia-Shou; Zeitschrift fur Anorganische und Allgemeine Chemie; vol. 640; nb. 8-9; (2014); p. 1670 - 1674 View in Reaxys

39.5 %

With C56H45N4O3OsP2 (1+)*ClO4 (1-), 4-methylmorpholine N-oxide in dichloromethane, Time= 4h, Reflux, Molecular sieve, Catalytic behavior, Reagent/catalyst Datta, Papia; Sardar, Dibakar; Panda, Uttam; Halder, Ajanta; Manik, Nabin Baran; Chen, Chun-Jung; Sinha, Chittaranjan; Applied Organometallic Chemistry; vol. 30; nb. 5; (2016); p. 323 - 334 View in Reaxys

37 %

With tetrahexylammonium chloride, dihydrogen peroxide, lt;NBu4gt;lt;(Ph2PO2)(WO(O2)2)2gt; in benzene, Time= 3h, T= 75 °C , other new heteropolyperoxometalate catalysts and oxidation of various primary and secondary alcohols investigated Gresley, N. Melanie; Griffith, William P.; Parkin, Bernardeta C.; White, Andrew J. P.; Williams, David J.; Journal of the Chemical Society - Dalton Transactions; nb. 10; (1996); p. 2039 - 2045 View in Reaxys

32.1 %

With sodium ferrate(VI) in water, Time= 3h Tandon, Praveen K.; Singh, Santosh B.; Singh, Satpal; Kesarwani, Bhawana; Journal of the Indian Chemical Society; vol. 89; nb. 10; (2012); p. 1363 - 1367 View in Reaxys

31 %

With dihydrogen peroxide, lt;NMe4gt;3lt;(MePO3)lt;MePO2(OH)gt;W6O13(O2)4(OH)2(OH2)gt;*4H2O, Time= 3h, T= 70 °C Griffith, William P.; Parkin, Bernardeta C.; White, Andrew J. P.; Williams, David J.; Journal of the Chemical Society, Chemical Communications; nb. 21; (1995); p. 2183 - 2184 View in Reaxys

26 %

With boron trifluoride diethyl etherate, pyCo(TPP)NO2, Time= 1h Tovrog,Benjamin S.; Diamond, Steven E.; Mares, Frank; Szalkiewicz, Andrew; Journal of the American Chemical Society; vol. 103; nb. 12; (1981); p. 3522 - 3526 View in Reaxys

15 %

With Bis(7-methyl-10-(n-octyl)pyridodipyrimidin-3-yl)decane, Time= 25h, T= 115 °C Yoneda, Fumio; Tanaka, Kiyoshi; Yamato, Hirotake; Moriyama, Kenji; Nagamatsu, Tomohisa; Journal of the American Chemical Society; vol. 111; nb. 20; (1989); p. 9199 - 9202 View in Reaxys

10.5 %

With oxygen, 3,7-dimethyl-10-n-propylpyrimidolt;5,4-ggt;pteridine-2,4,6,8(3H,7H,9H,10H)-tetrone, Time= 25h, T= 120 °C

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Nagamatsu, Tomohisa; Matsumoto, Etsuko; Yoneda, Fumio; Chemistry Letters; (1982); p. 1127 - 1130 View in Reaxys 10.5 %

With oxygen, 3,7-dimethyl-10-n-propylpyrimidolt;5,4-ggt;pteridine-2,4,6,8(3H,7H,9H,10H)-tetrone, Time= 25h, T= 120 °C , further 10-substituted pyrimido<5,4-g>pteridinetetrones as oxidation catalysts, Product distribution Nagamatsu, Tomohisa; Matsumoto, Etsuko; Yoneda, Fumio; Chemistry Letters; (1982); p. 1127 - 1130 View in Reaxys

9.4 %

With C42H60N6O4 (1c), Time= 25h, T= 80 °C , Irradiation, different 1,3,8,10,11,14-hexapentaphene-2,4,7,9(14H,3H, 8H,11H)-tetraones and photosenzitizers, Product distribution Yoneda, Fumio; Koga, Masakazu; Ibuka, Toshiro; Yano, Yumihiko; Chemical & Pharmaceutical Bulletin; vol. 34; nb. 6; (1986); p. 2653 - 2655 View in Reaxys

2.5 %

With different mixed flavins, Time= 25h, T= 80 °C , sunlight, Product distribution Yoneda; Koga; Journal of Heterocyclic Chemistry; vol. 25; nb. 2; (1988); p. 549 - 553 View in Reaxys With chromium(VI) oxide, sulfuric acid Demjanow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 42; (1910); p. 840; Chem. Zentralbl.; vol. 81; nb. II; (1910); p. 1749 View in Reaxys

50 % Chromat.

With tert.-butylhydroperoxide, bis(acetylacetonate)oxovanadium in benzene, Time= 6h, T= 80 °C Kaneda, Kiyotomi; Kawanishi, Yasuyuki; Jitsukawa, Koichiro; Teranishi, Shiichiro; Tetrahedron Letters; vol. 24; nb. 45; (1983); p. 5009 - 5010 View in Reaxys With allyl methyl carbonate, dihydridotetrakis(triphenylphosphine)ruthenium(II) in toluene, Heating, Yield given Minami, Ichiro; Yamada, Mitsuru; Tsuji, Jiro; Tetrahedron Letters; vol. 27; nb. 16; (1986); p. 1805 - 1808 View in Reaxys

96 % Chromat.

With lt;MoO(O2)2C5H4N(O)COOgt;Bu4N in 1,2-dichloro-ethane, Time= 9h, T= 50 °C Bortolini, O.; Campestrini, S.; Furia, F. Di; Modena, G.; Valle, G.; Journal of Organic Chemistry; vol. 52; nb. 24; (1987); p. 5467 - 5469 View in Reaxys With oxygen, dihydrogen hexachloroplatinate, copper dichloride, Time= 18.5h, Ambient temperature, Irradiation, Yield given Cameron, Randy E.; Bocarsly, Andrew B.; Journal of the American Chemical Society; vol. 107; nb. 21; (1985); p. 6116 - 6117 View in Reaxys

94.3 % Chromat.

With tris(triphenylphosphine)ruthenium(II) chloride, potassium carbonate, acetophenone, acetone, Time= 1h, T= 56 °C Wang, G-Z.; Baeckvall, Jan-E.; Journal of the Chemical Society, Chemical Communications; nb. 4; (1992); p. 337 339 View in Reaxys

97 % Chromat.

With bis(quinuclidine)bromine(I) bromide, pyridinium trifluroacetate in dichloromethane, water, Time= 3h, Ambient temperature Blair, Larry K.; Hobbs, Steven; Bagnoli, Nicholas; Husband, Leslie; Badika, Ndofunsu; Journal of Organic Chemistry; vol. 57; nb. 5; (1992); p. 1600 - 1603 View in Reaxys

70 % Chromat.

With manganese(IV) oxide, potassium carbonate, [(η6-p-MeC6H4Pri)2Ru2Cl2(μ-Cl)2], 2,6-Di-tert-butyl-1,4-benzoquinone in tetrahydrofuran, Time= 20h, T= 65 °C

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Karlsson, Ulrika; Wang, Guo-Zhi; Baeckvall, Jan-E.; Journal of Organic Chemistry; vol. 59; nb. 5; (1994); p. 1196 - 1198 View in Reaxys in water, Time= 120h, T= 30 °C , culture medium containing Corynebacterium equi IFO 3730, Yield given Ohta, Hiromichi; Fujiwara, Hidenori; Tsuchihashi, Gen-ichi; Agricultural and Biological Chemistry; vol. 48; nb. 2; (1984); p. 317 - 322 View in Reaxys 93 % Chromat.

With silver tetrafluoroborate, bis(quinuclidine)bromine(I) tetrafluoroborate in dichloromethane, Time= 0.166667h Blair, Larry K.; Parris, Kevin D.; Lee, On Fai Daniel; Jenkins, Karen F.; Feese, Robin Chaney; et al.; Journal of Organic Chemistry; vol. 51; nb. 26; (1986); p. 5454 - 5456 View in Reaxys

68 % Chromat.

With tert.-butylhydroperoxide, cetyltrimethylammonium chlorochromate in benzene, Time= 2h, T= 80 °C Agarwal, D. D.; Kaul, Anju; Raina, Daisy; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 34; nb. 2; (1995); p. 158 - 160 View in Reaxys With tert.-butylhydroperoxide, 3 A molecular sieve, Zr(OR)x, silica gel in tetrachloromethane, dichloromethane, Time= 5h, T= 80 °C , other catalyst: Zr(O-n-Pr)4 Krohn, Karsten; Vinke, Ingeborg; Adam, Horst; Journal of Organic Chemistry; vol. 61; nb. 4; (1996); p. 1467 1472 View in Reaxys

72 % Chromat.

With dihydrogen peroxide, (cetylpyridinium)8CeW10O36 in chloroform, Time= 16h, T= 61 °C Shiozaki; Kominami; Kera; Synthetic Communications; vol. 26; nb. 9; (1996); p. 1663 - 1668 View in Reaxys

81 % Turn- With fluorine in acetonitrile ov. Chambers, Richard D.; Hutchinson, John; Sandford, Graham; Shah, Aneela; Vaughan, Julian F. S.; Tetrahedron; vol. 53; nb. 46; (1997); p. 15833 - 15842 View in Reaxys T= 50 °C , secondary alcohol dehydrogenase (SADH) from Thermoanaerobacter ethanolicus, NADP, Tris*HCl buffer, Rate constant Pham; Phillips; Journal of the American Chemical Society; vol. 112; nb. 9; (1990); p. 3629 - 3632 View in Reaxys With allyl methyl carbonate, dihydridotetrakis(triphenylphosphine)ruthenium(II), effect of other catalysts and reagents were examined., Product distribution, Mechanism Minami, Ichiro; Yamada, Mitsuru; Tsuji, Jiro; Tetrahedron Letters; vol. 27; nb. 16; (1986); p. 1805 - 1808 View in Reaxys With 3,10-dimethyl-8-dimethylaminopyrimidolt;4,5-bgt;quinoline-2(3H),4(10H)-dione, Time= 25h, T= 120 °C , other 5-deazaflavins, Product distribution Yoneda, Fumio; Mori, Kenya; Sakuma, Yoshiharu; Koshiro, Akira; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 945 - 947 View in Reaxys With enzyme of Nicotiana tabacum in water, Time= 2h, T= 25 °C , correlation of the reaction rate with 13C NMR, Rate constant, Equilibrium constant Suga, Takayuki; Izumi, Shunsuke; Hirata, Toshifumi; Chemistry Letters; (1986); p. 2053 - 2056 View in Reaxys With nicotinamide adenine dinucleotide, horse liver alcohol dehydrogenase in various solvent(s), T= 25 °C , pH 9, Rate constant

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Jones, J. Bryan; Schwartz, Harold M.; Canadian Journal of Chemistry; vol. 59; (1981); p. 1574 - 1579 View in Reaxys With ditellurato cuprate(III), ruthenium trichloride, T= 31.9 °C , in alkaline medium, Kinetics, Rate constant Bal Reddy, K.; Sethuram, B.; Navaneeth Rao, T.; Bulletin des Societes Chimiques Belges; vol. 90; nb. 10; (1981); p. 1017 - 1022 View in Reaxys With perchloric acid, oxochromium(IV), lithium perchlorate in water, T= 25 °C , Rate constant Scott, Susannah L.; Bakac, Andreja; Espenson, James H.; Journal of the American Chemical Society; vol. 114; nb. 11; (1992); p. 4205 - 4213 View in Reaxys With oxygen, dihydrogen hexachloroplatinate, copper dichloride, Time= 18.5h, Ambient temperature, Irradiation, various alcohols, various times, Mechanism, Quantum yield Cameron, Randy E.; Bocarsly, Andrew B.; Journal of the American Chemical Society; vol. 107; nb. 21; (1985); p. 6116 - 6117 View in Reaxys With barium permanganate, hydroxide in water, T= 34.9 °C , various temperatures, different reagent concentrations; Ea, ΔH(excit.), ΔS(excit.), Kinetics, Thermodynamic data, Mechanism Pati, Subas C.; Dev, B. R.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 21; nb. 2; (1982); p. 165 - 167 View in Reaxys With lt;Ag(OH)2(H4TeO6)2gt;(3-), hydroxide, T= 26.9 °C , ΔE(excit.), ΔG(excit.), ΔH(excit.), ΔS(excit.), Thermodynamic data, Mechanism, Kinetics Ravi Prasad, T.; Sethuram, B.; Navaneeth Rao, T.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 21; nb. 2; (1982); p. 170 - 171 View in Reaxys With potassium hydroxide, Cu(OH)2(H4TeO6), tellurate, T= 9.4 °C , other temperatures and concentrations, catalysis by OsO4, Kinetics, Mechanism Reddy, K. Bal; Murthy, C. P.; Sethuram, B.; Navaneeth Rao, T.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 20; nb. 3; (1981); p. 272 - 275 View in Reaxys With ruthenium trichloride, perchloric acid, mercury(II) diacetate, bromate in water, T= 60 °C , other temperatures and solvent; ΔE, ΔH and ΔS(excit.), Kinetics, Mechanism, Thermodynamic data Radhakrishnamurti, P. S.; Sarangi, L. D.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 20; nb. 3; (1981); p. 301 - 303 View in Reaxys With sulfuric acid, mercury(II) diacetate, saccharin in water, acetic acid, T= 45 °C , var. concn. of substrate, saccharin, sulphuric acid, Mechanism, Thermodynamic data, Rate constant Mohan, K. Vijaya; Rao, P. Raghunath; Sundaram, E. V.; Journal of the Indian Chemical Society; vol. 61; nb. 10; (1984); p. 876 - 879 View in Reaxys With N-chlorosaccharin, sulfuric acid in water, acetic acid, T= 44.9 °C , effect of N-chlorosaccharin concentration; effect of cycloalkanol concentration; effect of acid concentration; effect of solvent composition; ΔE, ΔH(act.), ΔS(act.), ΔG(act.), Kinetics, Thermodynamic data, Equilibrium constant Mohan, K. Vijaya; Rao, P. Raghunatha; Sundaram, E. V.; Journal of the Indian Chemical Society; vol. 63; (1986); p. 698 - 700 View in Reaxys With bromamine T in perchloric acid, T= 35 °C , mechanism; effect of concentrations, ionic strength and solvent composition; solvent isotope effect, Rate constant, Kinetics, Thermodynamic data

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Singh, Bharat; Singh, A. K.; Journal of the Indian Chemical Society; vol. 62; nb. 7; (1985); p. 523 - 525 View in Reaxys With lt;MoO(O2)2(C5H4NOCOO)gt;-Bu4N+ in 1,2-dichloro-ethane, T= 50 °C , Rate constant Campestrini, Sandro; Di Furia, Fulvio; Tetrahedron; vol. 50; nb. 17; (1994); p. 5119 - 5130 View in Reaxys With 12-butyl-3-methyl-14-octyl-9-phenyl-3,9-dihydro-1,3,9,11,12,14-hexazapentacene-2,4,8,10-tetraone, Time= 24h, T= 10 - 15 °C , Irradiation, var. of reagent, temp., Product distribution Yoneda, Fumio; Kuroda, Kazunori; Koga, Masakazu; Ibuka, Toshiro; Journal of the Chemical Society, Chemical Communications; nb. 13; (1984); p. 872 - 873 View in Reaxys With sodium hydroxide, NAD, glycine, Time= 2h, T= 25 °C , Equilibrium constant, Rate constant Izumi, Shunsuke; Suga, Takayuki; Bulletin of the Chemical Society of Japan; vol. 61; nb. 5; (1988); p. 1715 - 1720 View in Reaxys With dipotassium peroxodisulfate, silver nitrate in water, T= 35 °C , further temperatures; also K2SO4; Ea, ΔG(excit.), ΔH(excit.), ΔS(excit.), various concentrations of cyclopentanol and reagent, Rate constant, Thermodynamic data, Mechanism Srivastava, S. P.; Gupta, V. K.; Sharma, R. G.; Singh, B. P.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 20; nb. 12; (1981); p. 1221 - 1223 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, hypochlorite, sodium bromide in water, T= 1.5 °C , pH 10; with/without TEMPO, Rate constant De Nooy; De Nooy, Arjan E. J.; Besemer; Besemer, Arie C.; Van Bekkum; Van Bekkum, Herman; Tetrahedron; vol. 51; nb. 29; (1995); p. 8023 - 8032 View in Reaxys With tert.-butylhydroperoxide, 3 A molecular sieve, zircornium(IV) n-propoxide in tetrachloromethane, Time= 3.5h, T= 20 °C , initial reaction rate, 50percent conversion reaction time, other primary and secondary alcohols, other catalysts, other solvents, other reaction temperatures and times, Mechanism Krohn, Karsten; Vinke, Ingeborg; Adam, Horst; Journal of Organic Chemistry; vol. 61; nb. 4; (1996); p. 1467 1472 View in Reaxys With sulfuric acid, quinolinium dichromate(VI) in N,N-dimethyl-formamide, T= 49.9 °C , var. temp, var. catalyst; ΔH(excit.), ΔS(excit.), ΔG(excit.), Rate constant, Thermodynamic data Nongkynrih, Irona; Mahanti, Mahendra K.; Bulletin of the Chemical Society of Japan; vol. 69; nb. 5; (1996); p. 1403 - 1407 View in Reaxys With chromium(VI) oxide, sodium dodecyl-sulfate in water, T= 35 °C , ΔH(excit.), -ΔS(excit.); var. temperature, Rate constant, Thermodynamic data Sahu; Panigrahi; Journal of the Indian Chemical Society; vol. 73; nb. 11; (1996); p. 576 - 579 View in Reaxys 90 % Chromat.

With air, cryptomelan H-K-OMS-2 in toluene, Time= 4h, T= 110 °C Son, Young-Chan; Makwana, Vinit D.; Howell, Amy R.; Suib, Steven L.; Angewandte Chemie - International Edition; vol. 40; nb. 22; (2001); p. 4280 - 4283 View in Reaxys With cis-[Os(VIII)O4(OH)2](2-), [Fe(CN)6](3-), acetonitrile, Time= 2h, T= 20 °C Griffith; Suriaatmaja; Canadian Journal of Chemistry; vol. 79; nb. 5-6; (2001); p. 598 - 606 View in Reaxys

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100 % Spectr.

With pentamethylcyclopentadienyliridium dichloride, potassium carbonate in acetone, Time= 6h, T= 20 °C Fujita, Ken-Ichi; Furukawa, Shigetoyo; Yamaguchi, Ryohei; Journal of Organometalic Chemistry; vol. 649; nb. 2; (2002); p. 289 - 292 View in Reaxys With cyclic alcohol dehydrogenase from Gluconobacter frateurii, T= 25 °C , pH= 5.0, Enzyme kinetics Moonmangmee; Fujii; Toyama; Theeragool; Lotong; Matsushita; Adachi; Bioscience, biotechnology, and biochemistry; vol. 65; nb. 12; (2001); p. 2763 - 2772 View in Reaxys

99 % Chromat.

With mukaiyama’s reagent, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 0.5h, T= 20 °C 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 whole cells of Rhodococcus ruber DSM 44541, acetone in phosphate buffer, T= 24 °C , pH= 8.0, Oppenauer oxidation Stampfer, Wolfgang; Kosjek, Birgit; Moitzi, Christian; Kroutil, Wolfgang; Faber, Kurt; Angewandte Chemie (International ed. in English); vol. 41; nb. 6; (2002); p. 1014 - 1017 View in Reaxys

96 % Chromat.

With sodium hypochlorite, sodium hydrogencarbonate, potassium bromide, TEMPO-linked 5,10,15,20-tetraphenylMn-porphyrin in dichloromethane, Time= 0.5h, T= 0 °C , pH= 8.6 Huang, Jian-Ying; Li, Shi-Jun; Wang, Yan-Guang; Tetrahedron Letters; vol. 47; nb. 32; (2006); p. 5637 - 5640 View in Reaxys With potassium bromate, perchloric acid, mercury(II) diacetate, iridium(III) chloride, T= 34.85 °C , Kinetics, Further Variations: Temperatures Srivastava, Sheila; Sharma, Rajendra Kumar; Singh, Sarika; Journal of the Indian Chemical Society; vol. 83; nb. 3; (2006); p. 282 - 287 View in Reaxys With perchloric acid, mercury(II) diacetate, N-bromoacetamide, ruthenium trichloride in water, Time= 48h, T= 35 °C , Kinetics, Further Variations: Temperatures, Reagents Srivastava, Sheila; Awasthi, Ajaya; Singh, Kulina; International Journal of Chemical Kinetics; vol. 37; nb. 5; (2005); p. 275 - 281 View in Reaxys With 2,6-dichloropyridine N-oxide, EDMA, Ru(II)(CO)(meso-(4-vinylC6H4)4-porphyrinate), hydrogen bromide in benzene, Time= 3h, T= 55 °C , Product distribution, Further Variations: Reagents Nestler, Oliver; Severin, Kay; Organic Letters; vol. 3; nb. 24; (2001); p. 3907 - 3909 View in Reaxys With oxygen, aluminum oxide, ruthenium in various solvent(s), Time= 8h, T= 82.84 °C Yamaguchi, Kazuya; Mizuno, Noritaka; Chemistry - A European Journal; vol. 9; nb. 18; (2003); p. 4353 - 4361 View in Reaxys

84 % Chromat.

With oxygen, hydroxyapatite-bound Pd in various solvent(s), Time= 24h, T= 90 °C Mori, Kohsuke; Yamaguchi, Kazuya; Hara, Takayoshi; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi; Journal of the American Chemical Society; vol. 124; nb. 39; (2002); p. 11572 - 11573 View in Reaxys

92 % Chromat.

With dihydrogen peroxide, [MoO(O2)2(TEDA)2] in water, Time= 8h, T= 80 °C Luan, Yi; Wang, Ge; Luck, Rudy L.; Yang, Mu; Han, Xiao; Chemistry Letters; vol. 36; nb. 10; (2007); p. 1236 1237

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View in Reaxys 20 : Example 20 The same procedures as in Example 17 were repeated except that cyclopentanol was used as a substrate in place of cyclohexanol. The conversion of cyclopentanol was 92percent, and the selectivity to cyclopentanone was more than 99percent. With oxygen in 2,3,4-trifluorotoluene, Time= 8h, T= 20 - 83 °C , Conversion of starting material Patent; Mizuno, Noritaka; Yamaguchi, Kazuya; Ishida, Hajime; US2004/204597; (2004); (A1) English View in Reaxys 97.1 % Chromat.

With oxygen, Pt-GLY in water, Time= 24h, T= 80 °C , p= 760.051Torr Wang, Tao; Xiao, Chao-Xian; Yan, Liang; Xu, Lin; Luo, Jie; Shou, Heng; Kou, Yuan; Liu, Haichao; Chemical Communications; nb. 42; (2007); p. 4375 - 4377 View in Reaxys With oxygen in toluene, Time= 24h, T= 79.84 °C , p= 760.051Torr Wang, Feng; Ueda, Wataru; Chemistry Letters; vol. 37; nb. 2; (2008); p. 184 - 185 View in Reaxys

90 %Chromat.

With α,α,α-trifluorotoluene, oxygen in water, Time= 115h, T= 20 °C Miyamura, Hiroyuki; Matsubara, Ryosuke; Kobayashi, Shu; Chemical Communications; nb. 17; (2008); p. 2031 2033 View in Reaxys

57 %Chromat.

With α,α,α-trifluorotoluene, water, oxygen, potassium carbonate, Time= 48h, T= 30 °C , p= 760.051Torr , Kinetics, Time Lucchesi, Celine; Inasaki, Takeshi; Miyamura, Hiroyuki; Matsubara, Ryosuke; Kobayashi, Shu; Advanced Synthesis and Catalysis; vol. 350; nb. 13; (2008); p. 1996 - 2000 View in Reaxys With 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Singh, Pradhumn; Singh, Monika; Singh, Ajai K.; Journal of Organometallic Chemistry; vol. 694; nb. 24; (2009); p. 3872 - 3880 View in Reaxys

95 %Chromat.

With NaAuCl4, oxygen, caesium carbonate in toluene, Time= 30h, T= 30 °C , p= 760.051Torr Karimi, Babak; Kabiri Esfahani, Farhad; Chemical Communications; nb. 37; (2009); p. 5555 - 5557 View in Reaxys With Oxonereg;, tetrabutylammomium bromide in water, Time= 1h, T= 20 °C , Irradiation Wu, Shang; Ma, Hengchang; Yan, Penghua; Wang, Jianqiang; Ding, Juanjuan; Lei, Ziqiang; Letters in Organic Chemistry; vol. 6; nb. 5; (2009); p. 424 - 427 View in Reaxys With potassium bromate, rhodium(III) chloride, potassium chloride, mercury(II) diacetate, sodium hydroxide in water, T= 35 °C , Kinetics, Temperature Srivastava, Sheila; Srivastava, Parul; Chaudhary, Lakshmi; Kumar, Ashish; Singh, Shalini; Journal of the Indian Chemical Society; vol. 86; nb. 1; (2009); p. 58 - 62 View in Reaxys

70 %Chromat.

2-1 :Example 2-1 A mixture of 1 mmol of cyclopentanol, 5 mL of toluene, and 0.1 g of the catalyst prepared from Example 2-0 and including Ag particles immobilized on a hydrotalcite surface was stirred at 110° C. in an argon atmosphere for 24 hours and thereby yielded a corresponding carbonyl compound (cyclopentanone) in a yield equivalent to a gas chromatographic (GC) yield of 70percent, with a selectivity for chclopentanone of 99percent or more. With Ag/HT in toluene, Time= 24h, T= 110 °C , Inert atmosphere

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Patent; Kaneda, Kiyotomi; Yamasaki, Noritsugu; US2010/130758; (2010); (A1) English View in Reaxys With [ruthenium(II)chloride(.eta.6-p-cymene)(1-(4-methoxyphenyltelluromethyl)-1H-benzotriazole)](hexaflourophosphate), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Das, Dipanwita; Singh, Pradhumn; Singh, Ajai K.; Journal of Organometallic Chemistry; vol. 695; nb. 7; (2010); p. 955 - 962 View in Reaxys 85 %Chromat.

With NiZn-Pd(0.02) nanocomposite catalyst in α,α,α-trifluorotoluene, Time= 12h, T= 99.84 °C , p= 760.051Torr Hara, Takayoshi; Ishikawa, Masakazu; Sawada, Junya; Ichikuni, Nobuyuki; Shimazu, Shogo; Green Chemistry; vol. 11; nb. 12; (2009); p. 2034 - 2040 View in Reaxys With oxygen in water, Time= 3h, T= 85 °C , p= 750.075Torr Yang, Xiaomin; Wang, Xiuna; Qiu, Jieshan; Applied Catalysis A: General; vol. 382; nb. 1; (2010); p. 131 - 137 View in Reaxys

100 With dihydrogen peroxide in water, Time= 8h, T= 89.84 °C %Chromat. Ma, Baochun; Zhang, Yingshuai; Ding, Yong; Zhao, Wei; Catalysis Communications; vol. 11; nb. 9; (2010); p. 853 - 857 View in Reaxys With (TSPP)Rh(III)(H2O)2, oxygen, sodium hydroxide in water, T= 80 °C , p= 760.051Torr Liu, Lianghui; Yu, Mengmeng; Wayland, Bradford B.; Fu, Xuefeng; Chemical Communications; vol. 46; nb. 34; (2010); p. 6353 - 6355 View in Reaxys With C22H23NRuSSe(2+)*2F6P(1-), 4-methylmorpholine N-oxide in dichloromethane, Time= 2h, Reflux Singh, Pradhumn; Das, Dipanwita; Singh, Monika; Singh, Ajai K.; Inorganic Chemistry Communications; vol. 13; nb. 2; (2010); p. 223 - 226 View in Reaxys With oxygen in water, Time= 12h, T= 60 °C Ma, Zhancheng; Yang, Hengquan; Qin, Yong; Hao, Yajuan; Li, Guang; Journal of Molecular Catalysis A: Chemical; vol. 331; nb. 1-2; (2010); p. 78 - 85 View in Reaxys With C52H43N3O4P2RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Ulaganatha Raja; Gowri; Ramesh; Polyhedron; vol. 29; nb. 3; (2010); p. 1175 - 1181 View in Reaxys 100 With oxygen in α,α,α-trifluorotoluene, water, Time= 24h, T= 20 °C , p= 760.051Torr %Chromat. Kaizuka, Kosuke; Miyamura, Hiroyuki; Kobayashi, Shu; Journal of the American Chemical Society; vol. 132; nb. 43; (2010); p. 15096 - 15098 View in Reaxys 93 %Chromat.

With hydrotalcite-supported gold nanoparticles (Au/HT), air in toluene, Time= 36h, T= 40 °C , p= 760.051Torr Mitsudome, Takato; Noujima, Akifumi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Advanced Synthesis and Catalysis; vol. 351; nb. 11-12; (2009); p. 1890 - 1896 View in Reaxys With dihydrogen peroxide, acetic acid, sodium bromide in water, Time= 4h, T= 60 °C Qi, Xingyi; Wang, Jing; Zheng, Liwei; Qi, Lin; Synlett; nb. 4; (2011); p. 555 - 558; Art.No: W17410ST View in Reaxys With dihydrogen peroxide in 1,4-dioxane, water, Time= 7h, T= 85 °C

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Ding, Yong; Zhao, Wei; Journal of Molecular Catalysis A: Chemical; vol. 337; nb. 1-2; (2011); p. 45 - 51 View in Reaxys With [ruthenium(II)chloride(.eta.6-benzene)(N-[2-(phenylseleno)ethyl]morpholine)](hexafluorophosphate), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Singh, Pradhumn; Singh, Ajai K.; European Journal of Inorganic Chemistry; nb. 26; (2010); p. 4187 - 4195 View in Reaxys With oxygen in toluene, Time= 3h, T= 80 °C , p= 760.051Torr Yamaguchi, Kazuya; Kim, Jung Won; He, Jinling; Mizuno, Noritaka; Journal of Catalysis; vol. 268; nb. 2; (2009); p. 343 - 349 View in Reaxys Stage 1: With potassium hydride in acetonitrile Stage 2: With 4-acetylamino-2,2,6,6-tetramethyl-piperidine-1-oxoam-monium perchlorate in acetonitrile, Time= 3h, T= 20 °C Zhu, Xiao-Qing; Chen, Xi; Mei, Lian-Rui; Organic Letters; vol. 13; nb. 9; (2011); p. 2456 - 2459 View in Reaxys With dihydrogen peroxide in water, Time= 0.833333h, Microwave irradiation Carraro, Mauro; Nsouli, Nadeen; Oelrich, Holger; Sartorel, Andrea; Soraru, Antonio; Mal, Sib Sankar; Scorrano, Gianfranco; Walder, Lorenz; Kortz, Ulrich; Bonchio, Marcella; Chemistry - A European Journal; vol. 17; nb. 30; (2011); p. 8371 - 8378 View in Reaxys With dihydrogen peroxide in water, Time= 1h, T= 90 °C Xie, Ting; Lu, Min; Zhang, Wenwen; Li, Jun; Journal of Chemical Research; vol. 35; nb. 7; (2011); p. 397 - 399 View in Reaxys 35 %Chromat.

With periodic acid in water, Time= 24h, T= 27 °C , chemoselective reaction Babu, S. Ganesh; Priyadarsini, P. Aruna; Karvembu; Applied Catalysis A: General; vol. 392; nb. 1-2; (2011); p. 218 - 224 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, Time= 24h, T= 89.84 °C Gao, Yongjun; Ma, Ding; Hu, Gang; Zhai, Peng; Bao, Xinhe; Zhu, Bo; Zhang, Bingsen; Su, Dang Sheng; Angewandte Chemie - International Edition; vol. 50; nb. 43; (2011); p. 10236 - 10240 View in Reaxys With dihydrogen peroxide in water, Time= 8h, T= 84.84 °C Zhao, Wei; Ding, Yong; Ma, Baochun; Qiu, Wenyuan; Synthetic Communications; vol. 42; nb. 4; (2012); p. 554 562 View in Reaxys

87 %Chromat.

With oxygen, potassium carbonate in α,α,α-trifluorotoluene, Time= 10h, T= 95 °C Karimi, Babak; Elhamifar, Dawood; Clark, James H.; Hunt, Andrew J.; Organic and Biomolecular Chemistry; vol. 9; nb. 21; (2011); p. 7420 - 7426 View in Reaxys

93 %Chromat.

With C51H51ClN2O2P2RuS, 4-methylmorpholine N-oxide in acetonitrile, Time= 12h, T= 27 °C Gunasekaran; Remya; Radhakrishnan; Karvembu; Journal of Coordination Chemistry; vol. 64; nb. 3; (2011); p. 491 - 501 View in Reaxys With 2C2H6O*C38H26CoN6S2 (2+)*H2O*2NO3 (1-), dihydrogen peroxide in water, Time= 8h, T= 20 °C , chemoselective reaction

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Nemati Kharat, Ali; Bakhoda, Abolghasem; Tamaddoni Jahromi, Bahareh; Polyhedron; vol. 30; nb. 17; (2011); p. 2768 - 2775 View in Reaxys 86 %Spectr.

With potassium carbonate in acetone, Time= 8h, T= 65 °C , Kinetics, Reagent/catalyst Terashima, Takaya; Ouchi, Makoto; Ando, Tsuyoshi; Sawamoto, Mitsuo; Journal of Polymer Science, Part A: Polymer Chemistry; vol. 49; nb. 5; (2011); p. 1061 - 1069 View in Reaxys

90 %Chromat.

With tert.-butylhydroperoxide, [Co(III)(N-(dibenzylcarbamothioyl)benzamide(-H))3] in acetonitrile, Time= 30h, T= 80 °C Gunasekaran; Jerome; Ng, Seik Weng; Tiekink, Edward R.T.; Karvembu; Journal of Molecular Catalysis A: Chemical; vol. 353-354; (2012); p. 156 - 162 View in Reaxys With sodium chlorite, cis-[Ru(2,9-dimethyl-1,10-phenanthroline)2(OH2)2]2+, T= 22.84 °C , pH= 6.8, aq. phosphate buffer Hu, Zongmin; Du, Hongxia; Man, Wai-Lun; Leung, Chi-Fai; Liang, Haojun; Lau, Tai-Chu; Chemical Communications; vol. 48; nb. 8; (2012); p. 1102 - 1104 View in Reaxys 2.6. Catalytic oxidation General procedure: Catalytic oxidation of primary alcohols to the corresponding aldehydes and secondary alcohols to ketones by ruthenium(II) carbonyl complexes was studied in the presence of NMO as co-oxidant. A typical reaction using the complex [Ru(η6-p-cymene)(AsPh3)(L4)] (4) as a catalyst and primary or secondary alcohol as substrates at a 1:100 M ratio is described as follows. A solution of ruthenium complex (4) (0.01 mmol) in 20 cm3 CH2Cl2 was added to the solution of substrate (1 mmol) and NMO (3 mmol). The solution mixture was refluxed for 3-10 h and the solvent was then evaporated from the mother liquor under reduced pressure. The residue was then extracted with diethyl ether (20 cm3) and was analyzed by GC and 1H NMR. The oxidized products were determined by GC and 1H NMR by comparison with authentic samples and no internal standards were used. With Ru[(.eta.6-p-cumene)(AsPh3)(C5H4NC(S)NC6H2(CH3)3)]BPh4, 4-methylmorpholine N-oxide in dichloromethane, Time= 10h, T= 40 °C Raja, M. Ulaganatha; Ramesh; Journal of Organometallic Chemistry; vol. 699; (2012); p. 5 - 11 View in Reaxys

88 %Chromat.

2.5. Catalytic oxidation of alcohols General procedure: To a solution of alcohol (1 mmol) in dichloromethane (20 mL),ruthenium(II) complex (1 molpercent) and NMO (351 mg; 3 mmol) were added. The mixture was stirred at 27 °C for 12 h. Then the solution was concentrated and the alcohol and aldehyde/ketone were obtained by passing the solution through a short silica gel column (hexane/ethyl acetate). The extract was then analyzed by GC. With [Ru(S(C6H4)NCH(C6H4)O(Br))(CO)(PPh3)2], 4-methylmorpholine N-oxide in dichloromethane, Time= 12h, T= 27 °C Muthu Tamizh; Mereiter; Kirchner; Karvembu; Journal of Organometallic Chemistry; vol. 700; (2012); p. 194 201 View in Reaxys

86 %Chromat.

With [Cp*Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)](OTf)2 in water, tert-butyl alcohol, Time= 20h, Inert atmosphere, Reflux Kawahara, Ryoko; Fujita, Ken-Ichi; Yamaguchi, Ryohei; Journal of the American Chemical Society; vol. 134; nb. 8; (2012); p. 3643 - 3646 View in Reaxys With oxygen, benzaldehyde, Time= 16h, T= 110 °C , Neat (no solvent) Kuang, Yongbo; Nabae, Yuta; Hayakawa, Teruaki; Kakimoto, Masa-Aki; Applied Catalysis A: General; vol. 423-424; (2012); p. 52 - 58 View in Reaxys

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95 %Chromat.

With oxygen, caesium carbonate in toluene, Time= 24h, T= 20 °C Karimi, Babak; Esfahani, Farhad Kabiri; Advanced Synthesis and Catalysis; vol. 354; nb. 7; (2012); p. 1319 1326 View in Reaxys

76 %Chromat.

With 3-(3-(1,2-dicarboxyethylamino)-3-oxopropyl)-1-methyl-1H-imidazol-3-ium bromide, dihydrogen peroxide, Time= 1.33333h, T= 25 °C , Neat (no solvent) Karthikeyan, Parasuraman; Arunrao, Aswar Sachin; Narayan, Muskawar Prashant; Kumar, Sythana Suresh; Kumar, S. Senthil; Bhagat, Pundlik Rambhau; Journal of Molecular Liquids; vol. 173; (2012); p. 180 - 183 View in Reaxys

86 %Chromat.

3.4 Procedure for catalytic oxidation of alcohols General procedure: Catalytic oxidation of primary alcohol to corresponding aldehyde and secondary alcohol to ketone by ruthenium(II) complexes were studied in the presence of NMO, H2O2 or ButOOH as co-oxidant. A typical reaction using the complex as a catalyst and primary or secondary alcohol, as substrate at 1:100 molar ratio was described as follows. A solution of [Ru(CO)2Cl2(α-NaiEt)] (1b) (0.01 mmol) in CH2Cl2 (20 ml) was added to the mixture containing PhCH2OH (1 mmol), NMO (3 mmol) and molecular sieves. The reaction mixture was refluxed for 1 h, and the solvent was then evaporated under reduced pressure. The residue was then extracted with diethyl ether (20 ml), concentrated to ≈1 ml and was analyzed by GC. The oxidation products were identified by GC co-injection with authentic samples. All other alcohols were oxidized following identical reaction protocol. With C17H14Cl2N4O2Ru, 4-methylmorpholine N-oxide in dichloromethane, Time= 1h, Molecular sieve, Reflux Sarkar, Shyamal Kumar; Jana, Mahendra Sekhar; Mondal, Tapan Kumar; Sinha, Chittaranjan; Journal of Organometallic Chemistry; vol. 716; (2012); p. 129 - 137 View in Reaxys With H4N(1+)*Zn2Sb2, dihydrogen peroxide in water, Time= 7h, T= 85 °C Ni, Lubin; Patzke, Greta R.; Patscheider, Joerg; Baldridge, Kim K.; Chemistry--A European Journal; vol. 18; nb. 42; (2012); p. 13293 - 13298,6 View in Reaxys Ni, Lubin; Patscheider, Joerg; Baldridge, Kim K.; Patzke, Greta R.; Chemistry - A European Journal; vol. 18; nb. 42; (2012); p. 13293 - 13298 View in Reaxys

98 %Chromat.

With [bis(acetoxy)iodo]benzene, [Al(OH)(bpydc)·0.07RuCl3(DMSO)·0.5H2O] in dichloromethane, Time= 3.5h, T= 40 °C , Sealed tube, Catalytic behavior Carson, Fabian; Agrawal, Santosh; Gustafsson, Mikaela; Bartoszewicz, Agnieszka; Moraga, Francisca; Zou, Xiaodong; Martin-Matute, Belen; Chemistry - A European Journal; vol. 18; nb. 48; (2012); p. 15337 - 15344 View in Reaxys With 2O34W9Zn(12-)*24H2O*10H4N(1+)*4Zn(2+)*2Sb(3+), dihydrogen peroxide in water, Time= 7h, T= 85 °C , Reagent/ catalyst Ni, Lubin; Patscheider, Joerg; Baldridge, Kim K.; Patzke, Greta R.; Chemistry - A European Journal; vol. 18; nb. 42; (2012); p. 13293 - 13298 View in Reaxys With O32W10 (4-)*4C9H14N(1+), dihydrogen peroxide in water, Time= 8h, T= 80 °C Liu, Dan; Gui, Jianzhou; Lu, Feng; Sun, Zhaolin; Park, Yong-Ki; Catalysis Letters; vol. 142; nb. 11; (2012); p. 1330 - 1335 View in Reaxys

100 With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in hexane, Time= 20h, T= 120 °C , Solvent %Chromat. Kawahara, Ryoko; Fujita, Ken-Ichi; Yamaguchi, Ryohei; Angewandte Chemie - International Edition; vol. 51; nb. 51; (2012); p. 12790 - 12794; Angew. Chem.; (2012); p. 12962 - 12966 View in Reaxys Stage 1: in dichloromethane, Time= 0.05h, T= 10 °C , Sonication

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Stage 2: With sodium hypochlorite, sodium bromide in dichloromethane, water, Time= 0.116667h, T= 10 °C , pH= 9.1 Zheng, Zhi; Wang, Jianli; Zhang, Miao; Xu, Lixin; Ji, Jianbing; ChemCatChem; vol. 5; nb. 1; (2013); p. 307 - 312 View in Reaxys With dihydrogen peroxide in water, Time= 7h, T= 90 °C , Reflux Zhang, Zhenxin; Zhu, Qianqian; Ding, Yong; Synthetic Communications; vol. 43; nb. 9; (2013); p. 1211 - 1218 View in Reaxys 4.7 Procedure for catalytic oxidation of alcohols General procedure: Catalytic oxidation of primary alcohol to corresponding aldehyde and secondary alcohol to ketone by ruthenium(II) complexes were studied in the presence of NMO as cooxidant. A typical reaction using the complex as a catalyst and primary or secondary alcohol, as substrate at 1:100 molar ratio was described as follows. A solution of [Ru(CO)2(L)Cl2] (1) (0.01 mmol) in CH2Cl2 (25 mL) was added to the mixture containing PhCH2OH (1 mmol), NMO (3 mmol) and molecular sieves. The reaction mixture was refluxed for 2 h, and the solvent was then evaporated under reduced pressure. The residue was then extracted with diethyl ether (20 mL), concentrated to ≈1 mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30 m length, 0.53 mm diameter and 5.00 μm film thickness. The column, injector and detector temperatures were 200, 250 and 250 °C, respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30 mL/min. The injection volume of sample was 2 mL. The oxidation products were identified by GC co injection with authentic samples. All other alcohols were oxidized following identical reaction protocol. With C11H7I2N3O2RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 2h, T= 400 °C , Molecular sieve, Reagent/catalyst Kundu, Subhankar; Sarkar, Deblina; Jana, Mahendra Sekhar; Pramanik, Ajoy Kumar; Jana, Subrata; Mondal, Tapan Kumar; Journal of Molecular Structure; vol. 1035; (2013); p. 277 - 284 View in Reaxys 94 %Chromat.

3.4. Procedure for catalytic oxidation General procedure: Catalytic oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones respectively by ruthenium(II) and osmium(II) carbonyl iodide complexes were studied in the presence of NMO as a co-oxidant and the byproduct, water, was removed by using about 0.5 g of molecular sieves. Typical reactions were carried out using the ruthenium and osmium complexes as the catalyst and benzyl alcohol, 2-butanol, cyclopentanol and cyclohexanol as substrates in a 1:100 molar ratio. Solutions of the ruthenium and osmium complexes (0.01 mmol) in 20 cm3 CH2Cl2 were added to a solution of the substrate (1 mmol) and NMO (3 mmol). The solution mixture was refluxed for 2 h and the solvent was then evaporated from the mother liquor under reduced pressure. The residue was then extracted with petroleum ether (20 cm3) and was analyzed by GC using an Agilent 7890 series Gas chromatography instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30 m length, 0.53 mm diameter and 5.00 lm film thickness. The ether extracts were evaporated to give the corresponding aldehydes/ketones, which were then isolated and quantified as their 2,4-dinitrophenylhydrazone derivatives. With trans-(Cl)-[Ru(CO)2Cl2(1-ethyl-2-(phenylazo)imidazole)], 4-methylmorpholine N-oxide in dichloromethane, Time= 2h, Reflux, Molecular sieve, Reagent/catalyst Sarkar, Shyamal Kumar; Jana, Mahendra Sekhar; Mondal, Tapan Kumar; Sinha, Chittaranjan; Polyhedron; vol. 50; nb. 1; (2013); p. 246 - 254 View in Reaxys

99 %Chromat.

With sodium bromate, cis-[Ru(2,9-Me2phen)2(OH2)2](PF6)2 in water, Time= 10h, T= 23 °C Hu, Zongmin; Ma, Li; Xie, Jianhui; Du, Hongxia; Lam, William W. Y.; Lau, Tai-Chu; New Journal of Chemistry; vol. 37; nb. 6; (2013); p. 1707 - 1710 View in Reaxys

94.4 With tert.-butylhydroperoxide, Cu(9-(2'-hydroxy-3'-phenylthio-5'-tert-butylphenyl)-6-methylthio-3-acetyl-5,7,8-triaza%Chromat. nona-3,6,8-trien-2-one(2-)) in water, Time= 4h, T= 80 °C , Microwave irradiation, Reagent/catalyst Arion, Vladimir B.; Platzer, Sonja; Rapta, Peter; Machata, Peter; Breza, Martin; Vegh, Daniel; Dunsch, Lothar; Telser, Joshua; Shova, Sergiu; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Inorganic Chemistry; vol. 52; nb. 13; (2013); p. 7524 - 7540 View in Reaxys

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91 %Chromat.

Procedures for catalytic oxidation General procedure: The oxidation reaction was done in the following procedure:187 mg of the reduced 2 wtpercent Ir/TiO2 (Ir: 20 mol, 1.25 molpercent tosubstrates), the solvent (toluene or mesitylene, 1.5 mL), and thesubstrate (1.5 mmol) were charged into a glass vial (17 mL). Thereaction was started by stirring the reaction mixture at 353 K inalcohol oxidation or 423 K in xanthene oxidation under molecularoxygen at atmospheric pressure. The products were identified by comparison of the mass and NMR spectra with those of authenticsamples. The yields of the products were determined using GCanalyses with an internal standard technique. With oxygen in toluene, Time= 3h, T= 79.84 °C , p= 760.051Torr Yoshida, Akihiro; Mori, Yoshinori; Ikeda, Tsuyoshi; Azemoto, Kazuki; Naito, Shuichi; Catalysis Today; vol. 203; (2013); p. 153 - 157 View in Reaxys With [ruthenium(II)(η6-benzene)(chloride)(NC5H4CH2SC6H5)](hexafluorophosphate), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Reagent/catalyst, Time Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham Lal; Singh, Ajai K.; Dalton Transactions; vol. 42; nb. 24; (2013); p. 8736 - 8747 View in Reaxys With Pt#Bi2O3, oxygen in water, Time= 5h, T= 90 °C , p= 750.075Torr , Autoclave Lu, Tianliang; Du, Zhongtian; Liu, Junxia; Ma, Hong; Xu, Jie; Green Chemistry; vol. 15; nb. 8; (2013); p. 2215 2221 View in Reaxys

89.9 With ruthenium(III) chloride trihydrate, trichloroisocyanuric acid, tetrabutylammomium bromide, potassium carbonate %Chromat. in water, ethyl acetate, Time= 3h, T= 25 - 45 °C , Green chemistry Yamaoka, Hidenori; Moriya, Narimasa; Ikunaka, Masaya; Organic Process Research and Development; vol. 8; nb. 6; (2004); p. 931 - 938 View in Reaxys 80 %Chromat.

General procedure: All experiments were conducted in 50 cm3 glass reactor. A fourbladed–pitched turbine impeller was used for reaction. The temperature was maintained at the selected value. Weighed quantitiesof reactants and catalyst were charged to the reactor and then the temperature raised to the desired value. Thereafter the agitation was commenced. An initial sample was taken and further sampling was done periodically up to 4 h. A standard experiment was performed with 0.01 mol 1-phenylethanol, 0.03 mol TBHP and catalyst quantity of 0.012 g/cm3. The temperature was normally maintainedat 75°C at 900 rpm as speed of agitation. The total volume of liquidphase was 15.0 cm3in which 0.2 cm3 n-decane was used as internal standard. At the end of experiment, the catalyst was filtered and the organic layer was concentrated and purified by columnchromatography. With tert.-butylhydroperoxide in acetonitrile, T= 75 °C Yadav, Ganapati D.; Yadav, Akhilesh R.; Journal of Molecular Catalysis A: Chemical; vol. 380; (2013); p. 70 - 77 View in Reaxys Procedure for catalytic oxidation of alcohols General procedure: Catalytic oxidation of primary alcohols to corresponding aldehydes and secondary alcohols to ketones by ruthenium(II) complexes were studied in the presence of NMO as co-oxidant. A typical reaction using the complex as a catalyst and primary or secondary alcohol, as substrate at 1:100 M ratio was described as follows. A solution of complex 1 (0.01 mmol) in CH2Cl2 (25 mL) wasadded to the mixture containing PhCH2OH (1 mmol), NMO(3 mmol) and molecular sieves. The reaction mixture was refluxedand conversion of PhCH2OH to PhCHO was monitored taking the reaction mixture at 10 min time interval. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was then extracted with diethyl ether, concentrated to 1 mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30 mlength, 0.53 mm diameter and 5.00 lm film thickness. The column,injector and detector temperatures were 200, 250 and 250 C respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30 mL/min. The injection volume of sample was 2 lL. The oxidation products were identified by GC co-injection with authentic samples. No significant conversion was observed after 50 min. Allother alcohols were oxidized by refluxing the reaction mixture for 1 h and conversions were monitored following the identical protocol.

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With C14H14I2N2O4RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 1h, T= 40 °C , Molecular sieve, Reagent/catalyst Jana, Subrata; Jana, Mahendra Sekhar; Sarkar, Deblina; Paira, Mrinal Kanti; Mondal, Tapan Kumar; Journal of Molecular Structure; vol. 1054-1055; (2013); p. 83 - 88 View in Reaxys 80 %Chromat.

With periodic acid in water, Time= 12h, T= 45 °C Ganesamoorthy; Muthu Tamizh; Shanmugasundaram; Karvembu; Tetrahedron Letters; vol. 54; nb. 51; (2013); p. 7035 - 7039 View in Reaxys With lyophilised cells of Escherichia coli overexpressing the solvent-tolerant alcohol dehydrogenase from Rhodococcus ruber DSM44541 in aq. buffer, Time= 24h, T= 30 °C , pH= 7.5, Resolution of racemate, Enzymatic reaction Paul, Caroline E.; Lavandera, Ivan; Gotor-Fernandez, Vicente; Kroutil, Wolfgang; Gotor, Vicente; ChemCatChem; vol. 5; nb. 12; (2013); p. 3875 - 3881 View in Reaxys With tert.-butylhydroperoxide, oxygen in neat (no solvent), Time= 24h, T= 90 °C , Catalytic behavior Narkhede, Nilesh; Patel, Anjali; Singh, Sukriti; Dalton Transactions; vol. 43; nb. 6; (2014); p. 2512 - 2520 View in Reaxys

77 %Chromat.

4.6 General procedure for Oppenauer oxidation General procedure: In a typical run, an oven-dried round bottom flask was charged with a known mole percent of catalyst, K2CO3 (1.7mmol), primary or secondary alcohol (1.0mmol) in acetone medium (8mL). The mixture was stirred at 40°C. After the specified time the reaction mixture was extracted with ether (4×10mL). The combined organic layer was washed with water (3×10mL), and dried over anhydrous Na2SO4. Solvent was removed under vacuum. The residue was dissolved in hexane and analyzed by GC–MS. With C49H43IrN2P2, potassium carbonate in acetone, Time= 4h, Oppenauer Oxidation, Reagent/catalyst Paul, Piyali; Richmond, Michael G.; Bhattacharya, Samaresh; Journal of Organometallic Chemistry; vol. 751; (2014); p. 760 - 768 View in Reaxys With tert.-butylhydroperoxide, Cs5[PCo(H2O)Mo11O39]*6H2O, oxygen, Time= 24h, T= 90 °C , Reagent/catalyst, chemoselective reaction Pathan, Soyeb; Patel, Anjali; Catalysis Science and Technology; vol. 4; nb. 3; (2014); p. 648 - 656 View in Reaxys Oxidation of other alcohols over Cr-13X General procedure: The catalytic oxidation of cyclohexanol (Scheme 1) was carriedout in a 25-mL single-necked round-bottom glass flask equipped with a cryogenic-liquid condenser under atmospheric pressure. In a typical run, 40.0 mmol of cyclohexanol, 10.0 mmol of TBHP,and 100 mg of the catalyst were added to the reactor, and the mixture was stirred vigorously by a magnetic stirrer and heated in a preheated water bath. After the completion of the reaction, the liquid products were separated by centrifugation and analyzed by a gas chromatograph equipped with a capillary column (SE-30, 30 m × 0.25 mm × 0.25 m) and an FID detector, in which chlorobenzene was used as an internal standard to quantify all the components, and the solid catalyst was separated by filtration and washed thoroughly with acetone and ethanol, and dried at 373 K overnight for the next use. The cyclohexanol conversion, cyclohexanone selectivity, TBHP conversion and TBHP efficiency werecalculated by using Eqs. (1)-(4). With tert.-butylhydroperoxide in neat (no solvent), Time= 7h, T= 89.84 °C , p= 760.051Torr , Green chemistry Li, Kun; Zhou, Dan; Deng, Jiejie; Lu, Xinhuan; Xia, Qinghua; Journal of Molecular Catalysis A: Chemical; vol. 387; (2014); p. 31 - 37 View in Reaxys With C24H29ClRhSe2 (1+)*F6P(1-), potassium carbonate, acetone in water, Time= 5h, T= 80 °C , Oppenauer Oxidation, Catalytic behavior, Reagent/catalyst

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Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham L.; Singh, Ajai K.; Organometallics; vol. 33; nb. 4; (2014); p. 983 - 993 View in Reaxys With [Ru(CO)(1-methyl-2-{(o-thiomethyl)phenylazo}imidazole)I2], 4-methylmorpholine N-oxide in dichloromethane, T= 40 °C , Molecular sieve, Reflux, Reagent/catalyst Jana, Subrata; Jana, Mahendra Sekhar; Biswas, Sujan; Sinha, Chittaranjan; Mondal, Tapan Kumar; Journal of Molecular Structure; vol. 1065-1066; nb. 1; (2014); p. 52 - 60 View in Reaxys 83 %Chromat.

With dihydrogen peroxide in water, Time= 12h, T= 80 °C Shokouhimehr, Mohammadreza; Shin, Keun-Young; Lee, James S.; Hackett, Michael J.; Jun, Samuel Woojoo; Oh, Myoung Hwan; Jang, Jyongsik; Hyeon, Taeghwan; Journal of Materials Chemistry A; vol. 2; nb. 20; (2014); p. 7593 - 7599 View in Reaxys in toluene, Time= 18h, T= 110 °C , Catalytic behavior Ganesh Babu; Krishnamoorthi; Thiruneelakandan; Karvembu; Catalysis Letters; vol. 144; nb. 7; (2014); p. 1245 - 1252 View in Reaxys Stage 1: in dichloromethane, Time= 0.00833333h, Sonication, Micellar solution Stage 2: With sodium hypochlorite, sodium bromide in dichloromethane, Time= 0.1h, T= 10 °C , pH= Ca. 9.1, Micellar solution Zheng, Zhi; Wang, Jianli; Chen, Hualiang; Feng, Linbin; Jing, Ren; Lu, Meizhen; Hu, Bao; Ji, Jianbing; ChemCatChem; vol. 6; nb. 6; (2014); p. 1626 - 1634 View in Reaxys

70 %Chromat.

2.4. Aerial oxidation of alcohols General procedure: Five milligram of r-RuO2/MWCNT (0.68 molpercent) was stirred with3 mL of toluene taken in a round-bottomed flask equipped with a condenser and a magnetic stirrer. The substrate (1 mmol) was added to the stirring solution and then the mixture was refluxed at 110°C under atmospheric pressure of air. The completion of the reaction was checked by GC. After the reaction, the r-RuO2/MWCNTwas separated out from the reaction mixture by simple centrifugation and the products and unconverted reactants were analyzed by GC without any purification. Selectivity of the product for each reaction was also calculated. With air, multiwall carbon nanotube supported on r-ruthenium dioxide nanoparticle in toluene, Time= 20h, T= 110 °C Gopiraman; Babu, S. Ganesh; Karvembu; Kim; Applied Catalysis A: General; vol. 484; (2014); p. 84 - 96 View in Reaxys With 2O39PW11 (7-)*11K(1+)*Pr(3+)*22H2O, dihydrogen peroxide in water, Time= 3h, T= 90 °C , Green chemistry Saini, Mukesh Kumar; Gupta, Rakesh; Parbhakar, Swati; Singh, Surendra; Hussain, Firasat; RSC Advances; vol. 4; nb. 72; (2014); p. 38446 - 38449 View in Reaxys

93 %Chromat.

4.3. General procedure for catalytic aerobic oxidation of primaryalcohols in water General procedure: A mixture of magnetic nanoparticles 1a-e (suspension in ethanol; 0.16 M CoePd), primary alcohol (0.2 mmol), and potassium carbonate (0.2 mmol) in water (2 mL) was stirred at 60 C under oxygen gas at atmospheric pressure. After being cooled, the mixture was washed with ether, and acidified with 5percent hydrochloric acid. The mixture was extracted with ethyl acetate (51 mL). The extract was dried over magnesium sulfate. The resulting solution was analyzed by GC and GC-MS (with Mass Spectral Reference Database). The yield of the product was determined by GC with aninternal standard (o-xylene). With Co0.44Pd0.56, oxygen, potassium carbonate in ethanol, water, T= 60 °C , p= 760.051Torr Ito, Yoshikazu; Ohta, Hidetoshi; Yamada, Yoichi M.A.; Enoki, Toshiaki; Uozumi, Yasuhiro; Tetrahedron; nb. 36; (2014); p. 6146 - 6149 View in Reaxys

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> 99 General procedure for oxidation of alcohols to the correspondingcarbonyl compound with 30percent H2O2 %Chromat. General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5 mmol) were added to an equal mixture of water and acetonitrile (1.5 ml). Then, WO4PMO-IL (0.23 g, ~1.5 mol percent) was added to the above solution and the resulting mixture was stirred at 90 °C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (310 ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. With dihydrogen peroxide in water, acetonitrile, Time= 19h, T= 90 °C , Green chemistry Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; nb. 36; (2014); p. 6114 - 6119 View in Reaxys 77 %Chromat.

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], sodium acetate in water, acetic acid, toluene, Time= 24h, T= 100 °C Gunay, Ahmet; Mantell, Mark A.; Field, Kathleen D.; Wu, Wenbo; Chin, Michael; Emmert, Marion H.; Catalysis Science and Technology; vol. 5; nb. 2; (2015); p. 1198 - 1205 View in Reaxys With oxygen in toluene, Time= 20h, T= 60 °C , p= 760.051Torr , Catalytic behavior Zhang, Pengfei; Qiao, Zhen-An; Jiang, Xueguang; Veith, Gabriel M.; Dai, Sheng; Nano Letters; vol. 15; nb. 2; (2015); p. 823 - 828 View in Reaxys

>99 4.5 General procedure for oxidation of alcohols to the corresponding carbonyl compound with 30percent %Chromat. H2O2 General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5mmol) were added to an equal mixture of water and acetonitrile (1.5ml). Then, WO4 =PMO-IL (0.23g, ∼1.5 molpercent) was added to the above solution and the resulting mixture was stirred at 90°C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (3×10ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. With dihydrogen peroxide in water, acetonitrile, Time= 19h, T= 90 °C , Green chemistry, chemoselective reaction Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; vol. 70; nb. 36; (2014); p. 6114 - 6119 View in Reaxys 100 With dihydrogen peroxide in water, Time= 2.16667h, T= 45 °C , Green chemistry %Chromat. Nikbakht, Elham; Yadollahi, Bahram; Farsani, Mostafa Riahi; Inorganic Chemistry Communications; vol. 55; (2015); p. 135 - 138 View in Reaxys 93 %Chromat.

4.4. General procedure for catalytic aerobic oxidation of secondary alcohols in water General procedure: A mixture of magnetic nanoparticles 1a (suspension in ethanol) and secondary alcohol (0.2 mmol) in water (2 mL) was stirred at 60°C under oxygen gas at atmospheric pressure. After it was cooled, the mixture was extracted with ethyl acetate (51 mL). The extract was analyzed by GC and GC-MS (with Mass Spectral Reference Database). The yield of the product was determined by GC with an internal standard (o-xylene or mesitylene). With oxygen in water, Time= 24h, T= 60 °C , p= 760.051Torr

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Ito, Yoshikazu; Ohta, Hidetoshi; Yamada, Yoichi M.A.; Enoki, Toshiaki; Uozumi, Yasuhiro; Tetrahedron; vol. 70; nb. 36; (2014); p. 6146 - 6149 View in Reaxys With tert.-butylhydroperoxide, oxygen in water, Time= 24h, T= 90 °C , Catalytic behavior Singh, Sukriti; Narkhede, Nilesh; Patel, Anjali; RSC Advances; vol. 5; nb. 46; (2015); p. 36270 - 36278 View in Reaxys 81 %Chromat.

With potassium carbonate in water, Time= 5h, T= 80 °C Rostamnia, Sadegh; Doustkhah, Esmail; Karimi, Ziba; Amini, Soraya; Luque, Rafael; ChemCatChem; vol. 7; nb. 11; (2015); p. 1678 - 1683 View in Reaxys With methoxybenzene in toluene, Time= 24h, T= 100 °C Poreddy, Raju; Engelbrekt, Christian; Riisager, Anders; Catalysis Science and Technology; vol. 5; nb. 4; (2015); p. 2467 - 2477 View in Reaxys

80 %Chromat.

Typical procedure for catalytic oxidation of alcohols General procedure: The catalytic reactions were carried out in a 10-mL roundbottomflask equipped with a magnetic stirring bar and areflux condenser. The Co-STPOM catalyst (0.001 mmol),water (3 mL), alcohol (1 mmol), and H2O2 (9.8 mmol)were charged in the reaction vessel. The reaction was carriedout at reflux and progress of the reaction was detectedby TLC and GC. After completion of the reaction, organicproduct was isolated by ethyl acetate (3 × 2 mL) and theorganic layer was analyzed by gas chromatography or 1HNMR. Products were assigned by comparing experimentaldata with authentic samples. With 10Na(1+)*4Co(2+)*2O34PW9 (9-), dihydrogen peroxide in water, Time= 4h, Reflux, Green chemistry Farsani, Mostafa Riahi; Assady, Elham; Jalilian, Fariba; Yadollahi, Bahram; Rudbari, Hadi Amiri; Journal of the Iranian Chemical Society; vol. 12; nb. 7; (2015); p. 1207 - 1212; Art.No: 583 View in Reaxys

99 %Chromat.

With sodium periodate, C14H30Cl2FeN4 (1+)*F6P(1-) in water, Time= 22h, T= 23 °C Tan, Peng; Kwong, Hoi-Ki; Lau, Tai-Chu; Chemical Communications; vol. 51; nb. 61; (2015); p. 12189 - 12192 View in Reaxys in N,N-dimethyl-formamide, Time= 10h, T= 120 °C , Inert atmosphere Zhu, Yaoqin; Shen, Mengnan; Xia, Yonggen; Lu, Ming; Applied Organometallic Chemistry; vol. 29; nb. 3; (2015); p. 152 - 156 View in Reaxys With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-), urea hydrogen peroxide adduct in acetonitrile, Time= 12h, T= 70 °C Amanchi, Srinivasa Rao; Khenkin, Alexander M.; Diskin-Posner, Yael; Neumann, Ronny; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3336 - 3341 View in Reaxys With styrene, 1,3,5-trimethyl-benzene, Time= 24h, T= 130 °C , Inert atmosphere Lu, Tianliang; Du, Zhongtian; Liu, Junxia; Chen, Chen; Xu, Jie; Chinese Journal of Catalysis; vol. 35; nb. 12; (2014); p. 1911 - 1916 View in Reaxys 2.5. Procedure for catalytic oxidation of alcohols with NMO General procedure: A solution of complex (0.01 mmol) in CH2Cl2 (25 mL) was addedto the mixture containing alcohol substrate (1 mmol), K2CO3(1.3 mmol), solid NMO (3 mmol) and molecular sieves. The reactionmixture was refluxed for 3 h, and the solvent was then evaporatedunder reduced pressure. The residue was then extracted withdiethyl ether (20 mL), concentrated to z 1 mL. The oxidizedproduct present in diethyl ether extract was analyzed by GC.

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With C31H27Cl2N2PRhS(1+)*F6P(1-), potassium carbonate, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Molecular sieve, Reflux Biswas, Sujan; Sarkar, Deblina; Kundu, Subhankar; Roy, Puspendu; Mondal, Tapan Kumar; Journal of Molecular Structure; vol. 1099; (2015); p. 297 - 303 View in Reaxys 12 %Chromat.

2.4. Procedure for Alcohol Oxidation General procedure: A typical reaction scheme for the alcohol oxidation isgiven in Scheme 1. Au–MgO nanorods (30 mg) and H2O2(945 L, 15 equivalence) were stirred in 20 mL of waterand the substrate alcohol (1 mM) was slowly added to thereaction mixture and continuously stirred at room temperature.After the requisite time, the catalyst was separatedby centrifugation. The centrifugate was extracted usingdiethyl ether. The ether extract was dried over anhydroussodium sulphate and evaporated. Then the product was dissolvedin ethyl acetate and then analysed by GC. Authenticsamples of reactants and respective products were used toverify the retention time and to confirm the product formation.The used catalyst was washed with ethyl acetate and dried under vacuum. The dried catalyst was calcinedat 500 C before reuse. With dihydrogen peroxide in water, Time= 24h, T= 27 °C Emayavaramban; Ganesh Babu; Karvembu; Kadirvelu; Dharmaraj; Journal of Nanoscience and Nanotechnology; vol. 16; nb. 3; (2016); p. 2517 - 2526 View in Reaxys With air, hydrogen reduced 10 wtpercent alumina supported silver in para-xylene, Time= 3h, T= 120 °C Liu, Huihui; Tan, Hui-Ru; Tok, Eng Soon; Jaenicke, Stephan; Chuah, Gaik-Khuan; ChemCatChem; vol. 8; nb. 5; (2016); p. 968 - 975 View in Reaxys 2.3. General procedure of catalytic oxidation reaction General procedure: Oxidation of alcohol was carried out in a 100 mL three-neckedflask equipped with a reflux condenser, a magnetic stirrer anda thermometer. typically, the reactor was loaded with alcohol(5 mmol), H2O (10 mL) and catalyst. then, 30percent aqueous hydro-gen peroxide (10 mmol) was added dropwise to the reactorunder the setting temperature under vigorous stirring for 300 min.after the finish of reaction, the products were extracted withdichloromethane from aqueous phase and were identified by aSP-3420A GC equipped with a KB-Wax column (30 m, 0.32 mm id,0.25 m film thickness) with toluene as internal standardAlcoholconversion(percent)=[(molesofalcoholadded−molesofunconvertedalcohol)/molealcoholadded]×100Productselectivity(percent)=[molesoftheproduct/(molesofalcoholadded−molesofunconvertedalcohol)]×100TOF : mmolketone/(mmolheteropolyanionincatalyst×reactiontime). With dihydrogen peroxide in water, Time= 6h, T= 90 °C Wang, Hefang; Fang, Luping; Yang, Yongfang; Hu, Rongbin; Wang, Yanji; Applied Catalysis A: General; vol. 520; (2016); p. 35 - 43 View in Reaxys Oxidation of alcohols catalyzed by [Fe(N-N)3](OTf)2In General procedure: In a round-bottomed flask the solvent (3.0 mL) and the cat-alyst precursor [Fe(N-N)3] (OTf)2(0.050 mmol) were introduced, followed by the substrate (2.5 mmol). For reactions performed at temperatures higher than r.t., the resulting solution was heated ina thermostatted bath to the desired temperature. Slow addition of the oxidant was then carried out under stirring. After the desired time the reaction mixture was cooled at −18 °C and subsequently analized by GC and/or NMR. With tert.-butylhydroperoxide, [Fe(2,2'-bipyridine)3](OTf)2, Time= 24h, T= 25 °C , Green chemistry Chàvez, Jennifer E.; Crotti, Corrado; Zangrando, Ennio; Farnetti, Erica; Journal of Molecular Catalysis A: Chemical; vol. 421; (2016); p. 189 - 195 View in Reaxys

70.5 catalytic alcohol oxidations by t-BuOOH in the presence of iron complexes %Chromat. General procedure: t-BuOOH (0.075 mmol) was added to a mixture of substrate(0.05 mmol), iron complex (1.0 103 mmol), imidazole (0.01 mmol), NHPI (0.02 mmol), and solvent (CH3CN; 1 mL). The mixture was stirred for the given time at 50 °C. Each reaction was monitored by GC/MS analysis of 20 lL aliquots withdrawn periodically from the reaction mixture. Dodecane was used as an internal standard to quantify the yields of products and conversions of

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substrates. All reactions were run at least in triplicate, and the average conversions and product yields have been presented. Conversions and product yields were calculated with respect to substrates. With 1H-imidazole, tert.-butylhydroperoxide, N -hydroxyphthalimide, [Fe(bpc)Cl2][Et4N] in acetonitrile, Time= 7h, T= 50 °C , Reagent/catalyst Bae, Jeong Mi; Lee, Myoung Mi; Lee, Seul Ah; Lee, Sun Young; Bok, Kwon Hee; Kim, Jinheung; Kim, Cheal; Inorganica Chimica Acta; vol. 451; (2016); p. 8 - 15 View in Reaxys 47 %Spectr.

7 :A stock solution of KHSO5 was prepared in degassed D20 under N2. Catalyst (e.g., Co-dppe) was added to each reaction tube. The tubes were then evacuated under vacuum and refilled with N2 several times. 400 jtL of d5-acetone was added to each tube followed by the appropriate substrate. Reactions were initiated by the addition of 100 pL of KHSO5 stock solution. Reactions were monitored for 3 or 15 hrs depending on the substrate. The reactions were quenched by addition of a stock solution of d4-sodium trimethylsilyl propionate (NMR internal standard) and d5dim- ethylsulfoxide (oxidant quench). The reactions stirred another 15 mm and then were filtered into NMR tubes. The reactions were quantified by NMR. (Control reactions were performed without catalyst and in each case the substrate conversion is >5percent)10209] For most of the substrates selective oxidation to a single product was observed. The catalyst system was able to oxidize unactivated alkanes to a single product but in low yield. Oxidation of 1 -butanol illustrates the difference the catalyst and simple cobalt salts. The catalyst selectively oxidizes butanol to butyric acid whereas the CoOl) salts tested were highly unselective, affording several different products. With oxone in [(2)H6]acetone, Time= 15h, Inert atmosphere Patent; Yale University; Bloomfield, Aaron J.; Sheehan, Stafford W.; Collom, Samuel L.; Crabtree, Robert H.; Anastas, Paul T.; (31 pag.); US2016/152648; (2016); (A1) English View in Reaxys With oxygen in hexane, Time= 6h, T= 19.84 °C , p= 760.051Torr , Green chemistry Patent; Lee, Deok Rok; Kim, Jeong Won; (10 pag.); KR2016/9439; (2016); (A) Korean View in Reaxys Stage 1: With nickel(II) chloride hexahydrate, cadmium sulphide in acetonitrile, Time= 0.00277778h, Schlenk technique, Sonication, Inert atmosphere Stage 2: in acetonitrile, Time= 20h, T= 20 °C , Irradiation, Inert atmosphere, Schlenk technique Chai, Zhigang; Zeng, Ting-Ting; Li, Qi; Lu, Liang-Qiu; Xiao, Wen-Jing; Xu, Dongsheng; Journal of the American Chemical Society; vol. 138; nb. 32; (2016); p. 10128 - 10131 View in Reaxys

95 %Chromat.

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

78 %Chromat.

With tert.-butylhydroperoxide, C9H11CuN7O7S*H2O in water, Time= 0.25h, T= 80 °C , Microwave irradiation, Catalytic behavior, Reagent/catalyst Frija, Luís M.T.; Alegria, Elisabete C.B.A.; Sutradhar, Manas; Cristiano, M. Lurdes S.; Ismael, Amin; Kopylovich, Maximilian N.; Pombeiro, Armando J.L.; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 283 - 290 View in Reaxys

99 %Chromat.

With potassium carbonate in water, T= 80 °C , Catalytic behavior Vessally, Esmail; Ghasemisarabbadeih, Mostafa; Ekhteyari, Zeynab; Hosseinzadeh-Khanmiri, Rahim; Ghorbani-Kalhor, Ebrahim; Ejlali, Ladan; RSC Advances; vol. 6; nb. 108; (2016); p. 106769 - 106777 View in Reaxys 8 : Embodiment 8 The 0.86g Cyclopentaol, 2mol percent (relative to the Cyclopentaol) aza jin'gang alkane nitroxyl radical (II), 2mol percent (relative to the Cyclopentaol) vanadyl sulfate, 5 ml acetonitrile is added to the reactor, filled with oxygen

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pressure is 0.5 MPa, in the 80 °C running 3h after cooling to room temperature. Sampling by the use of gas chromatography analysis, Cyclopentaol conversion 99.8percent, dumasin selectivity of 97.4percent. With 1-methyl-2-azaadamantane-N-oxyl, oxovanadium(IV) sulfate, oxygen in acetonitrile, Time= 3h, T= 80 °C , p= 3750.38Torr Patent; Dalian University of Technology; Du, zhongtian; Tang, yangyang; Sun, xiaowan; (5 pag.); CN105541526; (2016); (A) Chinese View in Reaxys 7 :General procedure: The dehydrogenation reactor is a stainless steel tubular reactor of size Φ25ππΧ 1000mm. The reaction tube is filled with 100ml catalyst. The catalyst is composed of Ni and Cu as the active components, A mixture of Al230 and Si02 is a carrier having a Ni content of 30 to 50 wtpercent, a Cu content of 1 to 5 wtpercent The The bottom of the reactor is filled with inert porcelain balls. The dehydrogenated feedstock is preheated and passed through the distributor at a rate set at the top through the distributor into the reactor for dehydrogenation. The dehydrogenation material enters the gas stream from the bottom of the dehydrogenation reactor Separator, liquid phase material into the product tank. The system pressure is controlled by the gas regulator valve separated by the gasliquid separator. The specific reaction conditions, the dehydrogenation reaction of cyclopentanol conversion and cyclopentanone selectivity are shown in Table 1. With Ni-Cu/Al 2O3-SiO 2, T= 135 °C , p= 150.015Torr , Flow reactor, Temperature, Pressure Patent; Shanghai Pearlk Chemicals Co., Ltd; Shi, Kangming; (5 pag.); CN105461526; (2016); (A) Chinese View in Reaxys 100 12 : Synthesis of ketone by dehydrogenative oxidation reaction of secondary alcohol %Chromat. Dehydrogenative oxidation reactions of various secondary alcohols were carried out using complex 1 as a catalyst under the reaction conditions shown in Table 3. After the reactions were completed, when the reaction solutions were analyzed by GC it was confirmed that ketones were formed with a high conversion factor and a high yield in all cases. With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in hexane, Time= 20h, Reflux, Inert atmosphere, Solvent, Temperature Patent; Kanto Kagaku Kabushiki Kaisha; Yamaguchi, Ryohei; Fujita, Ken-ichi; (26 pag.); US2016/297844; (2016); (A1) English View in Reaxys With nickel dichloride in water, Time= 24h, T= 20 °C , pH= 9, Inert atmosphere, Irradiation Zhao, Lei-Min; Meng, Qing-Yuan; Fan, Xiang-Bing; Ye, Chen; Li, Xu-Bing; Chen, Bin; Ramamurthy, Vaidhyanathan; Tung, Chen-Ho; Wu, Li-Zhu; Angewandte Chemie - International Edition; vol. 56; nb. 11; (2017); p. 3020 3024; Angew. Chem.; vol. 129; nb. 11; (2017); p. 3066 - 3070,5 View in Reaxys OH O

O O

Rx-ID: 33359683 View in Reaxys 3/449 Yield 21 %, 36 %, 5 %, 8 %

Conditions & References Catalytic hydrogenation of furfural was carried out in a 25 ml stainless steel autoclave equipped with a magnetic stirrer. Typically, a mixture of furfural (1mmol), catalyst (50mg) and water (10mL) were put into the reactor and purged with H2 for several times. The reactor was pressured with H2 to 2MPa. Then the autoclave was heated to the desired temperature for 4h. After reaction, the reactor was cooled to ambient temperature. The liquid products were extracted by ethyl acetate and then analyzed by a gas chromatograph (GC, Kexiao 1690) with a HP-INNOMAX capillary column (30m×0.25mm×0.25μm) and GC-MS (Agilent 7890A). The GC detecting conditions were as follows: nitrogen was the carrier gas; injection port temperature was 280 °C; detector (FID) temperature was 280°C. Column temperature heated from 40°C to 250 °C with a heating rate of 10°C/min. The n-hexanol was used as internal standard to quantify the products. With hydrogen in water, Time= 4h, T= 150 °C , p= 15001.5Torr , Autoclave, Reagent/catalyst Ma, Yan-Fu; Wang, Hao; Xu, Guang-Yue; Liu, Xiao-Hao; Zhang, Ying; Fu, Yao; Chinese Chemical Letters; vol. 28; nb. 6; (2017); p. 1153 - 1158

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View in Reaxys 7.63 %, 16.42 %, 12.12 %, 16.49 %

With hydrogen in water, Time= 0.5h, T= 175 °C , p= 60006Torr Hronec, Milan; Fulajtarova, Katarina; Catalysis Communications; vol. 24; (2012); p. 100 - 104 View in Reaxys

O O

Rx-ID: 33359684 View in Reaxys 4/449 Yield 68 %, 14 %

Conditions & References Catalytic hydrogenation of furfural was carried out in a 25 ml stainless steel autoclave equipped with a magnetic stirrer. Typically, a mixture of furfural (1mmol), catalyst (50mg) and water (10mL) were put into the reactor and purged with H2 for several times. The reactor was pressured with H2 to 2MPa. Then the autoclave was heated to the desired temperature for 4h. After reaction, the reactor was cooled to ambient temperature. The liquid products were extracted by ethyl acetate and then analyzed by a gas chromatograph (GC, Kexiao 1690) with a HP-INNOMAX capillary column (30m×0.25mm×0.25μm) and GC-MS (Agilent 7890A). The GC detecting conditions were as follows: nitrogen was the carrier gas; injection port temperature was 280 °C; detector (FID) temperature was 280°C. Column temperature heated from 40°C to 250 °C with a heating rate of 10°C/min. The n-hexanol was used as internal standard to quantify the products. With hydrogen in water, Time= 4h, T= 160 °C , p= 15001.5Torr , Autoclave, Reagent/catalyst Ma, Yan-Fu; Wang, Hao; Xu, Guang-Yue; Liu, Xiao-Hao; Zhang, Ying; Fu, Yao; Chinese Chemical Letters; vol. 28; nb. 6; (2017); p. 1153 - 1158 View in Reaxys

55.74 %, 7.91 %

With 5 platinum on carbon, hydrogen in water, Time= 2.5h, T= 160 °C , p= 60006Torr Hronec, Milan; Fulajtarova, Katarina; Catalysis Communications; vol. 24; (2012); p. 100 - 104 View in Reaxys With water, hydrogen, Time= 4h, T= 160 °C , p= 30003Torr , Autoclave, Overall yield = 65 percent Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys Reaction Steps: 2 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water / 4 h / 160 °C / 30003 Torr / |Autoclave With water, hydrogen, sodium carbonate Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys Reaction Steps: 2 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water; pentanal / 4 h / 160 °C / 30003 Torr / |Autoclave With pentanal, water, hydrogen, sodium carbonate Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys Reaction Steps: 2 1: water / 4 h / 160 °C / 750.08 Torr / |Inert atmosphere; |Autoclave 2: hydrogen; water / 160 °C / 30003 Torr / |Autoclave With water, hydrogen Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940

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View in Reaxys Reaction Steps: 3 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water / 8 h / 160 °C / |Inert atmosphere; |Autoclave 3: hydrogen; water / 160 °C / 30003 Torr / |Autoclave With water, hydrogen, sodium carbonate Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys With 30 Cu/Co3O4, hydrogen in water, Time= 6h, T= 149.84 °C , p= 30003Torr , Autoclave, Reagent/catalyst, chemoselective reaction Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao; Green Chemistry; vol. 17; nb. 2; (2015); p. 1038 - 1046 View in Reaxys With hydrogen, cobalt in water, Time= 1h, T= 169.84 °C , p= 15001.5Torr , Autoclave, Reagent/catalyst, chemoselective reaction Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao; Green Chemistry; vol. 17; nb. 2; (2015); p. 1038 - 1046 View in Reaxys O O O

Rx-ID: 33359685 View in Reaxys 5/449 Yield 98 %

Conditions & References With hydrogen in water, Time= 7h, T= 160 °C , p= 30003Torr , Automated synthesizer Zhang, Gao-Shuo; Zhu, Ming-Ming; Zhang, Qi; Liu, Yong-Mei; He, He-Yong; Cao, Yong; Green Chemistry; vol. 18; nb. 7; (2016); p. 2155 - 2164 View in Reaxys

96 %

With hydrogen in water, Time= 2.5h, T= 160 °C , p= 30003Torr , Autoclave, Reagent/catalyst, Temperature, Pressure Fang, Ruiqi; Liu, Hongli; Luque, Rafael; Li, Yingwei; Green Chemistry; vol. 17; nb. 8; (2015); p. 4183 - 4188 View in Reaxys

76.5 %

With 5 platinum on carbon, hydrogen in water, Time= 0.5h, T= 160 °C , p= 60006Torr , chemoselective reaction Hronec, Milan; Fulajtarova, Katarina; Catalysis Communications; vol. 24; (2012); p. 100 - 104 View in Reaxys With water, hydrogen, Time= 4h, T= 160 °C , p= 15001.5Torr , Autoclave, Reagent/catalyst Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys With hydrogen, 18O-labeled water, Time= 4h, T= 160 °C Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys Reaction Steps: 2 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: 5-hydroxymethyl-2-furfuraldehyde; hydrogen; water / 4 h / 160 °C / 30003 Torr / |Autoclave With 5-hydroxymethyl-2-furfuraldehyde, water, hydrogen, sodium carbonate

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Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys With hydrogen in water, Time= 6h, T= 150 °C , p= 10501.1 - 30003Torr , Reagent/catalyst Bui, Tuong V.; Sooknoi, Tawan; Resasco, Daniel E.; ChemSusChem; vol. 10; nb. 7; (2017); p. 1631 - 1639 View in Reaxys O O

O OH

Rx-ID: 40786159 View in Reaxys 6/449 Yield 73 %

Conditions & References With hydrogen in water, Time= 2.5h, T= 160 °C , p= 30003Torr , Autoclave, Reagent/catalyst Fang, Ruiqi; Liu, Hongli; Luque, Rafael; Li, Yingwei; Green Chemistry; vol. 17; nb. 8; (2015); p. 4183 - 4188 View in Reaxys

14 %, 56 %

Catalytic hydrogenation of furfural was carried out in a 25 ml stainless steel autoclave equipped with a magnetic stirrer. Typically, a mixture of furfural (1mmol), catalyst (50mg) and water (10mL) were put into the reactor and purged with H2 for several times. The reactor was pressured with H2 to 2MPa. Then the autoclave was heated to the desired temperature for 4h. After reaction, the reactor was cooled to ambient temperature. The liquid products were extracted by ethyl acetate and then analyzed by a gas chromatograph (GC, Kexiao 1690) with a HP-INNOMAX capillary column (30m×0.25mm×0.25μm) and GC-MS (Agilent 7890A). The GC detecting conditions were as follows: nitrogen was the carrier gas; injection port temperature was 280 °C; detector (FID) temperature was 280°C. Column temperature heated from 40°C to 250 °C with a heating rate of 10°C/min. The n-hexanol was used as internal standard to quantify the products. With hydrogen in water, Time= 1h, T= 160 °C , p= 15001.5Torr , Autoclave Ma, Yan-Fu; Wang, Hao; Xu, Guang-Yue; Liu, Xiao-Hao; Zhang, Ying; Fu, Yao; Chinese Chemical Letters; vol. 28; nb. 6; (2017); p. 1153 - 1158 View in Reaxys

29 %

With Ru/C, hydrogen in water, Time= 2.5h, T= 160 °C , p= 30003Torr , Autoclave, Reagent/catalyst Fang, Ruiqi; Liu, Hongli; Luque, Rafael; Li, Yingwei; Green Chemistry; vol. 17; nb. 8; (2015); p. 4183 - 4188 View in Reaxys 2 :An irrigation packed bed reactor made of SUS 316 having an outer diameter of 10 mmφ, an inner diameter of 8 mmφ, and a length of 400 mm Was charged with 0.5 g of the catalyst obtained above and the upper and lower sides of the catalyst were fixed with quartz wool. On the reactor , A 1 wtpercent furfural aqueous solution was fed at a rate of 0.20 g / min and hydrogen was supplied at a rate of 50 m L / min. At that time, the catalyst part temperature of the reactor was 160 ° C., the reaction pressure was 0. It was 9 MPa. Table 1 shows the furfural conversion rate and the yield of the main products at 1.5 hours after the start of the reaction. The conversion of furfural and the yield of each product are values calculated by the following formula is there The same as in Example 1 except that in Example 1, the catalyst charged in the reactor was changed to 1.0 g . With hydrogen, Time= 1.5h, T= 160 °C , p= 67506.8Torr Patent; Nippon Shokubai Co., Ltd.; Kirishiki, Ken; Maeda, Ryohei; (8 pag.); JP2016/108282; (2016); (A) Japanese View in Reaxys O

Rx-ID: 41437320 View in Reaxys 7/449

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Yield

Conditions & References

75.3 %Chromat., 11.6 %Chromat., 13.1 %Chromat.

2.5. Catalytic test. General procedure: In a typical experiment, the catalyst (0.25 mmol) was mixed with cyclohexanol (50 mmol) in a 100 mL three-necked flask equipped with a reflux condenser, a magnetic stirrer and a thermometer. When the required temperature reached, 30percent aqueous hydrogen peroxide (75 mmol) was then added dropwise to the reaction mixture, with vigorous stirring for 300 min. Hydroxylamine sulfate (25 mmol) was added to the flask with vigorous stirring for a certain time. After the completionof reaction, the reaction mixture was divided into two phases. Water phase was extracted with dichloromethane and the product swere identified by a Thermo Trace DSQ gas chromatograph–mass spectrometer. The products were analyzed by a SP-3420A gas chromatograph equipped with a KB-Wax column (30 m, 0.32 mm id, 0.25 μm film thickness) with toluene as internal standard. Stage 1: With C19H42N(1+)*2H(1+)*O40PW12 (3-), water, dihydrogen peroxide, Time= 6h, T= 80 °C Stage 2: With hydroxyammonium sulfate, Time= 5h, T= 100 °C , Beckmann Rearrangement, Catalytic behavior, Overall yield = 82.8 percentChromat.; chemoselective reaction Wang, Hefang; Hu, Rongbin; Yang, Yongfang; Gao, Meidan; Wang, Yanji; Catalysis Communications; vol. 70; (2015); p. 6 - 11 View in Reaxys 2.2. Catalytic testing General procedure: In a typical procedure, Na2WO4 (2.75 mmol) and an ionicliquid were mixed with cyclohexanol (50 mmol) in a 100‐mLthree‐necked flask equipped with a reflux condenser, magneticstirrer and a thermometer. The resulting mixture was thenheated to the required temperature, and treated with 30percentH2O2 (75 mmol), which was added in a dropwise manner to thereaction mixture with vigorous stirring over 5 h. Hydroxylaminesulfate (25 mmol) was then added to the flask with vigorousstirring over a certain period of time. Upon completion ofthe reaction, the mixture was allowed to settle to give twophases. The aqueous phase was collected and extracted withdichloromethane, and the extracted products were identifiedby gas chromatography‐mass spectrometry using a ThermoTrace DSQ gas chromatograph‐mass spectrometer (ThermoElectron, Massachusetts, America). The products were analyzedon an SP‐3420A gas chromatograph equipped with a KB‐Waxcolumn (30 m × 0.32 mm × 0.25 μm). Stage 1: With [TMBSA][HSO4], 6Na(1+)*O4W(2-)*2H2O, dihydrogen peroxide, T= 80 °C , Green chemistry Stage 2: With hydroxyammonium sulfate, Time= 5h, T= 80 °C , Green chemistry Wang, Hefang; Jia, Liyuan; Hu, Rongbin; Gao, Meidan; Wang, Yanji; Chinese Journal of Catalysis; vol. 38; nb. 1; (2017); p. 58 - 64 View in Reaxys

O HO

Rx-ID: 44768841 View in Reaxys 8/449 Yield

Conditions & References For the purposes of promoting an understanding of the principles of the present disclosure, reference will now be made to the embodiments illustrated in the drawings, and specific language will be used to describe the same. It will nevertheless be understood that no limitation of the scope of this disclosure is thereby intended. (0013) Hydrodeoxygenation (HDO) is a promising strategy to overcome problems associated with biomass to biofuel conversion. Since bio-oil is a complex mixture, of generally more than 400 chemical species, a model compound is typically used to obtain insight into the HDO process. Guaiacol is one such representative compound owing to its two common oxygenated groups: hydroxyl and methoxyl. Extensive research has been conducted in this field. It should therefore be appreciated that while guaiacol is the model compound used to demonstrate the methods disclosed herein, such use is not intended to be limiting and rather, other biomass compounds can be used. In general, Group VIII metals (Pt, Pd, Ni, Rh, Ru, and so on) are used to activate guaiacol and to facilitate hydrogen donation, while Al2O3, ZrO2, SiO2 and activated carbon are considered to be effective supports. (0014) Although the use of hydrogen for deoxygenation of guaiacol is advantageous because it generates clean products (mainly water), it often carries high economic penalties arising from its production and transportation. In this context, methane, as the main component in natural gas (CH4>95percent) and major component of shale gas (typically CH4>70percent), is attractive as an alternative to H2 since it can serve as a hydrogen donor by releasing hydrogen at high temperature on noble metal surfaces, which makes it a potential promising reductant. (0015) To facilitate understanding of the methods disclosed herein, with Pt/C as catalyst, a guaiacol deoxygenation process using H2 is presented herein. Based on kinetics and catalyst characterization, deactivation mechanism and reaction pathways are also proposed. To overcome the high cost of

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H2, methane is used in the present disclosure to deoxygenate guaiacol. (0016) Results and Discussion: (0017) In preliminary work with Pt/C catalyst, the use of CH4 was shown to be successful for guaiacol deoxygenation, but significant catalyst deactivation was observed. This observation is similar to other works for CH4 reactions and is related to coking/carbon deposition. The deactivation issue has been addressed for other reactions by use of bimetallic catalysts, containing a primary metal and a promoter. Thus, in the present disclosure, a guaiacol deoxygenation process using methane is developed via Pt—Bi catalyst. (0018) Four cases (PtH2, PtCH4, PtBiH2 and PtBiCH4), derived from two catalysts (Pt/C, Pt—Bi/C) using either H2 or CH4 as reductant, were tested for deoxygenation of guaiacol under standard operating conditions: 300° C., 1 atm, 0.50 g catalyst, total gas (reductant gas, H2 or CH4:N2=1:1) flow rate 100 mL/min, and guaiacol feed rate 0.025 mL/min (liquid, at room temperature), corresponding to contact time 0.3 g catalyst·hr/g guaiacol. A Van Krevelen diagram (FIG. 1a) is used to evaluate the deoxygenation levels by analyzing O/C and H/C molar ratios in the liquid products, which compares hydrogenation vs. deoxygenation performance. Owing to catalyst deactivation, data taken at 60 min time on stream (TOS) is reported in FIG. 1a. It shows that guaiacol has H/C of 1.14 and O/C of 0.28, implying a high O content. The H/C ratios increase to 1.18-1.20 and O/C ratios decrease to 0.21-0.22 for all the four cases after deoxygenation, indicating that both hydrogenation and deoxygenation occur. It clearly shows that all four cases behave similarly in the early stages of TOS, although the initial conversions of guaiacol vary from 79percent-90percent (FIG. 1b). The high yield and good stability of PtH2 case have been reported. Since CH4 decomposes on Pt surface donating hydrogen, the PtCH4 case has a high initial guaiacol conversion. In fact, H2 is detected in the gaseous products. As shown in FIG. 1b, with increasing TOS, however, the PtCH4 case exhibits sharp deactivation, while the other three cases maintain good stability. As noted above, a possible reason for rapid deactivation in the PtCH4 case is carbon deposit and/or coking, resulting from CH4 decomposition. (0019) In the PtBiH2 case of FIG. 1b, good stability is obtained although the conversion is decreased by 10percent, as compared to the PtH2 case. Remarkably, PtBiCH4 also shows good catalyst stability, although the conversion is decreased further. For a C8 hydrocarbon reforming process using catalyst containing a Group VIII metal and low amounts of bismuth, a patent disclosed that addition of bismuth extended catalyst lifetime. In fact, this is the only prior work demonstrating catalyst stability using Bi as a promotor for gas-phase reactions at high temperature (>300° C.). Although the mechanism is unclear, our experiments also show that Bi promotor extends catalyst lifetime. It should also be noted that in a patent application, Fernando et al. describe the use of methane with an oxygenate to dehydrate and produce deoxygenated hydrocarbons, but no bimetallic catalysts or data for catalyst stability were reported. (0020) FIGS. 2a-2d show distribution of major components in both gaseous and liquid products at 60 min TOS under standard conditions (FIG. 2a corresponds to PtH2, FIG. 2b corresponds to PtCH4, FIG. 2c corresponds to PtBiH2, and FIG. 2d corresponds to PtBiCH4). Note that components less than 2 wt percent are neglected and all compositions are normalized with respect to the remaining components. Only three main products (phenol, catechol and cyclopentanone, total content >95 wt percent for all four cases) in the liquid are shown. For liquid products, all four cases have similar distributions and compositions. For gaseous products, the PtH2 and PtBiH2 cases generated CO and CH4, while PtCH4 and PtBiCH4 produced CO and C2H6 instead. Since our work using Pt and H2 suggested that CO and CH4 are generated along with cyclopentanone, we can conclude that C2H6 is generated by the use of CH4. Thus, a conceptual scheme is presented for comparison of H2 and CH4 deoxygenation processes. <in-line-formulae>For hydrogen deoxygenation: R2O+2H2→2RH+H2O</in-line-formulae> <in-line-formulae>For methane deoxygenation: R2O+4CH4→2RH+2C2H6+H2O</in-line-formulae> (0021) It is disclosed that CH4 decomposes on Pt surface and contributes one H atom for guaiacol deoxygenation and water formation, similar to the H2 process, while the residual methyl combines with another methyl to form ethane. This assumption is supported by the low reaction barrier of CH4 decomposition at elevated temperature, along with detected H2 and C2H6 molecules in our experiments. (0022) To further understand Pt—Bi performance for guaiacol deoxygenation using CH4 as reductant, different temperatures (300-450° C.) were investigated for guaiacol conversion and carbon recovery in liquid and gaseous products, as shown in FIGS. 3a-3b. FIG. 3a shows increase of guaiacol conversion with temperature, where conversions >90percent are reached for 400-450° C. Remarkably, as shown in FIGS. 1a and 1b, such conversion is obtained at 300° C. when Pt and H2 are used. Therefore, reaction rate is decreased by either using CH4 as reductant or Pt—Bi as catalyst. Besides guaiacol conversion, carbon recovery in the liquid phase is another important factor to assess the catalyst performance, as shown in FIG. 3b. Two major factors are considered to affect carbon recovery in the liquid phase: guaiacol conversion (to the three main liquid products) and other reactions that decompose guaiacol to produce gaseous products, which occur on carbon-supported noble metal catalysts. Along with temperature increase, carbon recovery in liquid product first increased and then decreased after 400° C., while carbon recovery in gaseous products shows the opposite trend. From the present work, 400° C. can be considered as the optimal temperature accounting for trade-off between guaiacol conversion and carbon recovery in liquid products. (0023) The kinetic behavior of Pt—Bi catalyst at 400° C. was studied by varying feed rates of guaiacol and CH4 under otherwise standard conditions. The data for each contact time, taken at 60 min TOS, is shown in FIG. 4. It illustrates that phenol, as the main product, rises with contact time increase, while the other two products remain essentially unchanged. As compared to the PtH2 case (FIGS. 1a and 1b; 300° C., 0.3 g catalyst·hr/g guaiacol), the results of FIGS. 3a, 3b and 4 demonstrate that equivalent guaiacol conversion can be achieved for the case of Pt—Bi catalyst with

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methane by compensating with either higher temperature or longer contact time (>0.5 g catalyst·hr/g guaiacol). (0024) In the present work, CH4 is used as novel reductant to deoxygenate guaiacol, a model compound of pyrolysis bio-oils. With the Pt/C catalyst, CH4 exhibits as good deoxygenation performance as H2 with respect to guaiacol conversion and product distribution. The lifetime of Pt/C catalyst, however, was low (<3 hrs). With addition of bismuth as promoter, the lifetime of Pt—Bi/C is extended (no significant deactivation in 5 hrs), although catalyst performance decreases somewhat, which could be compensated by either higher reaction temperature or longer contact time. The current work provides a new approach for bio-oil upgrading using methane as reductant instead of hydrogen. (0025) Those skilled in the art will recognize that numerous modifications can be made to the specific implementations described above. The implementations should not be limited to the particular limitations described. Other implementations may be possible. With methane, platinum on carbon, T= 300 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Temperature Patent; PURDUE RESEARCH FOUNDATION; Varma, Arvind; Xiao, Yang; (10 pag.); US2017/29712; (2017); (A1) English View in Reaxys

F F

H N

F F

Rx-ID: 44821957 View in Reaxys 9/449 Yield

Conditions & References in aq. phosphate buffer, [D3]acetonitrile, water-d2, T= 20 °C , pH= 5, Kinetics Liu, Bin; Thayumanavan; Journal of the American Chemical Society; vol. 139; nb. 6; (2017); p. 2306 - 2317 View in Reaxys

N+

O– O

Cl OO

Rx-ID: 45089515 View in Reaxys 10/449 Yield

Conditions & References With deutero-chloric acid, water-d2, Reagent/catalyst Gong, Wanjun; Ma, Jun; Zhao, Zhiyong; Gao, Fang; Liang, Feng; Zhang, Haijun; Liu, Simin; Journal of Organic Chemistry; vol. 82; nb. 6; (2017); p. 3298 - 3301 View in Reaxys

Rx-ID: 45753755 View in Reaxys 11/449 Yield

Conditions & References With calcium hypochlorite, acetic acid in water, acetonitrile, Time= 1.5h, T= 20 °C , regioselective reaction Gilissen, Pieter J.; Blanco-Ania, Daniel; Rutjes, Floris P. J. T.; Journal of Organic Chemistry; vol. 82; nb. 13; (2017); p. 6671 - 6679 View in Reaxys

Rx-ID: 45988666 View in Reaxys 12/449

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Yield

Conditions & References

48 %, 11 %, 7 %, 7 %, 10 %

2 :2 g of furfural,10g water,36 g of methanol and 0.5 g of catalyst into a 100 mL autoclave,To the reactor charge and discharge N2 three times,To purge the air in the reactor,And then continue to fill N2 to make the initial pressure within the kettle to 1MPa.The autoclave was heated to 260 ° C at a heating rate of 3 ° C / min,And stay at this temperature for 4h,After the reaction, the reaction vessel was transferred to cold water and cooled to room temperature (cooling rate of about 10 ° C / min)The gas and liquid products in the autoclave were quantitatively analyzed when the temperature of the reactor was stable.The results showed that the conversion rate of furfural was 95percent under the catalyst and reaction conditions,Furan yield reached 52percentMethyl furan yield of 29percentThe yield of cyclopentanone was 4percentButanol yield of 7percentThe yield of tetrahydrofuran was 1percentThe other components were yielded at 2percent. With nickel supported catalyst in methanol, water, Time= 4h, T= 260 °C , p= 7500.75Torr , Inert atmosphere, Autoclave, Reagent/catalyst Patent; Chinese Academy Of Sciences Process Engineering Institute; Wang Ze; Fu Chaolin; Song Wenli; Lin Weigang; Li Songgeng; (9 pag.); CN106496165; (2017); (A) Chinese View in Reaxys

O OH

OH OH

Rx-ID: 46139213 View in Reaxys 13/449 Yield

Conditions & References Hydrogenation of furfural (99percent, Sigma—Aldrich) in aqueous solution (3.5 wt.percent, 100 mL) in the presence of PdRu/CNTs (300 mg) was carried out in a periodic mode in a Limbo Liautoclave (Büchi AG) at a temperature of 473 K and overallpressure of 8 MPa with continuous stirring of the reaction mixture (1500 min–1). The duration of any experiment was 3 h. With hydrogen in water, Time= 3h, T= 199.84 °C , p= 60006Torr , Autoclave, Reagent/catalyst Mironenko; Belskaya; Lavrenov; Likholobov; Russian Chemical Bulletin; vol. 66; nb. 4; (2017); p. 673 - 676; Izv. Akad. Nauk, Ser. Khim.; nb. 4; (2017); p. 673 - 676,4 View in Reaxys O

Rx-ID: 276442 View in Reaxys 14/449 Yield 48 %

Conditions & References With dihydrogen peroxide, vanadium phosphorus oxide in acetonitrile, Time= 20h, T= 50 °C Pillai, Unnikrishnan R.; Sahle-Demessie, Endalkachew; New Journal of Chemistry; vol. 27; nb. 3; (2003); p. 525 528 View in Reaxys

12.15 %

Stage 1: With 3C46H56N2O4 (4-)*7Cu(2+)*2HO(1-)*2C3H7NO*2H2O in acetonitrile, T= 55 °C Stage 2: With dihydrogen peroxide in water, acetonitrile, Time= 6h, T= 55 °C Fang, Yu; Gong, Wei; Liu, Lujia; Liu, Yan; Cui, Yong; Inorganic Chemistry; vol. 55; nb. 20; (2016); p. 10102 10105 View in Reaxys With ethyl bromide, hydrogen bromide, oxygen, T= 185 °C Patent; Shell Devel. Co.; US2391740; (1944) View in Reaxys in pyridine, GoAggIII (acetic acid, FeCl3*6 H2O, Zn, picolinic acid), other Gif systems, relative reactivity with cyclohexane, Kinetics, Mechanism

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Barton, Derek H. R.; Doller, Dario; Geletii, Yurii V.; Tetrahedron Letters; vol. 32; nb. 31; (1991); p. 3811 - 3814 View in Reaxys 46 % Chromat.

With cis-lt;RuVI(6,6'-Cl2bpy)2O2gt;lt;ClO4gt; in acetonitrile, Time= 0.5h, T= 20 °C , Oxidation Che; Cheng; Chan; Lau; Mak; Journal of Organic Chemistry; vol. 65; nb. 23; (2000); p. 7996 - 8000 View in Reaxys With oxygen, T= 19.84 °C , Neat (no solvent), UV-irradiation Tada, Mizuki; Akatsuka, Yusaku; Yang, Yong; Sasaki, Takehiko; Kinoshita, Mutsuo; Motokura, Ken; Iwasawa, Yasuhiro; Angewandte Chemie - International Edition; vol. 47; nb. 48; (2008); p. 9252 - 9255 View in Reaxys With iron(III) chloride, thymidyl acetic acid, dihydrogen peroxide in water, acetonitrile, Time= 10h, T= 60 °C Al-Hunaiti, Afnan; Räisänen, Minnä; Repo, Timo; Chemical Communications; vol. 52; nb. 10; (2016); p. 2043 2046 View in Reaxys O

Rx-ID: 747217 View in Reaxys 15/449 Yield 100 %

Conditions & References With oxygen, palladium(II) sulfate, PdSO4-H3PMo6W6O40 in cyclohexane, water, Time= 6h, T= 30 °C Ogawa, Haruo; Fujinami, Hideharu; Taya, Kazuo; Teratani, Shousuke; Journal of the Chemical Society, Chemical Communications; nb. 24; (1981); p. 1274 - 1275 View in Reaxys

100 %

With oxygen, H3PMo6W6O40 in cyclohexane, water, Time= 6h, T= 29.9 °C , p= 760Torr Ogawa; Fujinami; Taya; Teratani; Bulletin of the Chemical Society of Japan; vol. 57; nb. 7; (1984); p. 1908 - 1913 View in Reaxys

100 %

With palladium(II) sulfate, oxygen, H3PMo6W6O40 in cyclohexane, water, Time= 6h, T= 29.9 °C , p= 760Torr , other time, other Pd(II) salt, other concentration of catalyst, Product distribution, Rate constant Ogawa; Fujinami; Taya; Teratani; Bulletin of the Chemical Society of Japan; vol. 57; nb. 7; (1984); p. 1908 - 1913 View in Reaxys

80.2 %

With oxygen, palladium diacetate, scandium tris(trifluoromethanesulfonate) in water, acetonitrile, Time= 24h, T= 80 °C , p= 15201Torr , Autoclave, Wacker Oxidation, Reagent/catalyst Qin, Shuhao; Dong, Lei; Chen, Zhuqi; Zhang, Sicheng; Yin, Guochuan; Dalton Transactions; vol. 44; nb. 40; (2015); p. 17508 - 17515 View in Reaxys

72.2 %

5 :To the autoclave made from 40-mL stainless steel, dichlorobis (benzonitrile) palladium 38.4 mg (0.10mmol), After preparing 5.0 mL of methanol, and 0.5 mL of water as 272.5 mg (4.0mmol) and a solvent and sealing cyclopentene, oxygen gas was introduced and 0.5MPa (G) was pressurized. After having heated the whole picture, stirring at 60 degrees C for 5 hours and oxidizing cyclopentene, the whole picture was cooled, and at 0 degree C, it agitated for 1 hour, it ranked next, and returned the pressure in autoclave to ordinary pressure.THF was added to reaction mixture and dilution liquid was obtained. Gas chromatographic assay was conducted about the filtrate obtained by carrying out filtration removal of the solid in this dilution liquid using a 0.5-micrometer filter.As a result, the yield of cyclopentanone was 66.3percent to raw material cyclopentene. The survival rate of cyclopentene was 0percent. In the working example 1, the solvent was changed into 1-butanol and oxidation reaction of cyclopentene, filtration treatment of reaction mixture, and analysis of filtrate were conducted like the working example 1 except not having added water further.As a result, the yield of cyclopentanone was 72.2percent to raw material cyclopentene. The survival rate of cyclopentene was 0percent. With bis(benzonitrile)palladium(II) dichloride, oxygen in water, tert-butyl alcohol, Time= 5h, T= 60 °C , p= 3750.38Torr , Autoclave, Reagent/catalyst, Solvent, Temperature, Pressure

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Patent; NipponZeonCo., Ltd.; University of Tokyo; Sugawara, Takashi; Nakano, Keita; Kobayashi, Shu; (12 pag.); JP2016/88903; (2016); (A) Japanese View in Reaxys 50 %

With oxygen, copper(I)ketenide, Time= 10h, T= 20 °C , p= 1360Torr 'Femi-Onadeko, Bankole; Acta Chimica Hungarica; vol. 122; nb. 2; (1986); p. 175 - 180 View in Reaxys

44 %

With N,N,N,N,N,N-hexamethylphosphoric triamide, dichloro bis(acetonitrile) palladium(II), oxygen, copper(l) chloride in 1,2-dichloro-ethane, Time= 19h, T= 50 °C Hosokawa; Aoki; Takano; Nakahira; Yoshida; Murahashi; Journal of the Chemical Society - Series Chemical Communications; nb. 21; (1991); p. 1559 - 1560 View in Reaxys With 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

75 % Chromat.

With palladium diacetate, p-benozquinone in water, acetonitrile, Ambient temperature, electrolysis was used for the oxidation Tsuji, Jiro; Minato, Makoto; Tetrahedron Letters; vol. 28; nb. 32; (1987); p. 3683 - 3686 View in Reaxys With lithium borohydride, sodium dichromate, sulfuric acid, boron trifluoride diethyl etherate, 1.) ethyl ether, 25-30 deg C, 2 h; 2.) water, ethyl ether, reflux, 2 h, Yield given. Multistep reaction Brown, Herbert C.; Garg, Chandra P.; Tetrahedron; vol. 42; nb. 20; (1986); p. 5511 - 5514 View in Reaxys With oxygen, PdCl2(DEAc)2( in ethanol, Time= 8h, T= 30 °C , p= 860Torr , oxidation with other palladium-complex, Product distribution Takehira, Katsuomi; Hayakawa, Takashi; Orita, Hideo; Chemistry Letters; (1985); p. 1835 - 1838 View in Reaxys

99 % Chromat.

With dihydrogen peroxide, tetraphenylphosphonium, sodium hydrogencarbonate, WO(O2)(QO)4 in acetonitrile, Time= 0.25h, T= 25 °C Maiti, Swarup K.; Dinda, Subhajit; Gharah, Narottam; Bhattacharyya, Ramgopal; New Journal of Chemistry; vol. 30; nb. 3; (2006); p. 479 - 489 View in Reaxys With dinitrogen monoxide, Time= 20h, T= 200 °C , pressure Starokon; Dubkov; Babushkin; Parmon; Panov; Advanced Synthesis and Catalysis; vol. 346; nb. 2-3; (2004); p. 268 - 274 View in Reaxys Reaction Steps: 3 1: KMnO4 / H2O / -5 °C 2: pyridine / 2.5 h / 3 °C 3: acetic acid / rate constant: 171.4E5 With pyridine, potassium permanganate in water, acetic acid Wistuba, Eckehardt; Ruechardt, Christoph; Tetrahedron Letters; vol. 22; nb. 41; (1981); p. 4069 - 4072 View in Reaxys 1; 2; 3; 4; 5; 6; 7; 8 :33 cm3 of cyclopentene (Aldrich, 99percent) are poured into a 100 cm3 reactor made from stainless steel and provided with a stirrer (Parr Co.). The reactor is purged with nitrous oxide, and then the pressure of nitrous oxide is brought to 10 atm. The reactor is heated to 197° C. and maintained at this temperature during 5 hrs. On completion of the reaction, the reactor is cooled down to room temperature, the pressure is measured, and the final composition of the gaseous and liquid phases is analyzed by gas chromatography and chromatography-mass spectrometry techniques. From the obtained data the conversion of cyclopentene and the selectivity of the reaction

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for cyclopentanone are calculated; where CCyEN 0 is the initial cyclopentene concentration; CCyON is the cyclopentene concentration in reaction products; ΣCside is the total concentration of by-products. In the case of large conversions, the value X can be calculated also from the difference between the initial and final concentrations of cyclopentene: Example 2 is similar to Example 1, the difference being in that the reaction is carried out at 195° C. during 12 hours. Example 3 is similar to Example 2, the difference being in that the reaction is carried out at a temperature of 150° C. Example 4 is similar to Example 3, the difference being in that the reaction is carried out at 175° C. during 10 hours. Example 5 is similar to Example 4, the difference being in that the reaction is carried out at 225° C. during 3 hours. TABLE 1 Example T (° C.) Time (hrs) X (percent) S (percent) 1 197 5 7.7 98 2 195 12 15.6 97 3 150 12 3.5 97.5 4 175 10 8.5 98 5 225 3 13 99 Example 6 This Example is a comparative one. The experiment is carried out as in Example 1, the difference being in that the reactor is charged with 5 ml of cyclopentene. With such charging under the reaction conditions the whole of the cyclopentene is in the gaseous phase. As a result of the experiment, the conversion of cyclopentene was approximately 0.5percent. This result indicates that under the abovesaid conditions the reaction in the gas phase practically does not go. EXAMPLES 7-8 These Examples, as compared with Example 1, demonstrate the influence of the nitrous oxide concentration on the process characteristics (Table 2). The nitrous oxide concentration in the reaction mixture is preset by the value of its initial pressure at room temperature, PN 2 O 0. Example 7 is similar to Example 1, the difference being in that the initial pressure of nitrous oxide at room temperature in this experiment is set to be equal to 25 atm. Example 8 is similar to Example 1, the difference being in that the initial pressure of nitrous oxide in this experiment is set to be equal to 5 atm. TABLE 2 ExamplePN 2 O 0 (atm) T ° C.) X (percent) S (percent) 1 10 197 7.7 98 7 25 197 20.5 99 8 5 197 4.0 98 With dinitrogen monoxide, Time= 3 - 12h, T= 150 - 225 °C , p= 3800.26 - 19001.3Torr , Product distribution / selectivity Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 10 :Examples 9-10 (Table 3) demonstrate the possibility of carrying out the process in the presence of a catalyst. Example 9 is similar to Example 1, the difference being in that the reaction is carried out in the presence of 0.15 g of Fe2O3/SiO2 (2.8 wt. percent of Fe2O3). The catalyst is prepared by impregnating SiO2 with a solution of FeCl3, dried at 110° C. and calcined in air at 500° C. for 2 hrs. Example 10 is similar to Example 1, the difference being in that the reaction is carried out in the presence of 0.5 g of Ag/SiO2 (1 wt. percent of Ag). The catalyst is prepared by impregnating SiO2 with a solution of AgNO3, dried at 110° C. and calcined in air at 500° C. for 2 hrs. TABLE 3 Example Catalyst T (° C.) X (percent) S (percent) 9Fe2O3/SiO2 197 7.5 97.5 10Ag/SiO2 197 8 97 With dinitrogen monoxide, 1 wt silver/SiO2, Time= 5h, T= 197 °C , p= 7600.51Torr , Product distribution / selectivity Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 9 :Examples 9-10 (Table 3) demonstrate the possibility of carrying out the process in the presence of a catalyst. Example 9 is similar to Example 1, the difference being in that the reaction is carried out in the presence of 0.15 g of Fe2O3/SiO2 (2.8 wt. percent of Fe2O3). The catalyst is prepared by impregnating SiO2 with a solution of FeCl3, dried at 110° C. and calcined in air at 500° C. for 2 hrs. Example 10 is similar to Example 1, the difference being in that the reaction is carried out in the presence of 0.5 g of Ag/SiO2 (1 wt. percent of Ag). The catalyst is prepared by impregnating SiO2 with a solution of AgNO3, dried at 110° C. and calcined in air at 500° C. for 2 hrs. TABLE 3 Example Catalyst T (° C.) X (percent) S (percent) 9Fe2O3/SiO2 197 7.5 97.5 10Ag/SiO2 197 8 97 With dinitrogen monoxide, Time= 5h, T= 197 °C , p= 7600.51Torr , Product distribution / selectivity Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 14 :Example 14 is similar to Example 13, the difference being in that instead of acetonitrile use is made of heptane and the reaction is carried out at 220° C. for 5 hrs. With dinitrogen monoxide in n-heptane, Time= 5h, T= 220 °C , p= 7600.51Torr , Product distribution / selectivity

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Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 12 :Example 12 is similar to Example 1, the difference being in that 10 ml of cyclopentene and 50 ml of cyclohexane are poured into the reactor. With dinitrogen monoxide in cyclohexane, Time= 5h, T= 195 °C , p= 7600.51Torr , Product distribution / selectivity Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 13 :Example 13 is similar to Example 3, the difference being in that 10 ml of cyclopentene and 50 ml of acetonitrile are poured into the reactor. With dinitrogen monoxide in acetonitrile, Time= 5h, T= 150 °C , p= 7600.51Torr , Product distribution / selectivity Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 11 :These Examples demonstrate the possibility of cyclopentene oxidation in the presence of a solvent (Table 4). Example 11 is similar to Example 1, the difference being in that 10 ml of cyclopentene and 75 ml of isobutanol are poured into the reactor. With dinitrogen monoxide in 2-methyl-propan-1-ol, Time= 5h, T= 195 °C , p= 7600.51Torr , Product distribution / selectivity Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 19 :Example 19 is similar to Example 17, the difference being in that instead of nitrogen argon is used, in which the concentration of nitrous oxide is 40percent. The initial pressure of the mixture of N2O and Ar is set to be 43 atm. With dinitrogen monoxide, Time= 12h, T= 195 °C , p= 32682.2Torr , Mixed with argon, Product distribution / selectivity Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 20 :Example 20 is similar to Example 19, the difference being in that carbon dioxide gas is used instead of argon. With dinitrogen monoxide, Time= 12h, T= 195 °C , p= 32682.2Torr , Mixed with carbon dioxide, Product distribution / selectivity Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 15; 16; 17; 18 :Examples 15-20 (Table 5) demonstrate the possibility of carrying out the reaction with diluted mixtures of nitrous oxide. Example 15 is similar to Example 7, the difference being in that instead of pure nitrous oxide its mixture with an inert gas-nitrogen is fed to the reactor, in which mixture the concentration of N2O is 70percent The initial pressure of the mixture in the reactor (P0) is set to be 49 atm. Example 16 is similar to Example 15, the difference being in that the concentration of N2O in the mixture with nitrogen is 20percent. Example 17 is similar to Example 16, the difference being in that the initial pressure in the reactor is set to be 98 atm. The reaction is carried out at 195° C. for 12 hours. Example 18 is similar to Example 15, the difference being in that the concentration of nitrous oxide is 50percent, and the initial pressure of the mixture of N2O and N2 is set to be 32 atm. The reaction is carried out at 225° C. for 3 hours. With dinitrogen monoxide, Time= 3 - 12h, T= 195 - 225 °C , p= 24321.6 - 74485Torr , Mixed with nitrogen, Product distribution / selectivity

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Patent; Panov, Gennady Ivanovich; Dubkov, Konstantin Alexandrovich; Starokon, Evgeny Vladimirovich; Pirutko, Larisa Vladimirovna; US2006/106258; (2006); (A1) English View in Reaxys 1 With dinitrogen monoxide, T= 280 °C , p= 225023Torr Patent; BASF AKTIENGESELLSCHAFT; WO2006/32532; (2006); (A1) German View in Reaxys 1 :Example 1 was carried out in a reactor with downstream flash and distillation stage.The reactor consists of a series of 16 single tubes (outer diameter=10 mm, wall thickness=2 mm, inner diameter=6mm, length=5.3 m) that were spirally coiled (radius r=125 mm, pitch P=30 mm). The reaction volume inclusive the connecting parts is 2510 ml in total.The tube is equipped with a double jacket (outer tube: outer diameter=20 mm, wall thickness=2 mm, annular gap width=3 mm) through which a cooling liquid is pumped in direct flow to remove the reaction heat (Marlotherm SH of the firm Sasol). The temperature of the entering cooling agent is adjusted by means of an external thermostat at 280+/-2° C. Directly at the exit of the reactor is a pressure maintenance that keeps the pressure in the reactor constantly at 280 bar.The fresh cyclopentene is metered into the reactor with 172.5 g/h. Cyclopentene is obtained from the distillation of a C5-cut of a steam cracker and has the following composition (percent by weight): cyclopentene (ca. 93.2percent), cyclopentane (ca. 5.7percent), 2-methyl-2-butene (ca. 1.1percent), 2,2-dimethylbutane (ca. 0.17percent).By mixing of this stream with a cyclopentene feedback stream a stream of the following composition is generated: cyclopentene (ca. 48.8percent), cyclopentane (ca. 46.2percent), 2-methyl-2-butane (ca. 3.1percent), acetone (ca. 2.0percent), 2,2-dimethylbutane (ca. 0.96percent). This stream is then metered to the reactor by means of a metering pump (rate of flow: 1632 g/h).As further stream liquid N2O (content of N2O>99.5percent by volume, firm Messer Griesheim) is metered to the reactor with ca. 99.2 g/h. The molar ratio of cyclopentene to N2O in the reactor feed is 0.192 mol/mol.The cyclopentene conversion in a straight passage is 19.6percent and the N2O conversion is ca. 99.6percent. After pressure maintenance the reaction discharge is expanded in two stages with two flash vessels being operated at 11 bara and 1.1 bara to a pressure of 1.1 bara and cooled down. The gaseous components are separated and in a secondary cooler (operated at +5° C.) the hydrocarbons contained therein are condensed out as completely as possible. The gas phase (ca. 64.5 g/h) has the following composition: N2 (96.4percent by volume), N2O (0.41percent by volume), ethylene (0.28percent by volume), cyclopentene (0.37percent by volume), cyclopentane (0.33percent by volume), further C5-components (545 vppm).The obtained liquid phase is separated in a distillation column (bubble cap column with 5 column units 106 cm*50 mm, each 10 plates). 187.7 g/h of a stream having the following composition (percent by weight) are obtained as bottom product: cyclopentanone (ca. 96.8percent), cyclopentane (ca. 1.3percent), 4-pentenal (ca. 1.3percent), isopropylmethylketone (ca. 0.8percent), cyclopentenoxid (ca. 0.5percent), cyclopentene-dimers (ca. 0.5percent), cyclopentene (ca. 0.03percent).Of the top product containing 43.4percent cyclopentene but no cyclopentanone about 14.9 g/h are discarded in order to avoid the increase of bycomponents, in particular of acetone and 2-methyl-2-butene. The residual (ca. 1460 g/h) is feeded back as cyclopentene-feedback stream to the mixing tap together with fresh-C5.According to this operation mode the space-time yield is ca. 72.4 g cyclopentanone/liter/reaction volume/hour. Per kg of cyclopentanone produced ca. 8.2 kg cyclopentene/ cyclopentane mixture have to be separated off and for the most part are feeded back. The required energy for the distillation is 0.73 kWh/kg cyclopentanone. With dinitrogen monoxide, T= 280 °C , p= 825.083 - 8250.83Torr , Gas phase, Product distribution / selectivity Patent; BASF SE Patents, Trademarks and Licences; US2010/179352; (2010); (A1) English View in Reaxys 1 :Example 1 The pilot plant according to FIG. 1 is used.Through stream 2, the fresh cyclopentene feed is metered in at 116.4 g/h. This originates from the distillation of a C5 cut of a steamcracker and has the following composition (percent by weight): cyclopentene (approx. 95.1percent), cyclopentane (approx. 3.4percent), 2-methyl-2-butene (approx. 1.2percent).This stream 2 is first mixed with stream 3 (return cyclopentene) in order to obtain a stream which has the following composition: cyclopentene (approx. 46.3percent), cyclopentane (approx. 51.9percent), 2-methyl-2butene (approx. 0.9percent), 2,2-dimethylbutane (approx. 0.81percent).This stream is then metered into the reactor with a metering pump (flow rate: approx. 2076 g/h). Through stream 1, liquid dinitrogen monoxide (dinitrogen monoxide content >99.8percent by volume, from Messer Griesheim) is metered into the reactor at approx. 74 g/h. The molar cyclopentene:dinitrogen monoxide ratio in the reactor feed is 0.11 mol/mol. The reactor consists of a tube (external diameter=60.3 mm, wall thickness=2.4 mm, length=3500 mm) filled with thin-wall stainless steel Raschig rings (6.x.6.x.0.3 mm). To determine the longitudinal temperature profile, a thermowell of external diameter 16 mm was installed along the reactor axis and provided with a 15-point thermocouple. The reaction volume is (minus random packings and thermowell), including connecting pieces, approx. 7 l in total. The pressure in the reactor is adjusted to

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100 bar with a suitable pressure-retaining device at the reactor outlet.The tube is provided with an insulating jacket composed of a nanoporous inorganic foam from Microtherm (two layers of thickness in each case 50 mm). In order to reduce the heat losses even further, a three-part trace-heating system is also installed on the outside of the insulating jacket, and is adjusted to (v.u.) 256, 275 317° C. (preliminary tests without addition of dinitrogen monoxide ensured that the heat losses are only very low. When the reactor inlet temperature is approx. 260° C., the remaining heat losses lead to a cooling by merely 3° C. up to the reactor outlet). The residence time distribution of the reactor was determined in a preliminary test with a radioactive marker. The Bodenstein number determined has the value of 117, which corresponds to an equivalent stirred tank cascade with 58 stirred tanks.The feed stream is fed into the reactor from the bottom via a heated inlet nozzle, in which the feed stream is also heated. At a reactor inlet temperature of 239.5° C. (measured at the lowermost thermocouple in the thermowell), the cyclopentene conversion in straight pass is 11percent and the dinitrogen monoxide conversion approx. 96percent. The selectivity for cyclopentanone based on cyclopentene is 96.8percent. The reactor output has a temperature of 295° C. The adiabatic temperature increase is thus 55.5° C. The reactor output is decompressed to 1 bar in a two-stage decompression and cooled. The gaseous components are removed and, in an aftercooler (which is operated at +5° C.), the hydrocarbons present therein are very substantially condensed out.The liquid phase, which of the liquid reactor output and of the condensate, is separated in a distillation column (bubble-cap tray column with 20 trays and liquid side draw). The bottom product obtained is 138.7 g/h of a stream with the following composition (percent by weight): cyclopentanone (approx. 95.3percent), cyclopentane (approx. 0.8percent), 4-pentenal (approx. 1.3percent), cyclopentene oxide (approx. 0.37percent), cyclopentene dimers (approx. 0.53percent), cyclopentene (approx. 0.08percent). The side draw product which comprises 45.6percent cyclopentene is recycled as stream 3 to the reactor.The combined gas phases (from decompression & top of the recycle column, approx. 47.7 l/h) have the following composition: N&2 (81.1percent

by volume), dinitrogen mon-

oxide (2.46percent by volume), cyclopentene (0.96percent by volume), cyclopentane (0.48percent by volume). With dinitrogen monoxide, T= 239.5 °C , Industry scale, Product distribution / selectivity Patent; BASF SE; US2011/152576; (2011); (A1) English View in Reaxys Catalytic reaction: In a typical procedure, 15 mL cyclopentene (0.17 mol), 60 mL ethyl alcohol (1.03 mol) and Pd–Cu (5:1)/γ-Al2O3 catalyst (0.24 g, 2.0 wtpercent of cyclopentene) were added into 0.1 L closed autoclave. The mixture was stirred (400 rpm/min) under 1.0 MPa oxygen pressure at 100 °C for 7 h. Specific parameters are provided in Supporting information. With Pd-Cu(5:1)/γ-Al2O3, oxygen in ethanol, Time= 7h, T= 100 °C , p= 7500.75Torr , Autoclave, Catalytic behavior, Reagent/catalyst, Solvent, Temperature, Pressure, chemoselective reaction Liu, Wei-Wei; Feng, Yi-Si; Wang, Guang-Yu; Jiang, Wei-Wei; Xu, Hua-Jian; Chinese Chemical Letters; vol. 27; nb. 6; (2016); p. 905 - 909 View in Reaxys O

Rx-ID: 1792690 View in Reaxys 16/449 Yield 100 %

Conditions & References With p-mentha-1,8-diene, palladium on activated charcoal, Time= 0.5h, Heating Holleben, Maria Luiza A. von; Zucolotto, Monica; Zini, Claudia A.; Oliveira, Eduardo R.; Tetrahedron; vol. 50; nb. 4; (1994); p. 973 - 978 View in Reaxys

100 %

With hydrogen, SC-1 Ni2B in methanol, Time= 24h, T= 25 °C , p= 760Torr Belisle, Christopher M.; Young, Yvette M.; Singaram, Bakthan; Tetrahedron Letters; vol. 35; nb. 31; (1994); p. 5594 - 5598 View in Reaxys

99 %

With diphenylsilane, zinc(II) chloride, tetrakis(triphenylphosphine) palladium(0) in chloroform, Time= 0.5h, Ambient temperature Keinan, Ehud; Greenspoon, Noam; Journal of the American Chemical Society; vol. 108; nb. 23; (1986); p. 7314 7325 View in Reaxys

80 %

With diisobutyl-aluminum-ethylate in diethyl ether, Time= 24h, T= 25 °C

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Cha, Jin Soon; Kwon, Oh Oun; Kwon, Sang Yong; Organic Preparations and Procedures International; vol. 28; nb. 3; (1996); p. 355 - 360 View in Reaxys 74%

7 : Olefination of Cyclopentanone with TIPS-propargyl fluorophosphonate Example 7 Olefination of Cyclopentanone with TIPS-propargyl fluorophosphonate The reaction was carried out as in Example 2, using cyclopentenone as the carbonyl compound. Obtained in 74percent yield: 1 H NMR (CDCl3) δ 1.10 (apparent s, 21H), 1.68-1.73 (m, 4H), 2.38-2.45 (m, 4H); 19 F NMR δ -114 (s); IR (film, NaCl) v 2960, 2865, 2145, 1675, 1460, 1245, 1155 and 885 cm-1. Patent; University of Massachusetts; US5917074; (1999); (A1) English View in Reaxys

51 %

With formic acid, 3,7-dimethyl10-p-tolyl-5-deazaflavins, Time= 25h, T= 120 °C Yoneda, Fumio; Kuroda, Kazunori; Tanaka, Kiyoshi; Journal of the Chemical Society, Chemical Communications; nb. 17; (1984); p. 1194 - 1195 View in Reaxys

100 % Chromat.

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, silica gel in benzene, Time= 17h, T= 80 °C Nakamura, Kaoru; Fujii, Masayuki; Ohno, Atsuyoshi; Oka, Shinzaburo; Tetrahedron Letters; vol. 25; nb. 36; (1984); p. 3983 - 3986 View in Reaxys

60.3 % Chromat.

With KHBPh3 in tetrahydrofuran, Time= 2h, T= -78 °C Kim, Kwan Eung; Park, Soo Bong; Yoon, Nung Min; Synthetic Communications; vol. 18; nb. 1; (1988); p. 89 - 96 View in Reaxys

51 % Chromat.

With formic acid, 3,7-dimethyl10-p-tolyl-5-deazaflavins, Time= 25h, T= 120 °C Nagamatsu, Tomohisa; Kuroda, Kazunori; Mimura, Norio; Yanada, Reiko; Yoneda, Fumio; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1994); p. 1125 1128 View in Reaxys

13 % Chromat.

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, acetic acid in toluene, Time= 15h, T= 100 °C Inoue, Yoshio; Imaizumi, Shin; Itoh, Hiromitsu; Shinya, Takao; Hashimoto, Harukichi; Miyano, Sotaro; Bulletin of the Chemical Society of Japan; vol. 61; (1988); p. 3020 - 3022 View in Reaxys With hydrogen, silica gel, copper in toluene, Time= 24h, T= 90 °C , p= 760Torr , Yield given Ravasio, Nicoletta; Antenori, Marisa; Gargano, Michele; Mastrorilli, Piero; Tetrahedron Letters; vol. 37; nb. 20; (1996); p. 3529 - 3532 View in Reaxys With hydrogen in propan-1-ol, T= 25 °C , enthalpy of hydrogenation, Thermodynamic data Rogers, Donald W.; Zhao, Yeping; Traetteberg, Marit; Hulce, Martin; Liebman, Joel; Journal of Chemical Thermodynamics; vol. 30; nb. 11; (1998); p. 1393 - 1400 View in Reaxys

87 % Chromat.

With dicobalt octacarbonyl, water in DME, Time= 2h, Heating Lee, Hee-Yoon; An, Mihyun; Tetrahedron Letters; vol. 44; nb. 14; (2003); p. 2775 - 2778 View in Reaxys With 1,3-bis-(diphenylphosphino)propane, caesium carbonate, isopropyl alcohol, bis(1,5-cyclooctadiene)diiridium(I) dichloride in toluene, Time= 4h, T= 80 °C Sakaguchi; Yamaga; Ishii; Journal of Organic Chemistry; vol. 66; nb. 13; (2001); p. 4710 - 4712 View in Reaxys

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With hydrogen, palladium nanoparticles embedded in polysiloxane matrix, T= 120 °C , p= 600.06Torr , Kinetics Trapp, Oliver; Weber, Sven K.; Bauch, Sabrina; Hofstadt, Werner; Angewandte Chemie - International Edition; vol. 46; nb. 38; (2007); p. 7307 - 7310 View in Reaxys > 99 With formic acid, C15H16IrN2O3 (1+)*O4S(2-) in water, Time= 2h, T= 40 °C , pH= 7.3, Inert atmosphere, chemoselective %Chromat. reaction Himeda, Yuichiro; Onozawa-Komatsuzaki, Nobuko; Miyazawa, Satoru; Sugihara, Hideki; Hirose, Takuji; Kasuga, Kazuyuki; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 11076 - 11081 View in Reaxys With old yellow enzyme from Geobacillus kaustophilus, NADPH, Enzymatic reaction Schittmayer, Matthias; Glieder, Anton; Uhl, Michael K.; Winkler, Andreas; Zach, Simone; Schrittwieser, Joerg H.; Kroutil, Wolfgang; MacHeroux, Peter; Gruber, Karl; Kambourakis, Spiros; Rozzell, J. David; Winkler, Margit; Advanced Synthesis and Catalysis; vol. 353; nb. 2-3; (2011); p. 268 - 274 View in Reaxys 2.4. Enzyme assays General procedure: Biotransformation for substrate scope and selectivity analysis were performed in 1 mL reaction volumes consisting of 2 mM NADH and 1 mM substrate, purified enzyme (20 μg) in 20 mM MOPS-NaOH (pH 7.4) with 0.1 M NaCl buffer at 30 °C. Conversions were determined after 5 h of incubation. For GC–MS analysis, reaction mixtures were extracted using an equal volume of ethyl acetate and samples separated on a FactorFour VF-5 ms column (30 m×0.25 mm×0.25 μm, Varian). Chiral separation of the reduction products of R- and S-carvone, 2-methylcyclopentenone and ketoisophorone were performed on a Astec Chiraldex G-TA column (30 m×0.25 mm×0.25 μm, Sigma–Aldrich) and compared to reference activities [37] or the MS fragmentation of diastereomers [38]. For HPLC analysis, reactions were stopped by the addition of 10 μL of concentrated HCl and samples separated on a Jupiter 5 μm C18 300 column (250 mm×4.6 mm, Phenomenex). With ene-reductase from Deinococcus radiodurans, NADH, sodium chloride in aq. buffer, Time= 5h, T= 30 °C , pH= 7.4, Enzymatic reaction, Reagent/catalyst Litthauer; Gargiulo; Van Heerden; Hollmann; Opperman; Journal of Molecular Catalysis B: Enzymatic; vol. 99; (2014); p. 89 - 95 View in Reaxys With Wilkinson's catalyst, hydrogen in toluene, T= 120 °C , p= 1500.15Torr Haywood, Tom; Miller, Philip W.; ChemCatChem; vol. 6; nb. 5; (2014); p. 1199 - 1203 View in Reaxys With xenobiotic reductase A from Pseudomonas putida, NADPH in aq. phosphate buffer, N,N-dimethyl-formamide, Time= 1h, T= 30 °C , pH= 7.5, Enzymatic reaction, Reagent/catalyst Peters, Christin; Koelzsch, Regina; Kadow, Maria; Skalden, Lilly; Rudroff, Florian; Mihovilovic, Marko D.; Bornscheuer, Uwe T.; ChemCatChem; vol. 6; nb. 4; (2014); p. 1021 - 1027 View in Reaxys 96 %Chromat.

With hydrogen in n-heptane, Time= 2h, T= 20 °C , p= 2068.65Torr , Autoclave, chemoselective reaction Natour, Suzana; Abu-Reziq, Raed; RSC Advances; vol. 4; nb. 89; (2014); p. 48299 - 48309 View in Reaxys

97 %Chromat.

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], potassium carbonate, isopropyl alcohol, Time= 5h, T= 85 °C , Inert atmosphere, Schlenk technique, chemoselective reaction Chen, Shu-Jie; Lu, Guo-Ping; Cai, Chun; RSC Advances; vol. 5; nb. 17; (2015); p. 13208 - 13211 View in Reaxys 2.5 Bioreduction of activated alkenes and product analysis General procedure: The bioreduction of various substrates was performed in 1-ml reaction system containing 100mM potassium phosphate buffer (pH 7.0), 10mM NADH, 5mM substrate, and 50μg purified Chr-OYE1 or 500μg purified Chr-OYE2. After 2-min or 16-h incubation at 30°C for Chr-OYE1 and Chr-OYE2, respectively, the reactions were terminated by extraction with ethyl acetate. The organic phase was analyzed using GC or HPLC. (0013) Prepa-

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rative-scale biotransformation was performed in 30-ml reaction system for substrates 4a, 6a, and 12a–17a catalyzed with Chr-OYE1. The incubation was continued for 12h. The extracted organic phase was combined and concentrated under reduced pressure. The final product was purified with column chromatography and subjected to GC or HPLC analysis, as well as NMR analysis to confirm the structure and purity. With Chr-OYE1 (old yellow enzyme from chryseobacterium sp. CA49), β-nicotinamide adenine dinucleotide, oxidized form in aq. phosphate buffer, Time= 0.0333333h, T= 30 °C , pH= 7.0, Enzymatic reaction Pei, Xiao-Qiong; Xu, Meng-Yu; Wu, Zhong-Liu; Journal of Molecular Catalysis B: Enzymatic; vol. 123; (2016); p. 91 - 99 View in Reaxys With enoate reductase YqjM from Bacillus subtilis in ethanol, p= 760.051Torr , Irradiation, Enzymatic reaction Köninger, Katharina; Gómez Baraibar, Álvaro; Mügge, Carolin; Paul, Caroline E.; Hollmann, Frank; Nowaczyk, Marc M.; Kourist, Robert; Angewandte Chemie - International Edition; vol. 55; nb. 18; (2016); p. 5582 - 5585; Angew. Chem.; vol. 55; nb. 128; (2016); p. 5672 - 5675,4 View in Reaxys With old yellow enzyme from Saccharomyces cerevisiae, NADH in aq. buffer, T= 30 °C , pH= 7.5, Enzymatic reaction Turrini, Nikolaus G.; Eger, Elisabeth; Reiter, Tamara C.; Faber, Kurt; Hall, Mélanie; ChemSusChem; vol. 9; nb. 24; (2016); p. 3393 - 3396 View in Reaxys

Rx-ID: 1980284 View in Reaxys 17/449 Yield 100 %

Conditions & References With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 in acetonitrile, Time= 0.0583333h, Heating, Oxidation Minghu, Wu; Guichun, Yang; Zuxing, Chen; Synthetic Communications; vol. 30; nb. 17; (2000); p. 3127 - 3131 View in Reaxys

96 %

With potassium permanganate in water, acetonitrile, Time= 1h, T= 25 °C Wali, Anil; Ganeshpure, Pralhad A.; Satish, Sheo; Bulletin of the Chemical Society of Japan; vol. 66; nb. 6; (1993); p. 1847 - 1848 View in Reaxys

96 %

With dihydrogen peroxide, PFC in acetone, Time= 2.5h, T= 0 - 10 °C Ganguly; Sukai; De; Synthetic Communications; vol. 31; nb. 10; (2001); p. 1607 - 1612 View in Reaxys

95 %

With 1-benzyl-1-aza-4-azoniabicyclolt;2.2.2gt;octane periodate in acetonitrile, Time= 0.25h, Heating, cleavage of oxime double bond under anhydrous conditions; other oximes Hajipour, Abdol Reza; Mahboubghah, Nasrien; Journal of Chemical Research - Part S; nb. 3; (1998); p. 122 - 123 View in Reaxys

95 %

With 1-benzyl-4-aza-1-azoniabiyclolt;2.2.2gt;octane peroxodisulfate in acetonitrile, Time= 0.25h, Heating, Oxidation Hajipour; Mohammadpoor-Baltork; Kianfar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 2; (1999); p. 221 - 224 View in Reaxys

95 %

With benzyltriphenylphosphonium dichromate in acetonitrile, Time= 0.25h, Heating, Oxidation Hajipour, Abdol Reza; Mohammadpoor-Baltork, Iraj; Niknam, Kurosh; Organic Preparations and Procedures International; vol. 31; nb. 3; (1999); p. 335 - 341

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View in Reaxys 95 %

With Cu(NO3)2-SiO2, Time= 0.0166667h, microwave irradiation, oxime cleavage Ghiaci; Asghari; Synthetic Communications; vol. 30; nb. 21; (2000); p. 3865 - 3872 View in Reaxys

94 %

With (cetyl)Me3N(1+)MnO4 (1-) in dichloromethane, Time= 1h, T= 25 °C Vankar, Padma; Rathore, Rajendra; Chandrasekaran, Srinivasan; Journal of Organic Chemistry; vol. 51; nb. 15; (1986); p. 3063 - 3065 View in Reaxys

93 %

Typical Experimental Procedure General procedure: NaClO2 (0.21g, 85percent, 2.0 mmol) was added to a solutionof oxime 1a (0.27g, 2.0 mmol), concentrated HCl (36percent, 2.0mL) in H2O (2.0 mL) in test tube, and the reaction mixturewas stirred at room temperature for 5 min (monitoring with thin-layer chromatography, TLC). The reaction was extractedwith ethyl acetate (10 mL). The combined organicextract was washed with water (5 mL) and dried with anhydrousMgSO4. Then it was directly filtered through a shortsilica gel column (200–300 mesh) to afford the product 2a(0.22 g, 92percent). The carbonyl compounds formed were characterizedby their physical data, which were in accordancewith values reported in the literature, and GC-MS analysis. With hydrogenchloride, sodium chlorite in water, Time= 0.0833333h, T= 20 °C Yao, Yuan-Yuan; Zhao, Xian-Liang; Letters in Organic Chemistry; vol. 12; nb. 1; (2015); p. 73 - 76 View in Reaxys

92 %

With benzyltriphenylphosphonium dichromate, silica gel, Time= 0.0833333h Hajipour; Mallakpour; Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals; vol. 356; (2001); p. 371 - 387 View in Reaxys

90 %

With zeolyte H-Y supported KMnO4 in 1,2-dichloro-ethane, Time= 0.5h, Ambient temperature Jadhav; Wadgaonkar; Joshi; Salunkhe; Synthetic Communications; vol. 29; nb. 11; (1999); p. 1989 - 1995 View in Reaxys

90 %

With water in acetone, Time= 0.0333333h, microwave irradiation Khazaei, Ardeshir; Sadri, Minoo; Hosseini, Hassan; Journal of the Chinese Chemical Society; vol. 54; nb. 4; (2007); p. 1011 - 1015 View in Reaxys

90 %

With N-iodo-succinimide, water in acetone, Time= 0.05h, Microwave irradiation Manesh, Abbas Amini; Khazaei, Ardeshir; Asian Journal of Chemistry; vol. 23; nb. 2; (2011); p. 762 - 764 View in Reaxys

89 %

With sodium perborate in acetic acid, Time= 8h, T= 90 - 95 °C Bandgar; Shaikh; Iyei, Suresh; Synthetic Communications; vol. 26; nb. 6; (1996); p. 1163 - 1168 View in Reaxys

88 %

With ruthenium trichloride, toluene-4-sulfonic acid in N,N-dimethyl acetamide, water, Time= 8h, T= 120 °C , p= 760.051Torr , Inert atmosphere, Green chemistry Liu, Yuxiao; Yang, Na; Chu, Changhu; Liu, Renhua; Chinese Journal of Chemistry; vol. 33; nb. 9; (2015); p. 1011 - 1014 View in Reaxys

87 %

With KMnO4/alumina, Time= 0.25h, T= 50 °C Imanzadeh; Hajipour; Mallakpour; Synthetic Communications; vol. 33; nb. 5; (2003); p. 735 - 740 View in Reaxys

87 %

With chromium trioxide-kieselghur reagent in dichloromethane, Time= 2.5h, Reflux

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Lou, Ji-Dong; Lu, Xiu Lian; Huang, Li-Hong; Zhang, Changhe; Wang, Qiang; Zou, Xiao-Nan; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 41; nb. 10; (2011); p. 1278 - 1281 View in Reaxys 86 %

With water, NBBTA in acetone, Time= 0.05h, Microwave irradiation Manesh, Abbas Amini; Khazaei, Ardeshir; Asian Journal of Chemistry; vol. 23; nb. 2; (2011); p. 624 - 626 View in Reaxys

86 %

With potassium permanganate supported on kieselguhr reagent in dichloromethane, Time= 0.333333h, T= 20 °C , Green chemistry Lou, Ji-Dong; Lin, Fang; Huang, Lihong; Zou, Xiao-Nan; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 42; nb. 7; (2012); p. 1027 - 1029 View in Reaxys

86 %

in dichloromethane, Time= 4.5h, T= 20 °C Lin, Fang; Lin, Jianan; Zheng, Wenjin; Lu, Xiu Lian; Lou, Ji-Dong; Synthesis and Reactivity in Inorganic, MetalOrganic and Nano-Metal Chemistry; vol. 43; nb. 10; (2013); p. 1518 - 1520 View in Reaxys

86 %

With manganese(IV) oxide in neat (no solvent), Time= 0.0333333h, T= 20 °C Zheng, Wenjin; Huang, Chen; Zhang, Changhe; Zhou, Yi-Feng; Lou, Ji-Dong; Research on Chemical Intermediates; vol. 39; nb. 2; (2013); p. 499 - 504 View in Reaxys

85 %

With hydrogenchloride in water, acetonitrile, Time= 0.0333333h, microwaver irradiation Anniyappan, Marimuthu; Muralidharan; Perumal, Paramasivan T.; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 41; nb. 11; (2002); p. 2419 - 2420 View in Reaxys

85 %

With (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, oxygen, benzaldehyde in toluene, Time= 8h, T= 50 °C Zhou, Xian-Tai; Yuan, Qiu-Lan; Ji, Hong-Bing; Tetrahedron Letters; vol. 51; nb. 4; (2010); p. 613 - 617 View in Reaxys

85 %

With Jones reagent supported on Kieselguhr in dichloromethane, Time= 1.5h, T= 20 °C Lou, Ji-Dong; Lin, Fang; Lu, Xiu Lian; Wang, Qiang; Zou, Xiao-Nan; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 42; nb. 2; (2012); p. 282 - 284 View in Reaxys

85 %

With toluene-4-sulfonic acid, Time= 0.0166667h, T= 20 °C , neat (no solvent) Dewan, Anindita; Utpal Bora; Dilip K. Kakati; Bulletin of the Korean Chemical Society; vol. 32; nb. 7; (2011); p. 2482 - 2484 View in Reaxys

82 %

With vanadium(III) chloride in tetrahydrofuran, Time= 8h, Ambient temperature Olah, George A.; Arvanaghi, Massoud; Prakash, G.K. Surya; Synthesis; nb. 3; (1980); p. 220 View in Reaxys

82 %

With antimonypentachloride in dichloromethane, Time= 2.3h, T= 20 °C Narsaiah, A. Venkat; Nagaiah; Synthesis; nb. 12; (2003); p. 1881 - 1882 View in Reaxys

82 %

With potassium permanganate in neat (no solvent), Time= 0.166667h, T= 20 °C , Milling Zhu, Li-Yun; Lou, Zhiyuan; Lin, Jianan; Zheng, Wenjin; Zhang, Changhe; Lou, Ji-Dong; Research on Chemical Intermediates; vol. 39; nb. 9; (2013); p. 4315 - 4320 View in Reaxys

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81 %

With potassium sulfate, potassium hydrogensulfate, oxone, acetic acid in water, Time= 2h, T= 40 - 45 °C Bose, D. Subhas; Srinivas; Synthetic Communications; vol. 27; nb. 22; (1997); p. 3835 - 3838 View in Reaxys

81 %

With hexamethylenetetramine; hydrobromide, Time= 0.0333333h, T= 20 °C , Hydrolysis Bandgar; Makone; Organic Preparations and Procedures International; vol. 32; nb. 4; (2000); p. 391 - 394 View in Reaxys

79 %

With aluminium trichloride, 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate, Time= 0.00833333h, T= 20 °C Hajipour; Mallakpour; Mohammadpoor-Baltork; Khoee; Synthetic Communications; vol. 31; nb. 8; (2001); p. 1187 - 1194 View in Reaxys

79 %

With oxygen, sodium nitrite in dichloromethane, water, Time= 7h, T= 25 °C , p= 760.051Torr , Sealed system Zhang, Guofu; Wen, Xin; Wang, Yong; Mo, Weimin; Ding, Chengrong; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4665 - 4668 View in Reaxys

78 %

2.4. General Procedure for the Oxidation under Microwave Irradiation General procedure: The substrate (1mmol) and 1.5–2 mmol oxidant were mixed. To this mixture 0.5 mL CH2Cl2 was added. The mixture was subjected to microwave irradiation (1000 W). Upon completion of the reaction, extraction with ether (3 × 25mL) and evaporation of the solvent gave the corresponding carbonyl compounds. The products formed were analyzed by their 2,4-dinitrophenylhydrazone derivatives.The precipitated 2,4-DNP was filtered off, weighed, and recrystallized from ethanol. With TMGFC in dichloromethane, Time= 0.00277778h, Microwave irradiation, Reagent/catalyst Şendil, Kivilcim; Özgün, H. Beytiye; Üstün, Ebru; Journal of Chemistry; vol. 2016; (2016); Art.No: 3518102 View in Reaxys

75 %

With sodium hydroxide, dihydrogen peroxide in methanol, Heating Ho, Tse-Lok; Synthetic Communications; vol. 10; nb. 6; (1980); p. 465 - 468 View in Reaxys

67 %

With N-Bromosuccinimide in water, acetone, Time= 2.5h, T= 25 °C Bandgar, Babasaheb P.; Kale, Ramesh R.; Kunde, Lalita B.; Monatshefte fur Chemie; vol. 129; nb. 10; (1998); p. 1057 - 1060 View in Reaxys

42 %

With ziconium(IV) oxychloride octahydrate in water, acetone, Time= 7h, Reflux Saikia, Lakhinath; Das, Subrata; Thakur, Ashim Jyoti; Synthetic Communications; vol. 41; nb. 7; (2011); p. 1071 - 1076 View in Reaxys

41 %

oxidative deoximation of oximes General procedure: To a solution of p-chlorobenzaldoxime (3 mmol, 0.468 g) in chloroform (9 mL),dehydrated Ce(SO4)2 (9 mmol, 2.998 g) was added and the reaction mixturestirred at room temperature for 15 min. The mixture was filtered through asintered glass funnel and the organic solvent evaporated. Besides pchlorobenzaldehyde(19percent), 3,5-bis(4-chlorophenyl)-1,2,4-oxadiazole and 1-chloro-4-(dinitromethyl)benzene were also isolated in 3percent and 7percent yields,respectively after column chromatography. With cerium(IV) sulphate in chloroform, Time= 2.33333h, T= 20 °C Asutay, Oktay; Hamarat, Nilüfer; Uludag, Nesimi; Coşkun, Necdet; Tetrahedron Letters; vol. 56; nb. 25; (2015); p. 3902 - 3904 View in Reaxys With bis(trimethylsilyl)chromate in dichloromethane, Time= 18h, Ambient temperature, other oximes, var. time, Product distribution

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Lee; Kwak; Hwang; Synthetic Communications; vol. 22; nb. 16; (1992); p. 2425 - 2429 View in Reaxys With aluminum oxide, Me3NHCrO3Cl in dichloromethane, Time= 7h, T= 38 °C , Yield given Zhang, Gui-Sheng; Yang, De-Hong; Chen, Mi-Feng; Organic Preparations and Procedures International; vol. 30; nb. 6; (1998); p. 713 - 716 View in Reaxys With dimethylammonium chlorochromate, silica gel in diethyl ether, dichloromethane, Time= 5.5h, T= 38 - 40 °C Zhang, Gui-Sheng; Chai, Bing; Synthetic Communications; vol. 30; nb. 10; (2000); p. 1849 - 1855 View in Reaxys 40 % Chromat.

With chloranil in acetonitrile, Time= 8h, Irradiation De Lijser, H. J. Peter; Fardoun, Fadia H.; Sawyer, Jody R.; Quant, Michelle; Organic Letters; vol. 4; nb. 14; (2002); p. 2325 - 2328 View in Reaxys

87 %Chromat.

With MnTEPyP, dihydrogen peroxide in water, acetone, Time= 2.5h, T= 60 °C Ren, Qing-Gang; Zhou, Xian-Tai; Ji, Hong-Bing; Journal of Porphyrins and Phthalocyanines; vol. 15; nb. 3; (2011); p. 211 - 216 View in Reaxys With 3,5-dimethylpyrazolium chlorochromate, Time= 0.0166667h, T= 20 °C , Neat (no solvent) Canbulat, Melek; Oezguen, Beytiye; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 42; nb. 5; (2012); p. 634 - 637 View in Reaxys

N HN O

Rx-ID: 3778419 View in Reaxys 18/449 Yield

Conditions & References

82 %

With lithium perchlorate in water, acetonitrile, T= 25 °C , electrolysis Lin, En-Chu; Mark, Michael R. Van De; Journal of the Chemical Society, Chemical Communications; nb. 20; (1982); p. 1176 - 1178 View in Reaxys

81 %

General procedure for the cleavage of hydrazones by bismuth oxychloride: General procedure: A solution of the hydrazone (1 mmol) in acetonitrile (10 mL) was refluxed for 10 min.Then BiOCl (1 mmol) was added to the solution and the mixture was refluxed for theappropriate time, as indicated in Table I. After completion of the reaction (TLC monitored),the reaction mixture was cooled to room temperature and H2O (1 mmol) was added and themixture stirred for 10 min. Then the solvent was evaporated and CHCl3 or THF was added.After stirring the mixture for 10 min, the solid residue was filtered off and washed with CHCl3or THF (10 mL). Evaporation of the solvent gave the pure carbonyl products in excellentyields. With bismuth (III) oxychloride in water, acetonitrile, Time= 1.25h, Reflux Manesh, Abbas Amini; Azarin, Khadijeh; Journal of the Serbian Chemical Society; vol. 81; nb. 2; (2016); p. 125 131 View in Reaxys O

Rx-ID: 5929728 View in Reaxys 19/449

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Yield 72.6%

Conditions & References C.2 : Comparative Example 2 Comparative Example 2 Example 1 was repeated except that the catalyst used was prepared in the same manner as in Reference Example 1 except that the reduction with hydrogen gas was not conducted. Yield of 2-cyclopentenone in the reaction mixture was 2.2percent and selectivity was 2.9percent. Principal product was cyclopentanone (yield 72.6percent). Patent; Nippon Zeon Co., Ltd.; US5118862; (1992); (A1) English View in Reaxys

69 %

Example 16 : Examples 3 to 16 General procedure: Photocatalyst (Ru (bpy) 3Cl2) was prepared in the amine-based compound, a 1 molpercentconcentration of the oxidizing agent (K2S2O8) and solvent (0.1 M, CH3CN / H2O (1/1))under the condition, the blue light-emitting diode in the power consumption 7W was a12-hour reaction at room temperature using. With the selected amine compound wasanalyzed and the manufactured product are shown in Table 2 below Yield of the product was measured by gas chromatography using a dodecane (dodecane)as an internal standard method With dipotassium peroxodisulfate, tris(2,2'-bipyridyl)ruthenium dichloride in water, acetonitrile, Time= 12h, T= 20 °C , Irradiation Patent; Chung-Ang University Academic Cooperation; Jo, Uhn Jin; Nadim, Iqbal; (15 pag.); KR101609985; (2016); (B1) Korean View in Reaxys

57 %

10 Patent; JX Nippon Oil and Energy Corporation; EP2364965; (2011); (A1) English View in Reaxys

57 %

10 Patent; JX NIPPON OIL and ENERGY CORPORATION; US2011/288340; (2011); (A1) English View in Reaxys Herstellung von <1-14 C>Cyclopentanon Brooks; Journal of the Chemical Society; (1958); p. 3693,3695 View in Reaxys Herstellung von <1,2-14 C 2>Cyclopentanon Loftfield; ; (1958); p. 654 View in Reaxys Wiloth,F.; Schindler,E.; Chemische Berichte; vol. 100; (1967); p. 2373 - 2376 View in Reaxys Bestmann,H.J.; Kranz,E.; Chemische Berichte; vol. 102; (1969); p. 1802 - 1815 View in Reaxys Mihailovic,M.L. et al.; Tetrahedron; vol. 24; (1968); p. 4947 - 4961 View in Reaxys Omura,K.; Swern,D.; Tetrahedron; vol. 34; (1978); p. 1651 - 1660 View in Reaxys Singh,R.P. et al.; Tetrahedron; vol. 35; (1979); p. 1789 - 1793 View in Reaxys Rabiller,C. et al.; Bulletin de la Societe Chimique de France; (1974); p. 3055 - 3058 View in Reaxys Yamamoto,Y.; Brown,H.C.; Journal of the Chemical Society, Chemical Communications; (1973); p. 801 - 802 View in Reaxys Greene,F.D. et al.; Journal of Organic Chemistry; vol. 28; (1963); p. 55 - 64 View in Reaxys Hermes,M.E.; Marsh,F.D.; Journal of Organic Chemistry; vol. 37; nb. 19; (1972); p. 2969 - 2979 View in Reaxys Binkley,R.W.; Journal of Organic Chemistry; vol. 41; (1976); p. 3030 - 3031

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View in Reaxys Girard,C. et al.; Tetrahedron Letters; (1974); p. 3329 - 3332 View in Reaxys Ogura,K. et al.; Tetrahedron Letters; (1975); p. 2767 - 2770 View in Reaxys Masuyama,Y. et al.; Tetrahedron Letters; (1976); p. 2967 - 2970 View in Reaxys Ogibin; Troyanskii; Nikishin; Bulletin of the Academy of Sciences of the USSR Division of Chemical Science; vol. 26; nb. 4; (1977); p. 767 - 771 View in Reaxys Delmond, Bernard; Pommier, Jean-Claude; Valade, Jacques; Journal of Organometallic Chemistry; vol. 35; nb. 1; (1972); p. 91 - 104 View in Reaxys Foerster,C. et al.; Journal fuer Praktische Chemie (Leipzig); vol. 311; (1969); p. 370 - 378 View in Reaxys House; Babad; Journal of Organic Chemistry; vol. 28; (1963); p. 90 View in Reaxys Marsh; Hermes; Journal of the American Chemical Society; vol. 86; (1964); p. 4506 View in Reaxys Jaz; Davreux; Bulletin des Societes Chimiques Belges; vol. 74; (1965); p. 370 View in Reaxys Flatt et al.; Synthesis; (1979); p. 815 View in Reaxys Bestmann; Kranz; Angewandte Chemie; vol. 79; (1967); p. 95 View in Reaxys Nelson et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 1580 View in Reaxys Huet et al.; Synthesis; (1978); p. 63 View in Reaxys Giannotti; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 258; (1964); p. 5225 View in Reaxys Holum; Journal of Organic Chemistry; vol. 26; (1961); p. 4814,4815 View in Reaxys Pratt; van de Castle; Journal of Organic Chemistry; vol. 26; (1961); p. 2973 View in Reaxys Maloney; Lyle; Saavedra; Synthesis; vol. No. 3; (1978); p. 212 - 213 View in Reaxys Cella et al.; Journal of Organic Chemistry; vol. 40; (1975); p. 1860 View in Reaxys Kuehne; Hall; Journal of Organic Chemistry; vol. 41; (1976); p. 2742 View in Reaxys Mowsumsade et al.; Azerbaidzhanskii Khimicheskii Zhurnal; vol. 6; (1969); p. 86,88; ; vol. 74; nb. 53112; (1971) View in Reaxys Huang et al.; Synthesis; (1978); p. 297 View in Reaxys Franzen; Otto; Chemische Berichte; vol. 94; (1961); p. 1360,1363 View in Reaxys Heyns; Blazejewicz; Tetrahedron; vol. 9; (1960); p. 67,73 View in Reaxys Allen et al.; Journal of the Chemical Society; (1960); p. 1909,1911 View in Reaxys Maynez et al.; Journal of Organic Chemistry; vol. 40; (1975); p. 3302 View in Reaxys Olah; Ho; Synthesis; (1976); p. 610 View in Reaxys Turowa-Poljak et al.; Neftekhimiya; vol. 4; (1964); p. 603; ; p. 240 View in Reaxys Boldrini et al.; Synthesis; (1976); p. 596 View in Reaxys Hintz; Johnson; Journal of Organic Chemistry; vol. 32; (1967); p. 556,558 View in Reaxys

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Sacks; Fuchs; Synthesis; (1976); p. 456 View in Reaxys Boontanonda; Grigg; Journal of the Chemical Society, Chemical Communications; (1977); p. 583 View in Reaxys Jung et al.; Tetrahedron Letters; (1977); p. 4175,4177 View in Reaxys Townsend; Spencer; Tetrahedron Letters; (1971); p. 137,138 View in Reaxys Borowitz et al.; Tetrahedron Letters; (1971); p. 105,106 View in Reaxys Cella et al.; Tetrahedron Letters; (1975); p. 4115 View in Reaxys Tufariello; Kissel; Tetrahedron Letters; (1966); p. 6145,6147 View in Reaxys Liu; Lai; Tetrahedron Letters; (1979); p. 1193,1195 View in Reaxys Abley et al.; Journal of the American Chemical Society; vol. 32; (1976); p. 2591,2592-2594 View in Reaxys Greene et al.; Tetrahedron Letters; (1976); p. 2707 View in Reaxys Patent; Deutsche Advance Prod.; BE615018; (1962); DE; ; vol. 57; nb. 14941; (1962) View in Reaxys Fujihara et al.; Yukagaku; vol. 24; (1975); p. 654,657; ; vol. 84; nb. 59755n View in Reaxys Olah et al.; Synthesis; (1979); p. 274 View in Reaxys Blackburn; Schwartz; Journal of the Chemical Society, Chemical Communications; (1977); p. 157 View in Reaxys Liberman et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 20; (1971); p. 1809,1811; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 20; (1971); p. 1917 View in Reaxys Collman; Accounts of Chemical Research; vol. 8; (1975); p. 342,343, 344 View in Reaxys Cortese; Heck; Journal of Organic Chemistry; vol. 43; (1978); p. 3985,3987 View in Reaxys Sheikh; Eadon; Tetrahedron Letters; (1972); p. 257,258,259 View in Reaxys Leriverend; Leriverend; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 280; (1975); p. 791 View in Reaxys Price; Iwasa; Bulletin of the Chemical Society of Japan; vol. 49; (1976); p. 214,215, 216 View in Reaxys Olah et al.; Synthesis; (1979); p. 113 View in Reaxys Schroeder; Griffith; Journal of the Chemical Society, Chemical Communications; (1979); p. 58 View in Reaxys Ryang et al.; Bulletin of the Chemical Society of Japan; vol. 37; (1964); p. 1704 View in Reaxys Minatschew et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1964); p. 10; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1964); p. 13 View in Reaxys Jaworski; Kwiatkowski; Roczniki Chemii; vol. 48; (1974); p. 263,268 View in Reaxys Liberman et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 20; (1971); p. 1423,1427; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 20; (1971); p. 1527 View in Reaxys Cookson et al.; Chemical Communications (London); (1966); p. 744 View in Reaxys Liberman et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 21; (1972); p. 1942; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 21; (1972); p. 2001 View in Reaxys

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Forbus et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 6425 View in Reaxys Nakai et al.; Bulletin of the Chemical Society of Japan; vol. 42; (1969); p. 2917,2918 View in Reaxys Hofmann; Angewandte Chemie; vol. 77; (1965); p. 346 View in Reaxys Liberman; Vasina; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1968); p. 609,610,611; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1968); p. 632 View in Reaxys Fal'kowskii et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 36; (1963); p. 230,218 View in Reaxys Lewina et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 359,383; ; vol. 54; nb. 24457; (1960) View in Reaxys Ho; Synthetic Communications; vol. 9; (1979); p. 237 View in Reaxys Rajan et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 17; (1979); p. 80 View in Reaxys Tsuji; Ohno; Journal of the American Chemical Society; vol. 90; (1968); p. 94 View in Reaxys Moon; Waxman; Journal of Organic Chemistry; vol. 34; (1969); p. 1157 View in Reaxys Crouzet et al.; Bulletin de la Societe Chimique de France; (1967); p. 4047 View in Reaxys Delmond; Pommier; Tetrahedron Letters; (1968); p. 6147 View in Reaxys Bird; Diaper; Canadian Journal of Chemistry; vol. 47; (1969); p. 145 View in Reaxys Corey; Achiwa; Journal of the American Chemical Society; vol. 91; (1969); p. 1429 View in Reaxys Brown; Ritchie; Journal of the Chemical Society [Section] C: Organic; (1968); p. 2007 View in Reaxys Pearson; Moss; Tetrahedron Letters; (1967); p. 3791 View in Reaxys Brown; Hess; Journal of Organic Chemistry; vol. 34; (1969); p. 2206 View in Reaxys Richer; Nguyen Thi Thanh Hoa; Canadian Journal of Chemistry; vol. 47; (1969); p. 2479 View in Reaxys Wahlroos; Enkvist; Acta Chemica Scandinavica (1947-1973); vol. 22; (1968); p. 3202,3206 View in Reaxys Schwall et al.; Chemische Berichte; vol. 102; (1969); p. 1731 View in Reaxys 7 : The Cyclopentanone 20 The Cyclopentanone 20 Methylmagnesium chloride (22.5 ml of a 3M solution in ether, 67.5 mmol) was added slowly to a stirred solution of dimethylzinc (16.9 ml of a 2M solution in toluene, 33.8 mmol) in THF (100 ml) under argon at 0° C. After 30 minutes the mixture was cooled to -78 ° C. and 19 (3.37 g, 30.6 mmol) in THF (45 ml) was added dropwise over 1 hour. The reaction mixture was stirred for 20 minutes and then quenched by the addition of saturated ammonium chloride solution (25 ml). The reaction mixture was allowed to warm to room temperature, diluted with 1N hydrochloric acid (100 ml) and extracted with ether (3*100 ml). The organic layer was washed with brine (50 ml), dried (MgSO4) and the solvent was removed under reduced pressure to yield 20 as a solution in toluene which was purified by column chromatography (SiO2, pentane-ether, 95:5) to give the cyclopentanone 20 (2.4 g, 62percent). δH(400 MHz; CDCl3) 2.50-2.40 (2H, m), 1.92-1.60 (6H, m), 1.12 (3H, d, J 6.1, Me), 0.93 (3H, t, J 6.5, Me). Patent; Blakemore, David Clive; Bryans, Justin Stephen; US2003/187296; (2003); (A1) English View in Reaxys

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Exemplary of such ketones, the following are representative: Cyclopentanone; 2-Methylcyclohexanone; 2-Methylcyclopentanone; 2,5-Dimethylcyclopentanone; 2,6-Dimethylcyclohexanone; and 2-Phenylcyclohexanone. Patent; Rhone-Poulenc Chimie; US4983767; (1991); (A1) English View in Reaxys Suitable charge stock compounds include the following without being limited, thereto, cyclohexanol, cyclohexanone, cyclohexanol, cyclohexanone, ... 1,4-cyclohexanedione, 4-methylcyclohexanone, 3,5-dimethylcyclohexanone, 4-phenylcyclohexanone, cyclopentanone, 3-methylcyclopentanol, 2-ketotetralin, 2-(1-cyclohexenyl)cyclohexanone, Patent; Standard Oil Company; US4271091; (1981); (A1) English View in Reaxys methyl ethyl ketone ... amyl acetate neopentyl acetate propyl propionate t-butyl propionate cyclopentanone Patent; Eli Lilly and Company; US4303591; (1981); (A1) English View in Reaxys Suitable charge stock compounds include the following without being limited, thereto, cyclohexanol, cyclohexanone, cyclohexanol, cyclohexanone, ... 4-methylcyclohexanone, 3,5-dimethylcyclohexanone, 4-phenylcyclohexanone, cyclopentanol, cyclopentanone, 3-methylcyclopentanol, 2-(1-cyclohexenyl)cyclohexanone, Patent; The Standard Oil Co.; US4379925; (1983); (A1) English View in Reaxys Representative aldehydes and ketones include: formaldehyde ... methyl propyl ketone methyl butyl ketone methyl isobutyl ketone

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methyl tert-butyl ketone cyclopentanone cyclooctanone Patent; Eli Lilly and Company; US4501608; (1985); (A1) English View in Reaxys 57 : EXAMPLE 57 EXAMPLE 57 Experiment was carried out in the same manner as in Example 54 except that the reaction temperature was raised from 50° C. up to 80° C., to obtain 3.2 g of cyclopentanone at a reaction time of 15 minutes. Patent; Babcock-Hitachi Kabushiki Kaisha; US4806692; (1989); (A1) English View in Reaxys 58 : EXAMPLE 58 EXAMPLE 58 Experiment was carried out in the same manner as in Example 54 except that the concentration of Cu(1)Cl was raised from 0.2 M up to 0.5 M, to obtain 3.0 g of cyclopentanone at a reaction time of 20 minutes. Patent; Babcock-Hitachi Kabushiki Kaisha; US4806692; (1989); (A1) English View in Reaxys 60 : EXAMPLE 60 EXAMPLE 60 Experiment was carried out in the same manner as in Example 55 except that Cu(1)Cl (0.2 M) was replaced by Ti(3)CH3 (0.2 M) to obtain 0.61 g of cyclopentanone in 30 minutes. Patent; Babcock-Hitachi Kabushiki Kaisha; US4806692; (1989); (A1) English View in Reaxys 61 : EXAMPLE 61 EXAMPLE 61 Experiment was carried out in the same manner as in Example 55 except that Cu(1)Cl (0.2 M) was replaced by V(3)Cl3 (0.2 M) to obtain 0.72 g of cyclopentanone in 30 minutes. Patent; Babcock-Hitachi Kabushiki Kaisha; US4806692; (1989); (A1) English View in Reaxys 62 : EXAMPLE 62 EXAMPLE 62 Experiment was carried out in the same manner as in Example 54 except that CH3 CN was replaced by PhCN to obtain 0.95 g of cyclopentanone at a reaction time of one hour. Patent; Babcock-Hitachi Kabushiki Kaisha; US4806692; (1989); (A1) English View in Reaxys 63 : EXAMPLE 63 EXAMPLE 63 Experiment was carried out in the same manner as in Example 62 except that the concentration of Cu(1)Cl was raised from 0.2 M up to 0.6 M to obtain 1.2 g of cyclopentanone in 30 minutes. Patent; Babcock-Hitachi Kabushiki Kaisha; US4806692; (1989); (A1) English View in Reaxys 8 : Preparation of 2-carboxyhexyl)cyclopentan-1-one EXAMPLE 8 Preparation of 2-carboxyhexyl)cyclopentan-1-one In the manner described in Example 2, ethyl and methyl 2-(6-carbethoxyhexyl)-1-cyclopentanone-2-carboxylate (Example 7) is hydrolyzed to furnish the subject product, b.p. 143° C. (0.05 mm). Patent; American Cyanamid Company; US4061672; (1977); (A1) English View in Reaxys 6 : Preparation of 2-(3-carbethoxyropyl)cyclopentan-1-one EXAMPLE 6

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Preparation of 2-(3-carbethoxyropyl)cyclopentan-1-one In the manner described in Example 3, treatment of 2-(3-carboxypropyl)cyclopentan-1-one (Example 5) with p-toluene-sulfonic acid monohydrate in ethanol gives a colorless oil, b.p. 93° C. (0.10 mm). Patent; American Cyanamid Company; US4110368; (1978); (A1) English View in Reaxys 57 : Example 57 Example 57 Experiment was carried out in the same manner as in Example 54 except that the reaction temperature was raised from 50°C up to 80°C, to obtain 3.2 g of cyclopentanone at a reaction time of 15 minutes. Patent; BABCOCK-HITACHI KABUSHIKI KAISHA; EP189312; (1991); (B1) English View in Reaxys 58 : Example 58 Example 58 Experiment was carried out in the same manner as in Example 54 except that the concentration of Cu(1)C was raised from 0.2 M up to 0.5 M, to obtain 3.0 g of cyclopentanone at a reaction time of 20 minutes. Patent; BABCOCK-HITACHI KABUSHIKI KAISHA; EP189312; (1991); (B1) English View in Reaxys 60 : Example 60 Example 60 Experiment was carried out in the same manner as in Example 55 except that Cu(1)C (0.2 M) was replaced by Ti(3)C3 (0.2 M) to obtain 0.61 g of cyclopentanone in 30 minutes. Patent; BABCOCK-HITACHI KABUSHIKI KAISHA; EP189312; (1991); (B1) English View in Reaxys 61 : Example 61 Example 61 Experiment was carried out in the same manner as in Example 55 except that Cu(1)C (0.2 M) was replaced by V(3)C3 (0.2 M) to obtain 0.72 g of cyclopentanone in 30 minutes. Patent; BABCOCK-HITACHI KABUSHIKI KAISHA; EP189312; (1991); (B1) English View in Reaxys 62 : Example 62 Example 62 Experiment was carried out in the same manner as in Example 54 except that CH3CN was replaced by PhCN to obtain 0.95 g of cyclopentanone at a reaction time of one hour. Patent; BABCOCK-HITACHI KABUSHIKI KAISHA; EP189312; (1991); (B1) English View in Reaxys 63 : Example 63 Example 63 Experiment was carried out in the same manner as in Example 62 except that the concentration of Cu(1)C was raised from 0.2 M up to 0.6 M to obtain 1.2 g of cyclopentanone in 30 minutes. Patent; BABCOCK-HITACHI KABUSHIKI KAISHA; EP189312; (1991); (B1) English View in Reaxys 1 : Synthesis of Astrogorgiadiol This substance was not stable to analysis by mass spectrometry. Methyl 5-Dimethylhexenyl-2-oxocyclopentanecarboxylate (2) via Rh2Oct4 Catalysis: The CH2Cl2 used in the following reaction was distilled from CaH2 and passed through a column (20*150 mm) of anhydrous K2CO3 prior to use. The α-diazo-β-ketoester 1 (25.5 g, 101 mmol) was dissolved in 1 L CH2Cl2. A solution of rhodium octanoate (400 mg, 0.56 mol percent) in 5 mL dry CH2Cl2 was added in one portion. The solution was allowed to stir for 12 hours before being evaporated. The green residue was chromatographed to provide cyclopentanone 2 (17.0 g, 74percent) as a light-green oil. Bulbto-bulb distillation (170° C. at 0.4 mm Hg) yielded a clear oil which formed moist crystals on standing.

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These did not show a sharp melting point. TLC Rf(10percent MTBE/petroleum ether)=0.28. 1H NMR (CDCl3) (δ): 5.06 (m, 1H), 3.75 (s, 3H), 2.97 (d, J=11.6 Hz, 0.43H), 2.95 (d, J=11.3 Hz, 0.57H), 2.55 (m, 1H), 2.5-2.3 (m, 2H), 2.3-1.9 (m, 3H), 1.69 (s, 3H), 1.61 (s, 3H), 1.6-1.3 (m, 3H), 1.17 (m, 1h), 0.93 (d, J=6.83 Hz, 1.3H), 0.91 (d, J=6.85 Hz, 1.7H); 13C NMR (CDCl3) (δ): (Major) u: 212.4, 170.7, 131.7, 38.7, 33.8, 25.3, 25.1; d: 124.2, 59.6, 52.4, 46.7, 36.8, 25.7, 17.6, 16.9; 13C NMR (CDCl3) (δ): (Minor) u: 212.2, 170.3, 131.6, 38.5, 33.8, 25.3, 25.1; d: 124.1, 59.7, 52.4, 46.3, 35.7, 25.7, 15.5, 16.9; IR (cm-1): 3447 (br), 2966, 1757, 1726. Patent; Taber, Douglass F.; Farach-Carson, Mary C.; Malcolm, Scott C.; Xu, Yihuan; US2004/242677; (2004); (A1) English View in Reaxys

Rx-ID: 28655094 View in Reaxys 20/449 Yield

Conditions & References 1 :In a 350-ml autoclave made of stainless steel SUS 316 and equipped with a stirrer were placed 80 g (1.14 mol) of cyclopentane and 2 g of a 5 percent by weight N-hydroxysuccinimide aqueous solution which contained 100 mg of N-hydroxysuccinimide dissolved therein, at room temperature (25°C). The autoclave was hermetically sealed, pressurized to 3 MPa (gauge pressure) with a gaseous mixture of 50 percent by volume oxygen and 50 percent by volume nitrogen, and the aqueous solution therein was stirred at 150°C for 1 hour. As a result, 39 mmol of cyclopentane reacted (with a conversion of 3.4percent) and thereby yielded 9.4 mmol of cyclopentanone (with a selectivity of 24.1percent), 4.8 mmol of cyclopentanol (with a selectivity of 12.3percent), and 12.5 mmol of cyclopentyl hydroperoxide (with a selectivity of 32.1percent). The total yield of cyclopentanone, cyclopentanol, and cyclopentyl hydroperoxide was 2.3percent. With 1-hydroxy-pyrrolidine-2,5-dione, oxygen in water, T= 25 - 150 °C , p= 22502.3Torr , autoclave, Product distribution / selectivity Patent; DAICEL CHEMICAL INDUSTRIES, LTD.; EP2096097; (2009); (A1) English View in Reaxys

32 %Chromat., 28 %Chromat., 7 %Chromat.

Stage 1: With [CuI(tris(2-pyridylmethyl)amine)(CH3CN)](PF6), dihydrogen peroxide in water, acetonitrile, Time= 6h, T= 20 °C Stage 2: With triphenylphosphine, Time= 0.333333h, Cooling with ice, Reagent/catalyst Garcia-Bosch, Isaac; Siegler, Maxime A.; Angewandte Chemie - International Edition; vol. 55; nb. 41; (2016); p. 12873 - 12876; Angew. Chem.; vol. 128; nb. 41; (2016); p. 13065 - 13068,4 View in Reaxys

Rx-ID: 36338213 View in Reaxys 21/449 Yield

Conditions & References With water, hydrogen, T= 160 °C , p= 30003Torr , Autoclave Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys With palladium on activated charcoal, hydrogen in water, Time= 1h, T= 159.84 °C , p= 37503.8Torr , Reagent/catalyst Li, Guangyi; Li, Ning; Zheng, Mingyuan; Li, Shanshan; Wang, Aiqin; Cong, Yu; Wang, Xiaodong; Zhang, Tao; Green Chemistry; vol. 18; nb. 12; (2016); p. 3607 - 3613 View in Reaxys

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O O O

Rx-ID: 36338225 View in Reaxys 22/449 Yield

Conditions & References

31 %, 69 %

With hydrogen in water, Time= 1.2h, T= 160 °C , p= 30003Torr , Autoclave Zhang, Gao-Shuo; Zhu, Ming-Ming; Zhang, Qi; Liu, Yong-Mei; He, He-Yong; Cao, Yong; Green Chemistry; vol. 18; nb. 7; (2016); p. 2155 - 2164 View in Reaxys With water, hydrogen, T= 160 °C Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys Reaction Steps: 2 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water / 160 °C / |Autoclave With water, hydrogen, sodium carbonate Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys With hydrogen in water, Time= 6h, T= 149.84 °C , p= 30003Torr , Autoclave, Reagent/catalyst, chemoselective reaction Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao; Green Chemistry; vol. 17; nb. 2; (2015); p. 1038 - 1046 View in Reaxys With hydrogen in water, Time= 1h, T= 169.84 °C , p= 15001.5Torr , Autoclave, Reagent/catalyst, Temperature, chemoselective reaction Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao; Green Chemistry; vol. 17; nb. 2; (2015); p. 1038 - 1046 View in Reaxys O

O OH

Rx-ID: 36338235 View in Reaxys 23/449 Yield

Conditions & References

66.1 %, 9.4 %

With water, zinc, Time= 2.33333h, T= 250 °C , Autoclave Ren, Dezhang; Song, Zhiyuan; Li, Lu; Liu, Yunjie; Jin, Fangming; Huo, Zhibao; Green Chemistry; vol. 18; nb. 10; (2016); p. 3075 - 3081 View in Reaxys With water, hydrogen, T= 160 °C , Autoclave Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys OH

O OH

Rx-ID: 36338236 View in Reaxys 24/449

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Yield

Conditions & References With pentanal, water, hydrogen, Time= 4h, T= 160 °C , p= 30003Torr , Autoclave Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys With water, hydrogen, benzaldehyde, Time= 4h, T= 160 °C , p= 30003Torr , Autoclave Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys Reaction Steps: 2 1: hydrogen; water / 8 h / 160 °C / |Inert atmosphere; |Autoclave 2: hydrogen; water / 160 °C / 30003 Torr / |Autoclave With water, hydrogen Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys General procedure: Catalytic experiments were performed using procedure and analytical methods described in our previous paper [14]. For a typical reaction, 20 ml of water, 0.5–1.0 g of reactant and given amount of metal catalyst was added to the reactor vessel. After sealing the reactor was several times flushed with low pressure hydrogen and then pressurized with hydrogen usually to 30–80 bar (ambient temperature). The reactor was then heated to the desired temperature and the stirring speed adjusted to 1500 rpm to eliminate external mass-transfer effects. After an appropriate reaction timethe reactor was quickly cooled down, the reactor contents pour out to vial and the catalyst separated from the aqueous phase by centrifugation. The quantitative determination of the liquid products concentration was done using gas chromatography by the external standard method and using response factors of the corresponding standard compounds. A gas chromatograph–mass spectrometer combination was used to identify the organic compounds. With platinum on carbon, hydrogen in water, Time= 0.5h, T= 175 °C , p= 60006Torr Hronec, Milan; Fulajtarova, Katarina; Micusik, Matej; Applied Catalysis A: General; vol. 468; (2013); p. 426 - 431 View in Reaxys Reaction Steps: 2 1: water / 239.84 °C / |Autoclave; |Inert atmosphere 2: hydrogen; palladium on activated charcoal / water / 1 h / 159.84 °C / 37503.8 Torr With palladium on activated charcoal, hydrogen in water Li, Guangyi; Li, Ning; Zheng, Mingyuan; Li, Shanshan; Wang, Aiqin; Cong, Yu; Wang, Xiaodong; Zhang, Tao; Green Chemistry; vol. 18; nb. 12; (2016); p. 3607 - 3613 View in Reaxys Reaction Steps: 2 1: MgAl-HT catalyst / water / 0.03 h / 229.84 °C / |Autoclave; |Inert atmosphere; |Green chemistry 2: hydrogen; palladium on activated charcoal / water / 1 h / 159.84 °C / 37503.8 Torr With palladium on activated charcoal, hydrogen in water Li, Guangyi; Li, Ning; Zheng, Mingyuan; Li, Shanshan; Wang, Aiqin; Cong, Yu; Wang, Xiaodong; Zhang, Tao; Green Chemistry; vol. 18; nb. 12; (2016); p. 3607 - 3613 View in Reaxys OH

O O

Rx-ID: 36689291 View in Reaxys 25/449 Yield 79 %

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View in Reaxys 9.7 mol

General procedure: Catalytic experiments were performed using procedure and analytical methods described in our previous paper [14]. For a typical reaction, 20 ml of water, 0.5–1.0 g of reactant and given amount of metal catalyst was added to the reactor vessel. After sealing the reactor was several times flushed with low pressure hydrogen and then pressurized with hydrogen usually to 30–80 bar (ambient temperature). The reactor was then heated to the desired temperature and the stirring speed adjusted to 1500 rpm to eliminate external mass-transfer effects. After an appropriate reaction timethe reactor was quickly cooled down, the reactor contents pour out to vial and the catalyst separated from the aqueous phase by centrifugation. The quantitative determination of the liquid products concentration was done using gas chromatography by the external standard method and using response factors of the corresponding standard compounds. A gas chromatograph–mass spectrometer combination was used to identify the organic compounds. With hydrogen in water, Time= 0.5h, T= 175 °C , p= 60006Torr Hronec, Milan; Fulajtarova, Katarina; Micusik, Matej; Applied Catalysis A: General; vol. 468; (2013); p. 426 - 431 View in Reaxys With 20 Ni/Co3O4, hydrogen in water, Time= 6h, T= 149.84 °C , p= 30003Torr , Autoclave, Reagent/catalyst, chemoselective reaction Li, Xing-Long; Deng, Jin; Shi, Jing; Pan, Tao; Yu; Xu, Hua-Jian; Fu, Yao; Green Chemistry; vol. 17; nb. 2; (2015); p. 1038 - 1046 View in Reaxys With hydrogen in water, Time= 4h, T= 140 °C , p= 30003Torr , Autoclave Yang, Yanliang; Ma, Jiping; Jia, Xiuquan; Du, Zhongtian; Duan, Ying; Xu, Jie; RSC Advances; vol. 6; nb. 56; (2016); p. 51221 - 51228 View in Reaxys OH

Rx-ID: 42219297 View in Reaxys 26/449 Yield

Conditions & References

59 %, 11 % With Au/ZrO2, hydrogen in water, Time= 1.2h, T= 160 °C , p= 30003Torr , Autoclave, Reagent/catalyst, Time Zhang, Gao-Shuo; Zhu, Ming-Ming; Zhang, Qi; Liu, Yong-Mei; He, He-Yong; Cao, Yong; Green Chemistry; vol. 18; nb. 7; (2016); p. 2155 - 2164 View in Reaxys O O

O OH

Rx-ID: 42219298 View in Reaxys 27/449 Yield

Conditions & References

41 %, 11 %, 42 %

With Au on mesoporous silica nanoparticles, hydrogen in water, Time= 1.2h, T= 160 °C , p= 30003Torr , Autoclave Zhang, Gao-Shuo; Zhu, Ming-Ming; Zhang, Qi; Liu, Yong-Mei; He, He-Yong; Cao, Yong; Green Chemistry; vol. 18; nb. 7; (2016); p. 2155 - 2164 View in Reaxys

O HO OH

Rx-ID: 42526322 View in Reaxys 28/449

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Yield

Conditions & References

97 %Spectr.

With dimethylsulfoxide-d6, MoO2Cl2(dimethylsulfoxide)2, Time= 0.666667h, T= 130 °C , Sealed tube, Microwave irradiation, Molecular sieve, Green chemistry, chemoselective reaction García, Nuria; Rubio-Presa, Rubén; García-García, Patricia; Fernández-Rodríguez, Manuel A.; Pedrosa, María R.; Arnáiz, Francisco J.; Sanz, Roberto; Green Chemistry; vol. 18; nb. 8; (2016); p. 2335 - 2340 View in Reaxys

O HO

O OH

Rx-ID: 43840628 View in Reaxys 29/449 Yield

Conditions & References Synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane from xylose Reactions were performed in a Parr Instruments (Parr Instruments,Moline, IL, USA) stirred reactor with a 300 ml glass liner.Typically, xylose and catalyst were loaded into the reactor with50 ml water, the systemwas charged with hydrogen and evacuatedfive times before being brought up to 15 bar hydrogen. The reactorwas then heated to 433 K and pressurized to the final hydrogenpressure and the reactor was stirred at 250 rpm until the reactionwas complete. Progress of the reaction was monitored by withdrawingsamples via a sampling tube and analyzing by HPLC forunreacted xylose. Upon completion of the reaction, typically after5 h, the catalyst was removed by filtration. The filtrate wasextracted with diethyl ether to remove HPO, CPO, and some of theTHFA. The aqueous portionwas then reduced in volume at reducedpressure to give a heavy residue. This residue was then extractedwith 90:10 hexane:ethyl acetate. Removal of this solvent mix atreduced pressure gave solid 1. 13C NMR (D2O, 125 MHz) d22.8, 33.1 64.6, 68.4,103.1. 1H NMR (D2O, 500 MHz): d1.74 (complex multiplet,2H), 1.84 (complex multiplet, 2H), 1.9 (complex multiplet, 2H), 1.97(complex multiplet, 2H), 3.48 (d, J 12.5, 2H), 3.95 (t, J 7, 2H, 4.05(d, J 12.5, 2H)). EIMS m/z, (relative intensity) 84, (100); 42 (21); 56(16); 43 (11).Isolation of the ringeclosed monomer (2) was accomplishedusing flash chromatography (CombiFlash Rf 200i, Teledyne Isco,Lincoln, NE, USA). Separations were performed using two stackedRedi-Sep Gold Silica columns (12 g each). The mobile phase was ahexane/ethyl acetate gradient flowing at 25 ml/min. The gradientused was a 1e10 column volume (CV) gradient to 10percent EtOAC, holdat 10percent EtOAc for 30 CV, then up to 100percent EtOAc in 10 CV, hold for10 CV, then 0percent EtOAc for 5 CV. Detectionwas accomplished using anelectrospray detector held at 313 K.2-hydroxy-2-hydroxymethyltetrahydrofuran, 2. 13C NMR(acetone-d6, 125 MHz): d 23.2, 33.6, 64.7, 67.1, 102.4. 1H NMR(acetone-d6, 500 MHz): d1.61 (complex multiplet, 2H), 1.78 (complexmultiplet, 2H), 1.85 (complex multiplet, 2H), 1.97 (complexmultiplet, 2H), 2.77 (t, J 0.8, 1H), 2.81 (s, 1H), 3.36 (d, J H), 3.88(m, J 6.0, 2H), 4.01(d, J 11.5, 2H). EIMS m/z, (relative intensity)101, (100); 59, (88); 43, (28); 41, (28). With hydrogen in water, Time= 5.5h, T= 159.84 °C , p= 11251.1Torr Jackson, Michael A.; Blackburn, Judith A.; Price, Neil P.J.; Vermillion, Karl E.; Peterson, Steven C.; Ferrence, Gregory M.; Carbohydrate Research; vol. 432; (2016); p. 9 - 16 View in Reaxys

O H

O OH

O O

HO O

Rx-ID: 43840629 View in Reaxys 30/449 Yield

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ane:ethyl acetate. Removal of this solvent mix atreduced pressure gave solid 1. 13C NMR (D2O, 125 MHz) d22.8, 33.1 64.6, 68.4,103.1. 1H NMR (D2O, 500 MHz): d1.74 (complex multiplet,2H), 1.84 (complex multiplet, 2H), 1.9 (complex multiplet, 2H), 1.97(complex multiplet, 2H), 3.48 (d, J 12.5, 2H), 3.95 (t, J 7, 2H, 4.05(d, J 12.5, 2H)). EIMS m/z, (relative intensity) 84, (100); 42 (21); 56(16); 43 (11).Isolation of the ringeclosed monomer (2) was accomplishedusing flash chromatography (CombiFlash Rf 200i, Teledyne Isco,Lincoln, NE, USA). Separations were performed using two stackedRedi-Sep Gold Silica columns (12 g each). The mobile phase was ahexane/ethyl acetate gradient flowing at 25 ml/min. The gradientused was a 1e10 column volume (CV) gradient to 10percent EtOAC, holdat 10percent EtOAc for 30 CV, then up to 100percent EtOAc in 10 CV, hold for10 CV, then 0percent EtOAc for 5 CV. Detectionwas accomplished using anelectrospray detector held at 313 K.2-hydroxy-2-hydroxymethyltetrahydrofuran, 2. 13C NMR(acetone-d6, 125 MHz): d 23.2, 33.6, 64.7, 67.1, 102.4. 1H NMR(acetone-d6, 500 MHz): d1.61 (complex multiplet, 2H), 1.78 (complexmultiplet, 2H), 1.85 (complex multiplet, 2H), 1.97 (complexmultiplet, 2H), 2.77 (t, J 0.8, 1H), 2.81 (s, 1H), 3.36 (d, J H), 3.88(m, J 6.0, 2H), 4.01(d, J 11.5, 2H). EIMS m/z, (relative intensity)101, (100); 59, (88); 43, (28); 41, (28). With hydrogen in water, Time= 5.5h, T= 159.84 °C , p= 11251.1Torr Jackson, Michael A.; Blackburn, Judith A.; Price, Neil P.J.; Vermillion, Karl E.; Peterson, Steven C.; Ferrence, Gregory M.; Carbohydrate Research; vol. 432; (2016); p. 9 - 16 View in Reaxys

O H

O OH

O O

HO O

Rx-ID: 43840631 View in Reaxys 31/449 Yield

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O OH

Rx-ID: 44156040 View in Reaxys 32/449 Yield

Conditions & References

27 %Chro- With copper-nickel on zirconium oxide bimetallic catalysts in isopropyl alcohol, Time= 4h, T= 220 °C , Inert atmosmat., 33.8 phere, Sealed tube %Chromat. Chang, Xin; Liu, An-Feng; Cai, Bo; Luo, Jin-Yue; Pan, Hui; Huang, Yao-Bing; ChemSusChem; vol. 9; nb. 23; (2016); p. 3330 - 3337 View in Reaxys

O O

Rx-ID: 44156041 View in Reaxys 33/449 Yield

Conditions & References

33.5 With palladium on zirconium oxide bimetallic catalysts in isopropyl alcohol, Time= 4h, T= 220 °C , Inert atmosphere, %Chromat. Sealed tube Chang, Xin; Liu, An-Feng; Cai, Bo; Luo, Jin-Yue; Pan, Hui; Huang, Yao-Bing; ChemSusChem; vol. 9; nb. 23; (2016); p. 3330 - 3337 View in Reaxys NH 2

Rx-ID: 747130 View in Reaxys 34/449 Yield 75 %

Conditions & References With oxygen, potassium iodide, sodium nitrite in water, acetonitrile, Time= 8h, Reflux Chaudhari, Hemchandra K.; Telvekar, Vikas N.; Synthetic Communications; vol. 43; nb. 8; (2013); p. 1155 - 1160 View in Reaxys

18 %

With potassium hydroxide in ethyl acetate, T= -78 °C , Product distribution Hoffman, Robert V.; Kumar, Anil; Journal of Organic Chemistry; vol. 49; nb. 21; (1984); p. 4011 - 4014 View in Reaxys With water, oxygen, copper, Reagens 4: OsO4 Demjanow; Schuikina; Zhurnal Obshchei Khimii; vol. 6; (1936); p. 350; Chem. Zentralbl.; vol. 107; nb. II; (1936); p. 1905 View in Reaxys With pyridine-4-carbaldehyde, hydrogenchloride, sodium hydroxide, 1.) CH3OH, reflux, 7 h, Yield given. Multistep reaction Ohta, Shunsaku; Okamoto, Masao; Synthesis; nb. 9; (1982); p. 756 - 758 View in Reaxys

42 % Chromat.

With 2,6-dimethylpyridine, TEMPOL, water, lithium perchlorate in acetonitrile, T= 23 °C , electrolysis, a platinum gauze electrode, +0.33 V (vs. Ag/Ag(1+)) Semmelhack, M. F.; Schmid, Christopher R.; Journal of the American Chemical Society; vol. 105; nb. 22; (1983); p. 6732 - 6734 View in Reaxys With water in dimethyl sulfoxide, Time= 18h, T= 30 °C , pH= 7, aq. phosphate buffer, Enzymatic reaction Leisch, Hannes; Grosse, Stephan; Iwaki, Hiroaki; Hasegawa, Yoshie; Lau, Peter C.K.; Canadian Journal of Chemistry; vol. 90; nb. 1; (2012); p. 39 - 45

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View in Reaxys With dipotassium peroxodisulfate, tris(bipyridine)ruthenium(II) dichloride hexahydrate, water in acetonitrile, Time= 12h, T= 20 °C , Sealed tube, Irradiation, Green chemistry Iqbal, Naeem; Cho, Eun Jin; Advanced Synthesis and Catalysis; vol. 357; nb. 10; (2015); p. 2187 - 2192 View in Reaxys O

Rx-ID: 1792691 View in Reaxys 35/449 Yield

Conditions & References With diisobutylaluminium hydride in tetrahydrofuran, hexane, Time= 3h, T= -78 °C , Yield given. Yields of byproduct given Kim, Sunggak; Ahn, Kyo Han; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1717 - 1724 View in Reaxys

63 % Chromat., 34 % Chromat., 2 % Chromat.

With lithium aluminium tetrahydride, cerium(III) chloride in tetrahydrofuran, Time= 0.166667h, Ambient temperature

63 % Chromat., 2 % Chromat., 34 % Chromat.

With lithium aluminium tetrahydride, cerium(III) chloride, Time= 0.166667h, Ambient temperature, Without catalyst, Product distribution

6 % Chromat., 4 % Chromat., 88 % Chromat.

With sodium tetrahydroborate, copper(l) chloride in methanol, Time= 0.0833333h, other metallic salts, Product distribution

Fukuzawa, Shin-ichi; Fujinami, Tatsuo; Yamauchi, Shoji; Sakai, Shizuyoshi; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 1929 - 1932 View in Reaxys

Gemal, Andre L.; Luche, Jean-Louis; Journal of the American Chemical Society; vol. 103; nb. 18; (1981); p. 5454 - 5459 View in Reaxys With hydrogen, Ru(CO)2(OAc)2(PnBu3)(PPh3) in toluene, Time= 3h, T= 60 °C , p= 18751.9Torr Micoli, Francesca; Oberhauser, Werner; Salvini, Antonella; Bianchini, Claudio; Journal of Organometallic Chemistry; vol. 692; nb. 11; (2007); p. 2334 - 2341 View in Reaxys

6 %Chromat.

1 With sodium tetrahydroborate, cerium(III) chloride heptahydrate in 2-methyltetrahydrofuran, Time= 0.0333333h, Solvent, Reagent/catalyst, Overall yield = 100 percentChromat. Nardi, Monica; Sindona, Giovanni; Costanzo, Paola; Oliverio, Manuela; Procopio, Antonio; Tetrahedron; vol. 71; nb. 7; (2015); p. 1132 - 1135 View in Reaxys

20 %Chromat.

1 With sodium tetrahydroborate, cerium triflate in ethanol, Time= 0.0333333h, Solvent, Reagent/catalyst, Overall yield = 100 percentChromat. Nardi, Monica; Sindona, Giovanni; Costanzo, Paola; Oliverio, Manuela; Procopio, Antonio; Tetrahedron; vol. 71; nb. 7; (2015); p. 1132 - 1135 View in Reaxys

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HO H 2N

O O

Rx-ID: 35626972 View in Reaxys 36/449 Yield

Conditions & References

31 %

2.2 Determination of products General procedure: Reactivity assays were performed as follows: the respective amino acid (ACCH, ACBH, ACPH, ACHH, AIBH) was dissolved in 10mL of DMF/H2O mixture (3/1 V/V) in a 20 mL sealable tube. With MeCN (10μL) as inner standard, NH4OH and the catalyst were then added to the mixture. Hydrogen peroxide was added through the septum with a syringe and the evolved ethylene, cyclobutanone, cyclopentanone, cyclohexanone or acetone was measured by removing 0.25 mL from the headspace with a gastight syringe and the sample was injected into a gas chromatograph. The concentration of the corresponding product in the headspace is linearly proportional to the concentration of the product in the reaction mixture. GC analyses were performed on a Hewlett Packard 5890 gas chromatograph equipped with a flame ionization detector and a 30m Supelcowax column. With ammonium hydroxide, C18H12N5 (1-)*Fe(3+)*2Cl(1-), dihydrogen peroxide in water, N,N-dimethyl-formamide, Time= 0.75h, T= 35 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Kinetics, Time Lakk-Bogth, Dra; Harasztia, Mikls; Csonka, Rbert; Speier, Gbor; Kaizer, Jzsef; Polyhedron; vol. 89; (2015); p. 91 - 95 View in Reaxys

22 %

With ammonium hydroxide, [CuII(2,2'-bipyridine)(1-aminocyclopentane-1-carboxylic acid(H-))]ClO4*H2O, dihydrogen peroxide in water, N,N-dimethyl-formamide, T= 35 °C , Kinetics Pap, József S.; El Bakkali-Tahéri, Nadia; Fadel, Antoine; Góger, Szabina; Bogáth, Dóra; Molnár, Milán; Giorgi, Michel; Speier, Gábor; Simaan, A. Jalila; Kaizer, József; European Journal of Inorganic Chemistry; vol. 2014; nb. 17; (2014); p. 2829 - 2838 View in Reaxys With [1,6-bis(2-hydroxyphenyl)-2,5-diaza-hexa-1,5-diene]iron(III) chloride, dihydrogen peroxide in water, N,N-dimethyl-formamide, T= 35 °C , Catalytic behavior, Kinetics Goger, Szabina; Bogath, Dora; Barath, Gabor; Simaan, A. Jalila; Speier, Gabor; Kaizer, Jozsef; Journal of Inorganic Biochemistry; vol. 123; (2013); p. 46 - 52 View in Reaxys 2.8 Determination of products and kinetic measurements General procedure: Kinetic studies on the catalytic oxidation of amino acids by CuCl2 or Cu(AA)2 complexes were performed in a 3:1 DMF–water mixture at 35°C. Assays were performed as follows: respective amino acid (3.6×10− 4mol) was dissolved in 10mL of the solvent mixture in a sealable tube of 20mL. To the mixture were then added MeCN (10μL) as internal standard, the catalyst (7.2×10− 8mol) and NH4OH (3.6×10− 4mol). Hydrogen peroxide (32μL, 3.6×10− 4mol) was then added through the septum with a syringe and the evolved product(s) were measured by removing 250μL of the headspace by GC analysis. The concentration of products in the head space are linearly proportional to the concentration of those in the reaction mixture. With ammonium hydroxide, dihydrogen peroxide, copper dichloride in water, N,N-dimethyl-formamide, T= 35 °C , Kinetics, Catalytic behavior, Reagent/catalyst Goger, Szabina; Pap, Jozsef S.; Bogath, Dora; Simaan, A. Jalila; Speier, Gabor; Giorgi, Michel; Kaizer, Jozsef; Polyhedron; vol. 73; (2014); p. 37 - 44 View in Reaxys OH

O OH

Rx-ID: 36338234 View in Reaxys 37/449 Yield

Conditions & References With water, hydrogen, Time= 4h, T= 160 °C , p= 30003Torr , Autoclave

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Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys With methanol, acetic acid in water, Time= 4h, T= 180 °C , p= 7500.75Torr , Inert atmosphere Xu, Ying; Qiu, Songbai; Long, Jinxing; Wang, Chenguang; Chang, Jiamin; Tan, Jin; Liu, Qiying; Ma, Longlong; Wang, Tiejun; Zhang, Qi; RSC Advances; vol. 5; nb. 111; (2015); p. 91190 - 91195 View in Reaxys O

Rx-ID: 40391967 View in Reaxys 38/449 Yield

Conditions & References With palladium on activated charcoal, hydrogen in water, Time= 2h, T= 275 °C , p= 48004.8Torr Shafaghat, Hoda; Sirous Rezaei, Pouya; Daud, Wan Mohd Ashri Wan; RSC Advances; vol. 5; nb. 43; (2015); p. 33990 - 33998 View in Reaxys O

O HO

Rx-ID: 40391968 View in Reaxys 39/449 Yield

Conditions & References With hydrogen in water, Time= 2h, T= 275 °C , p= 48004.8Torr Shafaghat, Hoda; Sirous Rezaei, Pouya; Daud, Wan Mohd Ashri Wan; RSC Advances; vol. 5; nb. 43; (2015); p. 33990 - 33998 View in Reaxys

O O

Rx-ID: 40657700 View in Reaxys 40/449 Yield

Conditions & References Experimental set up and reaction procedure General procedure: Furfural hydrogenation reactions were performed in a 50 ml stainless steel reactor connected with a flexible metal capillary toa hydrogen supply system recording at constant pressure the con-sumption of hydrogen in defined reaction times. The reactor wasloaded with the liquid reaction mixture (usually 5 ml) and the cat-alyst. The air was purged out from the reactor by flushing withnitrogen and then four times with hydrogen. The reactor pres-surized to the desired pressure with hydrogen was placed intothermostatic oil bath, and after 5–7 min of heating, the reactantswere mixed by shaking the reactor using a vibrator. This momentwas the start of reaction. A constant hydrogen pressure was main-tained throughout the reaction. The vigorous agitation ensured thatthe measured rate of hydrogen consumption was not influencedby mass-transfer effects. Hydrogenation was stopped when during3–5 min hydrogen consumption was practically zero. The samples were analyzed using a gas chromatography (Shimadzu GC-17A)equipped with flame ionization detector by the formerly describedCuOprocedure [2]. The qualitative determination of products was doneby the external standard method using aqueous solutions of eachproduct with known concentration and response factors. Perfor-mance of catalysts was evaluated in terms of (percent) conversion offurfural and (percent) selectivity to furfuryl alcohol calculated on theamount of converted furfural With 5-palladium/activated carbon, hydrogen in water, Time= 1.66667h, T= 40 - 130 °C , p= 6000.6Torr , Reagent/ catalyst Fulajtárova, Katarína; Soták, Tomáš; Hronec, Milan; Vávra, Ivo; Dobročka, Edmund; Omastová, Mária; Applied Catalysis A: General; vol. 502; (2015); p. 78 - 85 View in Reaxys

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Rx-ID: 40922082 View in Reaxys 41/449 Yield

Conditions & References With methanol, water in aq. phosphate buffer, T= 28 °C , pH= 6.2, Enzymatic reaction, Michael Addition, enantioselective reaction Chen, Bi-Shuang; Resch, Verena; Otten, Linda G.; Hanefeld, Ulf; Chemistry - A European Journal; vol. 21; nb. 7; (2015); p. 3020 - 3030 View in Reaxys OH

O OH

Rx-ID: 41216262 View in Reaxys 42/449 Yield

Conditions & References With methanol, acetic acid in water, Time= 4h, T= 180 °C , p= 7500.75Torr , Inert atmosphere, Autoclave, Catalytic behavior, Reagent/catalyst Xu, Ying; Qiu, Songbai; Long, Jinxing; Wang, Chenguang; Chang, Jiamin; Tan, Jin; Liu, Qiying; Ma, Longlong; Wang, Tiejun; Zhang, Qi; RSC Advances; vol. 5; nb. 111; (2015); p. 91190 - 91195 View in Reaxys

N N

Rx-ID: 41674726 View in Reaxys 43/449 Yield

Conditions & References in benzene-d6, Equilibrium constant, Solvent Castro-Alvarez, Alejandro; Carneros, Héctor; Sánchez, Dani; Vilarrasa, Jaume; Journal of Organic Chemistry; vol. 80; nb. 24; (2015); p. 11977 - 11985 View in Reaxys

Rx-ID: 1515146 View in Reaxys 44/449 Yield 90 %

Conditions & References With formaldehyd, silica gel, iron(III) chloride, Time= 0.0833333h, T= 20 °C Fadel, Antoine; Yefsah, Ramdane; Salauen, Jacques; Synthesis; nb. 1; (1987); p. 37 - 40 View in Reaxys

83 %

3 General procedure: A stirred solution of the acetal (2, 3.5 mmol) in dry hexane (5 ml), under dry nitrogen at 25 C, was treated with 1 (1.7 g, 10.6 mmol). The mixture was stirred for 2 h, treated with water, and extracted with dichloromethane (10 ml). The extracts were washed with brine solution, dried (Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography on neutral alumina(50–325 mesh, eluent: 2.5:97.5 ethyl acetate–hexane), to obtain the corresponding carbonyl compound (3). The purity was estimated to be >98percent by 1H and 13C NMRspectroscopic analysis. In the case of solid acetals, 0.5 ml of dichloromethane along with hexane was added for added solubility; in the case of thioacetals, 21.2 mmol of 1 was used fo reffective deprotection With chloral hydrate in hexane, Time= 0.5h, T= 25 °C , Inert atmosphere, Solvent, Temperature Chandrasekhar, Sosale; Shrinidhi, Annadka; Synthetic Communications; vol. 44; nb. 13; (2014); p. 1904 - 1913

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View in Reaxys 82 %

With boron trifluoride diethyl etherate, sodium iodide in acetonitrile, Time= 2h, Heating Mandal, Arun K.; Shrotri, P. Y.; Ghogare, A. D.; Synthesis; nb. 3; (1986); p. 221 - 222 View in Reaxys

98 % Chromat.

With water, β-cyclodextrin, Time= 16h, T= 20 °C Ji, Hong-Bing; European Journal of Organic Chemistry; nb. 18; (2003); p. 3659 - 3662 View in Reaxys O HO

OH O

Rx-ID: 4516363 View in Reaxys 45/449 Yield

Conditions & References

8 %, 50 %

With ozone in neat (no solvent), Time= 10h, T= 20 °C , UV-irradiation Hwang, Kuo Chu; Sagadevan, Arunachalam; Science; vol. 346; nb. 6216; (2014); p. 1495 - 1498 View in Reaxys With 2-hydroxy-1,3-isoindolinedione, sulfuric acid, oxygen, cobalt(II) 2,4-pentanedionate, 1.) CH3COOH, 100 deg C, 6 h, 2.) CH3OH, 65 deg C, 15 h, Yield given. Multistep reaction. Yields of byproduct given Ishii, Yasutaka; Iwahama, Takahiro; Sakaguchi, Satoshi; Nakayama, Kouichi; Nishiyama, Yutaka; Journal of Organic Chemistry; vol. 61; nb. 14; (1996); p. 4520 - 4526 View in Reaxys

NH 2

H NH 2

O O

Rx-ID: 37304918 View in Reaxys 46/449 Yield

Conditions & References 2.7. Substrate specificity and enantioselectivity General procedure: Amino donor specificity was assayed by following the similar procedure of Section 2.5. The amino donor substrates (10 mM) listed in Table 1 reacted with pyruvate (10 mM) as amino acceptor. For racemic amino donor, the concentration was 20 mM. After the reaction, residual pyruvate was analyzed by HPLC according to Section 2.10. Amino acceptor specificity was assayed by following the similar procedure of Section 2.5. The amino acceptor substrates (10 mM) listed in Table 2 reacted with (S)-α-MBA (10 mM) as amino donor. After the reaction, the amount of produced acetophenone was analyzed and the ee values of the produced amines were determined according to Section 2.10. With pyridoxal 5'-phosphate, recombinant ω-transaminase from Burkholderia vietnamiensis G4 in aq. phosphate buffer, Time= 0.0833333h, T= 37 °C , pH= 7.4, Enzymatic reaction, enantioselective reaction Jiang, Jinju; Chen, Xi; Feng, Jinhui; Wu, Qiaqing; Zhu, Dunming; Journal of Molecular Catalysis B: Enzymatic; vol. 100; (2014); p. 32 - 39 View in Reaxys

OH O

Rx-ID: 37472277 View in Reaxys 47/449 Yield

Conditions & References With tert.-butylhydroperoxide in neat (no solvent), Time= 24h, T= 26 °C Alshammari, Hamed; Miedziak, Peter J.; Davies, Thomas E.; Willock, David J.; Knight, David W.; Hutchings, Graham J.; Catalysis Science and Technology; vol. 4; nb. 4; (2014); p. 908 - 911 View in Reaxys

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N N

O– NH 2 Cu 2+

O –O

H 2O

Rx-ID: 38157687 View in Reaxys 48/449 Yield

Conditions & References With ammonium hydroxide, dihydrogen peroxide in water, N,N-dimethyl-formamide, T= 35 °C , Kinetics, Solvent Pap, Jõzsef S.; El Bakkali-Tahéri, Nadia; Fadel, Antoine; Gõger, Szabina; Bogáth, Dõra; Molnár, Milán; Giorgi, Michel; Speier, Gábor; Simaan, A. Jalila; Kaizer, Jõzsef; European Journal of Inorganic Chemistry; nb. 17; (2014); p. 2829 - 2838 View in Reaxys

NH 2

Rx-ID: 35100302 View in Reaxys 49/449 Yield

Conditions & References

10 %Chro- With (S)-α-alanine, pyridoxal 5'-phosphate, NAD, ammonium formate, alcohol dehydrogenase, lactate dehydrogenmat., 85 ase in aq. phosphate buffer, Time= 24h, T= 30 °C , pH= 7.5, Enzymatic reaction, Reagent/catalyst %Chromat. Tauber, Katharina; Fuchs, Michael; Sattler, Johann H.; Pitzer, Julia; Pressnitz, Desiree; Koszelewski, Dominik; Faber, Kurt; Pfeffer, Jan; Haas, Thomas; Kroutil, Wolfgang; Chemistry - A European Journal; vol. 19; nb. 12; (2013); p. 4030 - 4035 View in Reaxys

S O

Rx-ID: 35599735 View in Reaxys 50/449 Yield

Conditions & References

75 %Spectr., 92 %Spectr.

4.4 General procedure for photodeprotection reaction General procedure: Irradiation reactions were carried out using an ultra-high pressure mercury lamp (SX–UI–500H, USHIO) as a light source. A CH3CN (1.0 vol percent H2O, 1.0×10−2 M) solution of acetal 7 in an NMR tube was irradiated through Pyrex filter until 7 was totally consumed. The field was determined by 1H NMR spectroscopy using 1,3,5-trioxane as an internal standard. in acetonitrile-D3, water-d2, Time= 2.66667h, T= 20 °C , Irradiation Sugiura, Ryo; Kozaki, Rikio; Kitani, Satoru; Gosho, Yoshinori; Tanimoto, Hiroki; Nishiyama, Yasuhiro; Morimoto, Tsumoru; Kakiuchi, Kiyomi; Tetrahedron; vol. 69; nb. 19; (2013); p. 3984 - 3990 View in Reaxys

S O

18OH

S O

O OH

Rx-ID: 35599736 View in Reaxys 51/449 Yield

Conditions & References 4.5 18O labeling experiment General procedure: As a control, a 1.0×10−2 M solution of 7d or 7j in CH3CN/H2O (99/1 v/v) was irradiated at >280 nm from an ultra-high pressure mercury lamp until 7d or 7j was totally consumed. For experiment of 7d, the

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reaction solution was directly analyzed by MS (CI). For experiment of 7j, aldehyde 6j, and PLPG 1d were isolated from the reaction solution and then analyzed by MS (CI), respectively. Next, a 1.0×10−2 M solution of 7d or 7j in CH3CN/H218O (99/1 v/v) was irradiated. Analysis of each resulting reaction solution was done as above. The values of label incorporation into the products were calculated from the comparison of the height of [M+H]+ peak and [M +2+H]+ peak of each labeled and unlabeled products. With H2 18O in acetonitrile, T= 20 °C , Irradiation Sugiura, Ryo; Kozaki, Rikio; Kitani, Satoru; Gosho, Yoshinori; Tanimoto, Hiroki; Nishiyama, Yasuhiro; Morimoto, Tsumoru; Kakiuchi, Kiyomi; Tetrahedron; vol. 69; nb. 19; (2013); p. 3984 - 3990 View in Reaxys NH 2

Rx-ID: 35675784 View in Reaxys 52/449 Yield

Conditions & References

55 %, 45 %

With carbonylchloro[4,5-bis(diisopropylphosphinomethyl)acridine]hydridoruthenium(II), water in 1,4-dioxane, Time= 48h, T= 135 °C , Schlenk technique, Inert atmosphere, Pressure Khusnutdinova, Julia R.; Ben-David, Yehoshoa; Milstein, David; Angewandte Chemie - International Edition; vol. 52; nb. 24; (2013); p. 6269 - 6272; Angew. Chem.; vol. 125; nb. 24; (2013); p. 6389 - 6392,4 View in Reaxys

H –O(v4)

(v2)

(v6)

(v4)

N N

Ru 2+ – P H

(v4)

N (v1)

– + (v5) N Ru P (v3) (v4) (v4)

(v3)

Rx-ID: 35936659 View in Reaxys 53/449 Yield

Conditions & References in benzene-d6, Time= 2h, T= 25 °C , Inert atmosphere, Glovebox Huff, Chelsea A.; Kampf, Jeff W.; Sanford, Melanie S.; Chemical Communications; vol. 49; nb. 64; (2013); p. 7147 - 7149 View in Reaxys

Rx-ID: 36338226 View in Reaxys 54/449 Yield

Conditions & References With water, hydrogen, Time= 4h, T= 160 °C , p= 30003Torr , Autoclave Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys Reaction Steps: 2 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / |Autoclave 2: hydrogen; water / 4 h / 160 °C / 30003 Torr / pH 7 / |Autoclave With water, hydrogen, sodium carbonate Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys General procedure: Catalytic experiments were performed using procedure and analytical methods described in our previous paper [14]. For a typical reaction, 20 ml of water, 0.5–1.0 g of reactant and given amount of metal catalyst was added to the reactor vessel. After sealing the reactor was several times flushed with low pressure hydrogen and

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then pressurized with hydrogen usually to 30–80 bar (ambient temperature). The reactor was then heated to the desired temperature and the stirring speed adjusted to 1500 rpm to eliminate external mass-transfer effects. After an appropriate reaction timethe reactor was quickly cooled down, the reactor contents pour out to vial and the catalyst separated from the aqueous phase by centrifugation. The quantitative determination of the liquid products concentration was done using gas chromatography by the external standard method and using response factors of the corresponding standard compounds. A gas chromatograph–mass spectrometer combination was used to identify the organic compounds. With 5 palladium on charcoal, hydrogen in water, Time= 1h, T= 160 °C , p= 22502.3Torr Hronec, Milan; Fulajtarova, Katarina; Micusik, Matej; Applied Catalysis A: General; vol. 468; (2013); p. 426 - 431 View in Reaxys O O OH

Rx-ID: 36338231 View in Reaxys 55/449 Yield

Conditions & References With 5-hydroxymethylfuran-2-carboxaldehyde, water, hydrogen, Time= 4h, T= 160 °C , p= 30003Torr , Autoclave Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys O

O OH

Rx-ID: 36338237 View in Reaxys 56/449 Yield

Conditions & References With water, hydrogen, Time= 4h, T= 160 °C , p= 30003Torr , pH= 7, Autoclave, Reagent/catalyst, pH-value Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie; Green Chemistry; vol. 15; nb. 7; (2013); p. 1932 - 1940 View in Reaxys

racemate

Rx-ID: 36457377 View in Reaxys 57/449 Yield

Conditions & References With 1,4-dioxane, T= 140 °C , Sealed tube, High pressure, Kinetics, Mechanism, Temperature Nesprias, Rosa; Eyler, Gladys; Canizo, Adriana; Australian Journal of Chemistry; vol. 66; nb. 9; (2013); p. 1080 1087 View in Reaxys

O F O

F racemate

Rx-ID: 36457379 View in Reaxys 58/449

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Yield

Rx-ID: 36689292 View in Reaxys 59/449 Yield

Conditions & References General procedure: Catalytic experiments were performed using procedure and analytical methods described in our previous paper [14]. For a typical reaction, 20 ml of water, 0.5–1.0 g of reactant and given amount of metal catalyst was added to the reactor vessel. After sealing the reactor was several times flushed with low pressure hydrogen and then pressurized with hydrogen usually to 30–80 bar (ambient temperature). The reactor was then heated to the desired temperature and the stirring speed adjusted to 1500 rpm to eliminate external mass-transfer effects. After an appropriate reaction timethe reactor was quickly cooled down, the reactor contents pour out to vial and the catalyst separated from the aqueous phase by centrifugation. The quantitative determination of the liquid products concentration was done using gas chromatography by the external standard method and using response factors of the corresponding standard compounds. A gas chromatograph–mass spectrometer combination was used to identify the organic compounds. With platinum on carbon, hydrogen in water, Time= 0.5h, T= 175 °C , p= 60006Torr Hronec, Milan; Fulajtarova, Katarina; Micusik, Matej; Applied Catalysis A: General; vol. 468; (2013); p. 426 - 431 View in Reaxys

N N O O

Rx-ID: 36926888 View in Reaxys 60/449 Yield

Conditions & References With air, Time= 168h, T= 25 °C , Overall yield = > 90 percent Kise, Naoki; Kawano, Yusuke; Sakurai, Toshihiko; Journal of Organic Chemistry; vol. 78; nb. 24; (2013); p. 12453 - 12459 View in Reaxys OH

Rx-ID: 36977918 View in Reaxys 61/449 Yield

Conditions & References With tert.-butylhydroperoxide, Time= 24h, T= 26 °C , p= 760.051Torr , Reagent/catalyst Alshammari, Hamed; Miedziak, Peter J.; Knight, David W.; Willock, David J.; Hutchings, Graham J.; Catalysis Science and Technology; vol. 3; nb. 12; (2013); p. 3372 - 3373 View in Reaxys

Rx-ID: 9068748 View in Reaxys 62/449

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Yield

Conditions & References With hydrogen, dichlorobis(tricyclohexylphosphine)(benzylidene)rhodium in 1,2-dichloro-ethane, T= 70 °C , p= 760.051Torr Louie; Bielawski; Grubbs; Journal of the American Chemical Society; vol. 123; nb. 45; (2001); p. 11312 - 11313 View in Reaxys With hydrogen, T= 70 °C , p= 5171.62Torr Trost, Barry M.; Thaisrivongs, David A.; Hansmann, Max M.; Angewandte Chemie - International Edition; vol. 51; nb. 46; (2012); p. 11522 - 11526 View in Reaxys

O O

H N

Rx-ID: 32605769 View in Reaxys 63/449 Yield

Conditions & References in dimethylsulfoxide-d6, T= 25 °C , Equilibrium constant 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 O O

Rx-ID: 32769640 View in Reaxys 64/449 Yield

Conditions & References

39 %, 16 %

With dihydrogen peroxide in acetonitrile, Time= 9h, T= 65 - 68 °C Sen, Rupam; Saha, Debraj; Koner, Subratanath; Catalysis Letters; vol. 142; nb. 1; (2012); p. 124 - 130 View in Reaxys

14 %, 5 %

With sodium hypochlorite in acetonitrile, Time= 9h, T= 65 - 68 °C Sen, Rupam; Saha, Debraj; Koner, Subratanath; Catalysis Letters; vol. 142; nb. 1; (2012); p. 124 - 130 View in Reaxys O

O OH

Rx-ID: 33359681 View in Reaxys 65/449 Yield

Conditions & References

38.89 %, 35.59 %, 10.31 %

With 5 Pd(II)/C(eggshell), hydrogen in water, Time= 0.5h, T= 175 °C , p= 60006Torr Hronec, Milan; Fulajtarova, Katarina; Catalysis Communications; vol. 24; (2012); p. 100 - 104 View in Reaxys

O O

Rx-ID: 33359682 View in Reaxys 66/449

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Yield 17.46 %, 40.01 %, 23.4 %, 6.55 %

Conditions & References With hydrogen in water, Time= 0.5h, T= 160 °C , p= 60006Torr Hronec, Milan; Fulajtarova, Katarina; Catalysis Communications; vol. 24; (2012); p. 100 - 104 View in Reaxys

O HO

OH O

Rx-ID: 33564683 View in Reaxys 67/449 Yield

Conditions & References 9 :[Example 9] Production of ε-caprolactone from the adipic acid through the hydrogenation reaction [catalyst: CuO(80)SiO2 (20)]The catalyst was produced by using the same method as Example 1. The reaction temperature was fixed to 265°C, the reaction was performed by using the same method as Example 1, and the reaction results over time are described in the following Table 7. The present catalyst exhibited high selectivity of 86.5percent of εcaprolactone. With hydrogen in 1,4-dioxane, T= 265 °C , p= 18751.9Torr , Product distribution / selectivity Patent; Korea Research Institute Of Chemical Technology; EP2476674; (2012); (A2) English View in Reaxys O

O HO

OH O

Rx-ID: 33564684 View in Reaxys 68/449 Yield

Conditions & References 12 :[Example 12] Production of ε-caprolactone from the adipic acid through the hydrogenation reaction [catalyst: CuO(80)SiO2(20)]The catalyst was produced by using the same method as Example 1. The adipic acid was used instead of the levulinic acid as the reactant, the temperature and the pressure of the reactor were fixed to 265°C and 25 bar, respectively, and the reaction was performed by using the same method as Example 1. The results are described in the following Table 11.As confirmed through Table 11, the conversion of adipic acid was 100percent, and the catalyst exhibited very high selectivity of 80percent or more to ε-caprolactone. With hydrogen in 1,4-dioxane, Time= 30h, T= 265 °C , p= 18751.9Torr Patent; Korea Research Institute Of Chemical Technology; EP2476674; (2012); (A2) English View in Reaxys

O HO

OH O

Rx-ID: 33679462 View in Reaxys 69/449 Yield

Conditions & References 9 :The catalyst was produced by using the same method as Example 1. The reaction temperature was fixed to 265° C., the reaction was performed by using the same method as Example 1, and the reaction results over time are described in the following Table 7. The present catalyst exhibited high selectivity of 86.5percent of ε-caprolactone. With hydrogen, CuO(80)SiO2 (20) in 1,4-dioxane, Time= 8h, T= 265 °C , p= 18751.9Torr , Inert atmosphere, Product distribution / selectivity Patent; Korea Research Institute of Chemical Technology; US2012/197029; (2012); (A1) English View in Reaxys O

O OH

O HO

OH O

Rx-ID: 33679464 View in Reaxys 70/449

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Yield

Conditions & References 12 :The catalyst was produced by using the same method as Example 1. The adipic acid was used instead of the levulinic acid as the reactant, the temperature and the pressure of the reactor were fixed to 265° C. and 25 bar, respectively, and the reaction was performed by using the same method as Example 1. The results are described in the following Table 11. With hydrogen, CuO(80)SiO2 (20) in 1,4-dioxane, Time= 30h, T= 265 °C , p= 18751.9Torr , Inert atmosphere, Product distribution / selectivity Patent; Korea Research Institute of Chemical Technology; US2012/197029; (2012); (A1) English View in Reaxys

O O

Rx-ID: 33995983 View in Reaxys 71/449 Yield 62%

Conditions & References 2 : Synthesis of Compound (M-2) 22.0 g of the compound shown by the following formula (M-2) (compound (M-2)) was obtained in the same manner as in Example 1, except that 18.9 g (150 mmol) of cyclooctanone was used instead of 12.6 g of cyclopentanone (yield: 62percent). The 1H-NMR data for the compound (M-2) is shown below. 1H-NMR (CDCl ) δ: 1.38-2.03 (m, 23H, CH , CH ), 2.46 (br, 1H, OH), 3.38 (t, 2H, CH ), 5.36 (s, 1H, CH), 5.96 (s, 1H, 3 2 3 2 CH). Patent; JSR Corporation; US2012/258402; (2012); (A1) English View in Reaxys

60%

8 : Example 8 Example 8 42.2 g of the compound shown by the following formula (M-8) (compound (M-8)) was obtained in the same manner as in Example 6, except that 24.6 g (195 mmol) of cyclooctanone was used instead of 16.4 g of cyclopentanone (yield: 60percent). The 1H-NMR data for the compound (M-8) is shown below. 1H-NMR (CDCl ) δ: 1.30-1.62 (m, 18H, CH ), 1.69 (s, 3H, CH ), 1.92-2.08 (m, 8H, CH ), 3.26-3.40 (m, 2H, CH ), 3 2 3 2 2 3.60-3.74 (m, 2H, CH2), 4.48 (s, 1H, CH), 5.36 (s, 1H, CH), 5.90 (s, 1H, CH). Patent; JSR Corporation; US2012/258402; (2012); (A1) English View in Reaxys

Rx-ID: 33995984 View in Reaxys 72/449 Yield 59%

Conditions & References 3 : Synthesis of Compound (M-3) 23.4 g of the compound shown by the following formula (M-3) (compound (M-3)) was obtained in the same manner as in Example 1, except that 22.5 g (150 mmol) of 2-adamantanone was used instead of 12.6 g of cyclopentanone (yield: 59percent). The 1H-NMR data for the compound (M-3) is shown below. 1H-NMR (CDCl ) δ: 1.25-2.24 (m, 23H, CH, CH , CH ), 2.54 (br, 1H, OH), 3.40 (t, 2H, CH ), 5.37 (s, 1H, CH), 5.89 3 2 3 2 (s, 1H, CH). Patent; JSR Corporation; US2012/258402; (2012); (A1) English View in Reaxys

56%

9 : Example 9 Example 9

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41.1 g of the compound shown by the following formula (M-9) (compound (M-9)) was obtained in the same manner as in Example 6, except that 29.3 g (195 mmol) of 2-adamantanone was used instead of 16.4 g of cyclopentanone (yield: 56percent). The 1H-NMR data for the compound (M-9) is shown below. 1H-NMR (CDCl ) δ: 1.22-2.50 (m, 30H, CH , CH ), 3.60 (t, 2H, CH ), 3.73 (t, 2H, CH ), 5.37 (s, 1H, CH), 5.89 (s, 1H, 3 2 3 2 2 CH). Patent; JSR Corporation; US2012/258402; (2012); (A1) English View in Reaxys

O O

Rx-ID: 34217802 View in Reaxys 73/449 Yield

Conditions & References Heating, Thermodynamic data, Kinetics, Pressure, Concentration, Time, Temperature Rosas, Felix; Lezama, Jesus; Mora, Jose R.; Maldonado, Alexis; Chuchani, Gabriel; Cordova, Tania; Journal of Physical Chemistry A: Molecules, Spectroscopy, Kinetics, Environment, and General Theory; vol. 116; nb. 37; (2012); p. 9228 - 9237,10 View in Reaxys O

Rx-ID: 30312920 View in Reaxys 74/449 Yield

Conditions & References 1 :Example 1Reaction of Cyclopentene with Dinitrogen MonoxideThe experiment according to Example 1 was performed in a plant with a construction according to schematic FIG. 1.Through stream (2), the fresh cyclopentene feed was metered in at 116.4 g/h. This originated from the distillation of a C5 cut from a steamcracker and had the following composition (percent by weight): cyclopentene (approx. 95.1percent), cyclopentane (approx. 3.4percent), 2methyl-2-butene (approx. 1.2percent).This stream was first mixed with stream (8) (return cyclopentene) in order to obtain a stream (3) which had the following composition: cyclopentene (approx. 46.3percent), cyclopentane (approx. 51.9percent), 2-methyl-2-butene (approx. 0.9percent), 2,2-dimethylbutane (approx. 0.81percent).This stream was then metered to the reactor (R) with a metering pump (flow rate: approx. 2076 g/h). Through stream (1), liquid N2O (N2O content >99.8percent by volume, from Messer Griesheim) was metered to the reactor at approx. 74 g/h. The molar cyclopentene:N2O ratio in the reactor feed was 0.11 mol/mol. The reactor consisted of a tube (external diameter=60.3 mm, wall thickness=2.4 mm, length=approx. 4 m). The reaction volume was (minus the volume of random packings), including connecting pieces, approx. 8 l in total.The tube was provided with an insulating jacket with an additional three-piece support heater which was set to (from the bottom) 256° C., 275° C. and 317° C. The cyclopentene conversion in straight pass was 11percent and the N2O conversion approx. 96percent. The reactor output (4) was, downstream of the pressure regulator, decompressed to 1 bar in two steps with two flash vessels (F) operated at 10 bar and 1 bar, and cooled. The gaseous components (stream (5)) were removed, and hydrocarbons present therein were very substantially condensed out in a downstream cooler (operated at +5° C., not shown in the diagram).The liquid phase (6) was separated in a distillation column (D) (bubble-cap tray column with 20 trays and liquid side draw). The bottom product (7) obtained was 138.7 g/h of a stream with the following composition: cyclopentanone (approx. 95.3percent by weight), cyclopentane (approx. 0.8percent by weight), 4-pentenal (approx. 1.3percent by weight), cyclopentene oxide (approx. 0.37percent by weight), cyclopentene dimers (approx. 0.53percent by weight), cyclopentene (approx. 0.08percent by weight).The side draw product, stream (8), which comprised 45.6percent cyclopentene, was recycled to the reactor via stream (3).At the top of the column, via the top stream (9), only very small amounts of low boilers (e.g. ethylene and acetaldehyde from the oxidation of 2-methyl-2-butene) were discharged. With Nitrous oxide, T= 256 - 317 °C , Industry scale Patent; BASF SE; US2011/46413; (2011); (A1) English View in Reaxys

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O HO

O OH

Rx-ID: 32318154 View in Reaxys 75/449 Yield

Conditions & References With zirconium(VI) oxide in ethanol, Time= 5h, T= 350 °C , Inert atmosphere Abe, Katsutoshi; Ohishi, Yusuke; Okada, Takuto; Yamada, Yasuhiro; Sato, Satoshi; Catalysis Today; vol. 164; nb. 1; (2011); p. 419 - 424 View in Reaxys

O HO

O OH

Rx-ID: 32318157 View in Reaxys 76/449 Yield

Conditions & References With cerium(IV) oxide in ethanol, Time= 5h, T= 350 °C , Inert atmosphere Abe, Katsutoshi; Ohishi, Yusuke; Okada, Takuto; Yamada, Yasuhiro; Sato, Satoshi; Catalysis Today; vol. 164; nb. 1; (2011); p. 419 - 424 View in Reaxys -1 F

(v4)

B FF

O+

Rx-ID: 37065326 View in Reaxys 77/449 Yield

Conditions & References in acetonitrile, T= 60 °C , Kinetics Lu, Yun; Bradshaw, Joshua; Zhao, Yu; Kuester, William; Kabotso, Daniel; Journal of Physical Organic Chemistry; vol. 24; nb. 12; (2011); p. 1172 - 1178 View in Reaxys

Rx-ID: 1792692 View in Reaxys 78/449 Yield 24 % Chromat., 13.2 % Chromat.

Conditions & References With KHBPh3 in tetrahydrofuran, Time= 2h, T= -78 °C Kim, Kwan Eung; Park, Soo Bong; Yoon, Nung Min; Synthetic Communications; vol. 18; nb. 1; (1988); p. 89 - 96 View in Reaxys With [(η5-C5Me5)2Rh2(μ-Cl)2Cl2], sodium formate, N-(2-amino-ethyl)-4-methyl-benzenesulphonamide in water, Time= 1h, T= 60 °C , Inert atmosphere, chemoselective reaction

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Li, Xuefeng; Li, Liangchun; Tang, Yuanfu; Zhong, Ling; Cun, Linfeng; Zhu, Jin; Liao, Jian; Deng, Jingen; Journal of Organic Chemistry; vol. 75; nb. 9; (2010); p. 2981 - 2988 View in Reaxys O

Rx-ID: 5311531 View in Reaxys 79/449 Yield

Conditions & References

95 %

With NaBO3, Time= 3h, T= 70 °C , Ionic liquid Bortolini, Olga; Nino, Antonio De; Garofalo, Angelo; Maiuolo, Loredana; Russo, Beatrice; Synthetic Communications; vol. 40; nb. 16; (2010); p. 2483 - 2487 View in Reaxys

65 %

With bis-trimethylsilanyl peroxide, sodium hydride in tetrahydrofuran, Time= 24h, T= 20 °C , Hydrolysis Shahi, Shatrughan P.; Vankar, Yashwant D.; Synthetic Communications; vol. 29; nb. 24; (1999); p. 4321 - 4325 View in Reaxys

Rx-ID: 29173431 View in Reaxys 80/449 Yield

Conditions & References

64 %

With bromo-dimethylsulfonium bromide, Time= 3h, T= 80 °C , Ionic liquid, Beckmann rearrangement Yadav, Lal Dhar S.; Garima; Srivastava, Vishnu P.; Tetrahedron Letters; vol. 51; nb. 4; (2010); p. 739 - 743 View in Reaxys

64 %

With bromo-dimethylsulfonium bromide, zinc(II) chloride in acetonitrile, Time= 3h, Reflux, Beckmann rearrangement Yadav, Lal Dhar S.; Patel, Rajesh; Srivastava, Vishnu P.; Synthesis; nb. 11; (2010); p. 1771 - 1776; Art.No: Z04310SS View in Reaxys O O

Rx-ID: 29525699 View in Reaxys 81/449 Yield

Conditions & References With toluene-4-sulfonic acid in benzene Oliveira, Cristina; Morais, Goreti Ribeiro; Imai, Masao; Inohae, Eiko; Yamamoto, Chishou; Mataka, Shuntaro; Thiemann, Thies; Journal of Chemical Research; nb. 3; (2010); p. 158 - 162 View in Reaxys

O O

O HO

rel-configuration

Rx-ID: 29537756 View in Reaxys 82/449 Yield 92 %

Conditions & References With Bu4N[Fe(CO)3(NO)] in hexane, T= 20 - 80 °C , Molecular sieve, Inert atmosphere

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Magens, Silja; Plietker, Bernd; Journal of Organic Chemistry; vol. 75; nb. 11; (2010); p. 3715 - 3721 View in Reaxys

O OH

Rx-ID: 29565195 View in Reaxys 83/449 Yield 85 %

Conditions & References With oxygen, VOCl3 in ethyl acetate, Time= 0.5h, T= 20 °C Kirihara, Masayuki; Yoshida, Katsumi; Noguchi, Takuya; Naito, Sayuri; Matsumoto, Nobuchika; Ema, Yukinori; Torii, Motoya; Ishizuka, Yuki; Souta, Ikuo; Tetrahedron Letters; vol. 51; nb. 28; (2010); p. 3619 - 3622 View in Reaxys

Rx-ID: 4768856 View in Reaxys 84/449 Yield

Conditions & References With [iron(II)(H2O)6](perchlorate)2 in pyridine, T= 25 °C , Kinetics, Product distribution Barton, Derek H. R.; Launay, Franck; Tetrahedron; vol. 53; nb. 43; (1997); p. 14565 - 14578 View in Reaxys 3 :In a 350-ml autoclave made of stainless steel SUS 316 and equipped with a stirrer were placed 70 g of the cyclopentyl hydroperoxide-containing liquid (with a cyclopentyl hydroperoxide concentration of 1.2 percent by weight) prepared in Referential Example 1, 10 g of a 20 percent by weight sodium carbonate aqueous solution (pH 11.5), and 0.035 mg of manganese acetate tetrahydrate (0.008 mg in terms of manganese (Mn)). The mixture in the autoclave was heated up to 130°C in a nitrogen atmosphere at 3.5 MPa (gauge pressure) and then, stirred for 1 hour. The resulting reaction mixture was analyzed and found to contain 1.03 g of cyclopentanone, 0.35 g of cyclopentanol, 0.06 g of cyclopentyl hydroperoxide, and 0.02 g of esters (0.01 g of cyclopentyl esters in terms of cyclopentanol). The conversion from cyclopentyl hydroperoxide was 92.7percent, the selectivity for cyclopentanone was 64.1percent and the selectivity of cyclopentanol was 10.3percent both on the basis of reacted cyclopentyl hydroperoxide. The production ratio (by mole) of cyclopentanone to cyclopentanol was 6.22. With Mn(CH3COO)2*4H2O, sodium carbonate in water, Time= 1h, T= 130 °C , p= 26252.6Torr , pH= 11.5, autoclave, Product distribution / selectivity Patent; DAICEL CHEMICAL INDUSTRIES, LTD.; EP2096097; (2009); (A1) English View in Reaxys 5 :In a 350-ml autoclave made of stainless steel SUS 316 and equipped with a stirrer were placed 70 g of the cyclopentyl hydroperoxide-containing liquid (with a cyclopentyl hydroperoxide concentration of 1.2 percent by weight) prepared in Referential Example 1 and 10 g of a 20 percent by weight sodium hydroxide aqueous solution (pH 14). The mixture in the autoclave was heated up to 130°C in a nitrogen atmosphere at 3.5 MPa (gauge pressure) and then, stirred for 1 hour. The resulting reaction mixture was analyzed and found to contain 0.63 g of cyclopentanone, 0.69 g of cyclopentanol, and 0.13 g of cyclopentyl hydroperoxide (0 g of esters). The conversion from cyclopentyl hydroperoxide was 84.9percent, the selectivity for cyclopentanone was 2.5percent and the selectivity for cyclopentanol was 67.1percent both on the basis of reacted cyclopentyl hydroperoxide. The production ratio (by mole) of cyclopentanone to cyclopentanol was 0.037. With sodium hydroxide in water, Time= 1h, T= 130 °C , p= 26252.6Torr , pH= 14, autoclave, Product distribution / selectivity Patent; DAICEL CHEMICAL INDUSTRIES, LTD.; EP2096097; (2009); (A1) English View in Reaxys

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S O

Rx-ID: 8805861 View in Reaxys 85/449 Yield

Conditions & References

94 %

With formyl formic acid, Amberlyst 15, Time= 0.05h, microwave irradiation Chavan; Soni; Kamat; Synlett; nb. 8; (2001); p. 1251 - 1252 View in Reaxys

88 %

With potassium superoxide, tetraethylammonium bromide in N,N-dimethyl-formamide, Time= 3h, T= 20 °C Singh, Satish Kumar; Singh, Krishna Nand; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 184; nb. 9; (2009); p. 2339 - 2343 View in Reaxys O

Rx-ID: 28395201 View in Reaxys 86/449 Yield

Conditions & References

90 %Chromat.

With 3-[{2-[4-(4-{2-[bis-(2-methoxycarbonyl-ethyl)-amino]-ethylcarbamoyl}-phenyldisulfanyl)-benzoylamino]-ethyl}-(2methoxycarbonyl-ethyl)-amino]-propionic acid methyl ester in benzene, Time= 2.5h, T= 20 °C , UV-irradiation Tsuboi, Takaaki; Takaguchi, Yutaka; Tsuboi, Sadao; Heteroatom Chemistry; vol. 20; nb. 1; (2009); p. 1 - 11 View in Reaxys

NH 2 O

NH O

HN N H

NH N

Rx-ID: 28722340 View in Reaxys 87/449 Yield

Conditions & References With sodium perchlorate, water, T= 37 °C , aq. buffer, Kinetics Vale, Nuno; Nogueira, Fatima; do Rosario, Virgilio E.; Gomes, Paula; Moreira, Rui; European Journal of Medicinal Chemistry; vol. 44; nb. 6; (2009); p. 2506 - 2516 View in Reaxys

O O

O OH

Rx-ID: 28871530 View in Reaxys 88/449 Yield

Conditions & References With iron(II) sulfate in water, acetonitrile

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Bernat, Virginie; Saffon, Nathalie; Maynadier, Marjorie; Vial, Henri; Andre-Barres, Christiane; Tetrahedron; vol. 65; nb. 36; (2009); p. 7372 - 7379 View in Reaxys

F Br F F

F B

(v4)

F F

(v2)

Br F

Rx-ID: 29040619 View in Reaxys 89/449 Yield

Conditions & References With ethanol, water in 1,4-dioxane, T= 50 °C , Inert atmosphere, Kinetics, Temperature Miyamoto, Kazunori; Shiro, Motoo; Ochiai, Masahito; Angewandte Chemie - International Edition; vol. 48; nb. 47; (2009); p. 8931 - 8934 View in Reaxys

O N N

H O

Rx-ID: 29117275 View in Reaxys 90/449 Yield

Conditions & References

68 %

With selenium(IV) oxide, dihydrogen peroxide in methanol, water, T= 20 °C , pH= 7, aq. phosphate buffer Smith III, Amos B.; Liu, Zhuqing; Simov, Vladimir; Synlett; nb. 19; (2009); p. 3131 - 3134 View in Reaxys HO C

Rx-ID: 29160077 View in Reaxys 91/449 Yield

Conditions & References

14.5 With dipotassium peroxodisulfate, 2BF4 (1-)*C24H53B4Cu4N4O17 (2+), water in acetonitrile, Time= 6h, T= 50 °C , p= %Chro15201Torr , Autoclave mat., 7 %Chromat. Kirillova, Marina V.; Kirillov, Alexander M.; Pombeiro, Armando J. L.; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2936 - 2948 View in Reaxys H 2N N

O NH

Rx-ID: 5144719 View in Reaxys 92/449 Yield 85 %

Conditions & References With Zr(HSO4)4, silica gel in hexane, Time= 0.42h, T= 20 °C Shirini; Zolfigol; Safari; Mohammadpoor-Baltork; Mirjalili; Tetrahedron Letters; vol. 44; nb. 40; (2003); p. 7463 7465 View in Reaxys

85 %

With (NH4)6[Mo7O24]*4H2O, dihydrogen peroxide in water, acetic acid, Time= 4h, T= 20 °C Ganguly, Nemai C.; Nayek, Subhasish; Barik, Sujoy Kumar; Dutta, Sanjoy; Journal of the Indian Chemical Society; vol. 85; nb. 7; (2008); p. 711 - 716

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View in Reaxys 83 %

With potassium peroxomonosulphate in water, acetic acid, Time= 0.7h, T= 40 - 45 °C , Oxidation Bose, D. Subhas; Vanajatha; Srinivas; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 7; (1999); p. 835 - 836 View in Reaxys

72 %

With ammonium chlorochromate on aluminum oxide in dichloromethane, Time= 6h, Heating, various conditions Zhang, Gui-Sheng; Gong, Hui; Yang, De-Hong; Chen, Mi-Feng; Synthetic Communications; vol. 29; nb. 7; (1999); p. 1165 - 1170 View in Reaxys With sodium perborate in acetic acid, Time= 2.2h, T= 40 °C , Oxidation Bandgar, B. P.; Zirange, Sangita M.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 36; nb. 8; (1997); p. 695 - 696 View in Reaxys With dimethylammonium chlorochromate, silica gel in diethyl ether, Time= 1h, Heating Zhang, Gui-Sheng; Chai, Bing; Synthetic Communications; vol. 30; nb. 10; (2000); p. 1849 - 1855 View in Reaxys Rx-ID: 27886160 View in Reaxys 93/449

Yield 5 - 14 %, 4 - 50 %, 2 10 %, 3 38 %, 12 %, 12 %

Conditions & References Furfural reacted quickly over the temperature range from 150 to 250° C. At 150° C., 74percent of furfural was converted during heat-up to temperature. As shown in FIG. 7, the major product at 150° C. was tetrahydrofuran-methanol (THF-MeOH) at 10percent with a lesser amount of γ-valerolactone (GVL) at 5percent. 1,4-pentanediol (14PDO) was a lesser intermediate that was converted further to 2-methyl-tetrahydrofuranxiii (MTHF) with 2percent remaining. The demethylated versions, γ-butyrolactone (GBL) and tetrahydrofuran (THF), were also found, as was 1,2-pentanediol (12PDO). As seen in FIG. 8, there was also a reaction pathway involving cyclopentanone as an early product that was subsequently hydrogenated to cyclopentanol and 1-pentanol. At the higher temperature of 200° C. 67percent of the furfural was converted during the heat-up. As shown in FIG. 9, the THF-MeOH remained the major product (22percent) but the GVL (5percent), 14PDO (10percent) and MTHF (3percent) product slate became more prominent. The 12PDO was slightly more prominent but the GBL and THF were less so. As seen in FIG. 10, the cyclopentanone product was no longer present but cyclopentanol and 1-pentanol remained through the end of the test. At the higher temperature of 250° C. as seen in FIG. 11, 94percent of the furfural was converted during heat-up. As shown in FIG. 11, the MTHF product became dominant (30percent) along with its intermediates, GVL (14percent) and 14PDO. The THF-MeOH product was formed initially (50percent) but reacted further to a low of 4percent (at) 4 h, perhaps to the THF (12percent). GBL, which was present early on, was similarly reacted to THF. The cyclopentanone pathway products represented in FIG. 12 was still evident but all three products were reacted further and no longer present by the end of the test, having probably broken down to methane. At 300° C. no furfural survived the heat-up period. The THF-MeOH product (10percent yield at time 0) was reacted further and disappeared after the first sample. MTHF was the major product (38percent (at) 0.5 h) with THF as the important subsequent product. The reverse equilibrium product slate highlighted by GVL and levulinic acid13 were also significant. The cyclopentanone product was found (12percent) at time 0 but was reduced to trace quantities by 1.5 h. The subsequent alcohol products were not found. xiiiElliott, D. C., Fyre, J. G., Jr. (1999) Hydrogenated 5-Carbon Compound and Method of Making. U.S. Pat. No. 5,883,266. With hydrogen, ruthenium, Time= 0 - 4h, T= 150 - 300 °C , Product distribution / selectivity Patent; Battelle Memorial Institute; US7425657; (2008); (B1) English View in Reaxys The furfural conversion chemistry was also much different for the palladium catalyzed case. Furfural reacted quickly at these conditions. It was found only in the initial samples from 150 and 200° C. tests. At 150° C. the main product was cyclopentanone. MTHF was present at slightly higher concentration than THF-MeOH. GVL was a lesser but significant product. As shown in FIG. 19, the MTHF and THF-MeOH were recovered from the 200° C. test at about the same concentration as at 150° C., but GVL was increased to the second most prevalent product. At the higher temperature of 200° C. the cyclopentanone product was noticeably converted to cyclopentanol, as seen in FIG. 20. At 250° C. MTHF was the largest product, as seen in FIG. 21. GVL and THF-MeOH were present in nearly equal amounts. Levulinic acid showed up early but was converted (to GVL) until it was gone by the end of the test. In FIG.

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22 the transition was obvious from the early production of cyclopentanone with its subsequent conversion to cyclopentanol and the final product, 1-pentanol. At 300° C. (see FIG. 23) the early production of levulinic acid led quickly to GVL and MTHF formation. Similarly GBL and THF formation were significant throughout, though the GBL was gone by the end of the test. As seen in FIG. 24, 1-pentanol was the major product present at the end of the test. With hydrogen, palladium, Time= 4h, T= 200 - 300 °C , Product distribution / selectivity Patent; Battelle Memorial Institute; US7425657; (2008); (B1) English View in Reaxys O

Cl Cl

Cl E

Cl Cl

Z Cl

E Cl

Cl Cl

Rx-ID: 28293944 View in Reaxys 94/449 Yield

Conditions & References 3; 4 :Example 3 A well stirred reactor has been fed continuously with dichloropropanol containing 0.223 g of 1,3dichloropropane and 2.93 g of 3-chloro-l-propanol per kg of dichloropropanol at a rate of 5.07 kg/h/1 of reactor, with a sodium hydroxide solution containing 500 g of NaOH per kg at rate of 2.83 kg/h/1 of reactor and with recycled water at a rate of 6.23 kg/h/1 of reactor . The reactor has been operated at a temperature of 45 0C and at a pressure of 1 bar. The reactor was fitted with an overflow system for withdrawal of the liquid reaction medium. The liquid reaction medium was biphasic. The lighter phase which contained the salt and a small quantity of organics has been stripped with steam and the condensate has been recycled to the reactor. The heavier phase which contained the major part of the epichlorohydrin formed in the reactor has been submitted continuously to a first distillation operation under vacuum in a packed column to separate epichlorohydrin, water and the low boiling point byproducts at the top of the column and the excess of dichloropropanol and the heavy byproducts at the bottom of the column. The top fraction, collected at a temperature of 60.80C under a pressure of 150 mbar, has been submitted continuously to a second distillation in a packed column to eliminate water and the low boiling byproducts. The bottom product has been collected at normal pressure at a temperature of 115.20C; it contained 0.35 g of 1,3-dichloropropane per kg. This product has been purified by a third operation of distillation that has been realized in a batchwise manner in a glass plate distillation column under vacuum at a pressure of 790 mbar. The epichlorohydrin which has been recovered as the main distillation fraction collected between 107.4 - 107.60C contained 0.34 g of 1,3- dichloropropane per kg and is named ECH 2. Example 4 A well stirred reactor has been fed continuously with dichloropropanol containing 0.013 g of 1,3-dichloropropane and 0.0026 g of 3-chloro-l-propanol <n="21"/>per kg of dichloropropanol at a rate of 5.93 kg/h/1 of reactor, with a sodium hydroxide solution containing 500 g of NaOH per kg at rate of 2.67 kg/h/1 of reactor and with recycled water at a rate of 5.83 kg/h/1 of reactor. The reactor has been operated at a temperature of 45 0C and at a pressure of 1 bar. The reactor was fitted with an overflow system for withdrawal of the liquid reaction medium. The liquid reaction medium was biphasic. The lighter phase which contained the salt and a small quantity of organics has been stripped with steam and the condensate has been recycled to the reactor. The heavier phase which contained the major part of the epichlorohydrin formed in the reactor has been submitted continuously to a first distillation operation in a packed column to separate epichlorohydrin, water and the low boiling point byproducts at the top of the column and the excess of dichloropropanol and the heavy by-products at the bottom of the column. The top fraction, collected at a temperature of 62.40C under a pressure of 150 mbar, has been submitted continuously to a second distillation in a packed column to eliminate water and the low boiling by-products as the top product and some heavy impurities at the bottom of the column. The epichlorohydrin has been collected by condensation of a gas phase collected from the middle of the column at normal pressure and at a temperature of 116.4 0C ; it contained 0.03 g of 1,3-dichloropropane per kg and is named ECH 5. The complete composition of epichlorohydrins ECH 2 and ECH 5 and of three other epichlorohydrin samples (ECH 1, ECH 3 and ECH 4) are presented in Table 1.Their compositions obtained by gas chromatography analysis. Table 1 <n="22"/>n.d. : not detected, n.m. : not measured <n="23"/>*: l-chloro-2, 3-epoxypropane amount calculated on the basis of the total content of other organic components With sodium hydroxide, water, T= 45 - 62.4 °C , p= 112.511 - 750.075Torr , Product distribution / selectivity Patent; SOLVAY; WO2009/773; (2008); (A1) English

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Cl OH

View in Reaxys

Rx-ID: 28506721 View in Reaxys 95/449 Yield

Conditions & References With hydrotalcite supported Cu nanoparticles in para-xylene, Time= 3h, T= 130 °C , Inert atmosphere Mitsudome, Takato; Mikami, Yusuke; Ebata, Kaori; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Chemical Communications; nb. 39; (2008); p. 4804 - 4806 View in Reaxys Br

O Br

racemate

Rx-ID: 11162087 View in Reaxys 96/449 Yield 87 %

Conditions & References With water, oxygen, lithium bromide, copper(ll) bromide in tetrahydrofuran, T= 25 °C , p= 760.051Torr Qaseer; Polish Journal of Chemistry; vol. 81; nb. 1; (2007); p. 31 - 38 View in Reaxys

Rx-ID: 5110107 View in Reaxys 97/449 Yield

Conditions & References With potassium carbonate, tris(triphenylphosphine)ruthenium(II) chloride, T= 56 °C , other catalysts, Mechanism Aranyos, Attila; Csjernyik, Gabor; Szabo, Kalman J.; Baeckvall, Jan-E.; Chemical Communications; nb. 4; (1999); p. 351 - 352 View in Reaxys With NADP embedded in ketoreductase preparation in phosphate buffer, hexane, Time= 4h, T= 24.99 °C , p= 750.075Torr , pH= 7.3, Equilibrium constant, Further Variations: Temperatures, Solvents, Pressures Tewari, Yadu B.; Phinney, Karen W.; Liebman, Joel F.; Journal of Chemical Thermodynamics; vol. 38; nb. 4; (2006); p. 388 - 395 View in Reaxys

NH 2

O NH

Rx-ID: 10144626 View in Reaxys 98/449 Yield 51 % Chromat., 32 % Chromat.

Conditions & References With aluminium, platinum on activated charcoal in water, Time= 0.166667h, microwave irradiation Miyazawa, Akira; Saitou, Kaori; Tanaka, Kan; Gaedda, Thomas M.; Tashiro, Masashi; Prakash, G. K. Surya; Olah, George A.; Tetrahedron Letters; vol. 47; nb. 9; (2006); p. 1437 - 1439 View in Reaxys

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O O

O E

Rx-ID: 10535370 View in Reaxys 99/449 Yield

Conditions & References With para-methoxybenzophenone, Time= 3.5h, Irradiation, Product distribution, Further Variations: Reagents, time Doohan, Roisin A.; Hannan, John J.; Geraghty, Niall W.A.; Organic and Biomolecular Chemistry; vol. 4; nb. 5; (2006); p. 942 - 952 View in Reaxys

HO O

Rx-ID: 11145451 View in Reaxys 100/449 Yield

Conditions & References

38 %

With N-butylamine in N,N,N',N',N'',N''-hexamethylphosphoric triamide, Time= 7h, T= 20 °C Singh, Chandan; Malik, Heetika; Synthesis; nb. 20; (2006); p. 3485 - 3489 View in Reaxys

O HO

OH O

Rx-ID: 24893300 View in Reaxys 101/449 Yield

Conditions & References

85 %, 10 %

9 :An operation was conducted in the same manner as in Example 2 except that cyclohexanol was replaced by an alicyclic secondary alcohol compound or an alicyclic ketone compound, both shown in Table 2 as a raw material compound. The results are shown in Table 2. With oxygen, trifluoroacetic acid, sodium nitrite, Time= 12.25h, T= 0 - 20 °C , Product distribution / selectivity Patent; TOKUYAMA CORPORATION; EP1728779; (2006); (A1) English View in Reaxys OH

O O

O HO

Rx-ID: 10199033 View in Reaxys 102/449 Yield 6%

Conditions & References in dichloromethane, Time= 4h, Photolysis Soltani, Omid; De Brabander, Jef K.; Angewandte Chemie - International Edition; vol. 44; nb. 11; (2005); p. 1696 1699 View in Reaxys O

O HO

OH O

Rx-ID: 102821 View in Reaxys 103/449 Yield 85 %

Conditions & References With carbon, Time= 0.5h, T= 450 °C

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Marquie; Laporterie; Dubac; Roques; Synlett; nb. 4; (2001); p. 493 - 496 View in Reaxys 84.2 %

With calcium hydroxide powder, T= 350 °C , Product distribution, Further Variations: Reagents Renz, Michael; Corma, Avelino; European Journal of Organic Chemistry; nb. 9; (2004); p. 2036 - 2039 View in Reaxys T= 290 °C Neunhoeffer; Paschke; Chemische Berichte; vol. 72; (1939); p. 919,927 View in Reaxys With barium carbonate, T= 290 - 300 °C Boedtker; Journal de Pharmacie et de Chimie; vol. <8> 15; (1932); p. 226 View in Reaxys With potassium fluoride, T= 250 - 280 °C Nesmejanow; Petscherskaja; Urezkaja; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1948); p. 240,243; ; (1948); p. 4924 View in Reaxys bei der Destillation im CO2-Strom Aschan; Chemische Berichte; vol. 45; (1912); p. 1605; Justus Liebigs Annalen der Chemie; vol. 383; (1911); p. 58 View in Reaxys With thorium(IV) dioxide, T= 350 °C , im CO2-Strom Sabatier; Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 987 View in Reaxys With MnO, T= 350 °C , im CO2-Strom Sabatier; Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 987 View in Reaxys With barium dihydroxide, T= 280 - 295 °C Patent; Bayer and Co.; DE256622; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 48 View in Reaxys With iron(II) sulfate, T= 280 - 295 °C Patent; Bayer and Co.; DE256622; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 48 View in Reaxys With uranium nitrate, T= 280 - 295 °C Patent; Bayer and Co.; DE256622; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 48 View in Reaxys With barium dihydroxide, T= 290 - 295 °C Patent; Bayer and Co.; DE256622; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 48 View in Reaxys Harries; Wagner; Justus Liebigs Annalen der Chemie; vol. 410; (1915); p. 39 View in Reaxys Harries; Wagner; ; 5 <New York 1925>, S. 37 View in Reaxys With acetic anhydride

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Blanc; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 144; (1907); p. 1357; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 779 View in Reaxys T= 313 - 320 °C , Destillation Vogel; Journal of the Chemical Society; (1929); p. 732 View in Reaxys With thorium(IV) dioxide, Destillation Zelinsky; Schuikin; Chemische Berichte; vol. 62; (1929); p. 2183; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 61; (1929); p. 2248 View in Reaxys With barytes Clutterbuck; Raper; Biochemical Journal; vol. 19; (1925); p. 393 View in Reaxys Zelinsky; Schuikin; Chemische Berichte; vol. 62; (1929); p. 2183; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 61; (1929); p. 2248 View in Reaxys Asmus,R.; View in Reaxys Wagner; Organic Syntheses; vol. 13; (1933); p. 110 View in Reaxys Vavon; Apchie; Bulletin de la Societe Chimique de France; vol. <4> 43; (1928); p. 670 View in Reaxys With barium dihydroxide, T= 285 - 300 °C Linstead; Meade; Journal of the Chemical Society; (1934); p. 935,942 View in Reaxys Thorpe; Kon; ; Vol. I <2. Ausg. 1941> 192 View in Reaxys Vogel; Journal of the Chemical Society; (1929); p. 732 View in Reaxys Mateju bei Vavon; Apchie; Bulletin de la Societe Chimique de France; vol. <4> 43; (1928); p. 668 Anm. 10 View in Reaxys

I O

Rx-ID: 9721420 View in Reaxys 104/449 Yield

Conditions & References With [bis(acetoxy)iodo]benzene, iodine in dichloromethane, Time= 0.0833333h, T= 20 °C , UV-irradiation Antunes, Carla S. Aureliano; Bietti, Massimo; Lanzalunga, Osvaldo; Salamone, Michela; Journal of Organic Chemistry; vol. 69; nb. 16; (2004); p. 5281 - 5289 View in Reaxys

O HO

Rx-ID: 9722938 View in Reaxys 105/449 Yield

Conditions & References With [bis(acetoxy)iodo]benzene, iodine in dichloromethane, Time= 0.0833333h, T= 20 °C , UV-irradiation

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Antunes, Carla S. Aureliano; Bietti, Massimo; Lanzalunga, Osvaldo; Salamone, Michela; Journal of Organic Chemistry; vol. 69; nb. 16; (2004); p. 5281 - 5289 View in Reaxys

O HO

Rx-ID: 9724530 View in Reaxys 106/449 Yield

Conditions & References With [bis(acetoxy)iodo]benzene, iodine in dichloromethane, Time= 0.25h, T= 20 °C , UV-irradiation Antunes, Carla S. Aureliano; Bietti, Massimo; Lanzalunga, Osvaldo; Salamone, Michela; Journal of Organic Chemistry; vol. 69; nb. 16; (2004); p. 5281 - 5289 View in Reaxys OH

Rx-ID: 9948664 View in Reaxys 107/449 Yield

Conditions & References With oxygen in acetonitrile, T= 13 °C , p= 760Torr , Irradiation, Product distribution, Further Variations: Reagents Takaki, Ken; Yamamoto, Jun; Komeyama, Kimihiro; Kawabata, Tomonori; Takehira, Katsuomi; Bulletin of the Chemical Society of Japan; vol. 77; nb. 12; (2004); p. 2251 - 2255 View in Reaxys O

O O

Rx-ID: 23655576 View in Reaxys 108/449 Yield 93 - 95 %

Conditions & References 1/2 With Al2O3#dotK2O in water, Time= 500h, T= 360 °C , p= 0.750075Torr Patent; BASF AKTIENGESELLSCHAFT; WO2004/76396; (2004); (A1) German View in Reaxys O

OH O

Rx-ID: 23663325 View in Reaxys 109/449 Yield 94 %, 7 %

Conditions & References 4 , T= 280 - 300 °C , Product distribution / selectivity Patent; BASF AKTIENGESELLSCHAFT; WO2004/76395; (2004); (A1) German View in Reaxys

77 %, 0.3 %

3 With sodium salt of phosphorous acid, T= 290 °C , Product distribution / selectivity Patent; BASF AKTIENGESELLSCHAFT; WO2004/76395; (2004); (A1) German View in Reaxys

73 %, 1 %

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With tin(IV) oxide, T= 270 °C , Product distribution / selectivity Patent; BASF AKTIENGESELLSCHAFT; WO2004/76395; (2004); (A1) German View in Reaxys 58 %, 25 %

5 With sodium hydroxide, T= 270 - 290 °C , Product distribution / selectivity Patent; BASF AKTIENGESELLSCHAFT; WO2004/76395; (2004); (A1) German View in Reaxys

39 %, 0.3 %

1 With anhydrous sodium borate, T= 290 °C , Product distribution / selectivity Patent; BASF AKTIENGESELLSCHAFT; WO2004/76395; (2004); (A1) German View in Reaxys

O HN N

Rx-ID: 9470483 View in Reaxys 110/449 Yield 90 %

Conditions & References With Zr(HSO4)4, silica gel in hexane, Time= 1.5h, Heating Shirini; Zolfigol; Safari; Mohammadpoor-Baltork; Mirjalili; Tetrahedron Letters; vol. 44; nb. 40; (2003); p. 7463 7465 View in Reaxys

O F O

racemate

Rx-ID: 9607228 View in Reaxys 111/449 Yield 6 % Chromat., 5 % Chromat., 3 % Chromat., 7 % Chromat.

Conditions & References in methanol, T= 120.05 °C , Further byproducts given Cafferata, Lazaro F. R.; Rimada, Ruben S.; Molecules; vol. 8; nb. 9; (2003); p. 655 - 662 View in Reaxys

F O

racemate F

Rx-ID: 9607229 View in Reaxys 112/449 Yield 18 % Chromat.,

Conditions & References in hexane, T= 120.05 °C , Kinetics, Further Variations: Solvents, Temperatures

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39 % Chromat., 5 % Chromat.

Cafferata, Lazaro F. R.; Rimada, Ruben S.; Molecules; vol. 8; nb. 9; (2003); p. 655 - 662 View in Reaxys

39 % Chromat., 18 % Chromat., 5 % Chromat.

in hexane, T= 120.05 °C Cafferata, Lazaro F. R.; Rimada, Ruben S.; Molecules; vol. 8; nb. 9; (2003); p. 655 - 662 View in Reaxys

O F O

F racemate

O O

F F

Rx-ID: 9607230 View in Reaxys 113/449 Yield

Conditions & References

3 % Chromat., 2.5 % Chromat., 7 % Chromat., 6 % Chromat.

in methanol, T= 120.05 °C , Further byproducts given Cafferata, Lazaro F. R.; Rimada, Ruben S.; Molecules; vol. 8; nb. 9; (2003); p. 655 - 662 View in Reaxys

F O

racemate F

Rx-ID: 9624050 View in Reaxys 114/449 Yield 13 % Chromat., 10 % Chromat., 6 % Chromat. 13 % Chromat., 10 % Chromat., 6 % Chromat.

Conditions & References in hexane, T= 120.05 °C , Kinetics, Further Variations: Solvents, Temperatures Cafferata, Lazaro F. R.; Rimada, Ruben S.; Molecules; vol. 8; nb. 9; (2003); p. 655 - 662 View in Reaxys

in hexane, T= 120.05 °C Cafferata, Lazaro F. R.; Rimada, Ruben S.; Molecules; vol. 8; nb. 9; (2003); p. 655 - 662 View in Reaxys

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O O

Rx-ID: 9129104 View in Reaxys 115/449 Yield

Conditions & References

33 %

With manganese(IV) oxide, aluminum oxide, T= 374.85 °C , Product distribution, Further Variations: Temperatures, Reagents, times Glinski; Kaszubski; Polish Journal of Chemistry; vol. 76; nb. 7; (2002); p. 1037 - 1039 View in Reaxys

O HO

Rx-ID: 9149253 View in Reaxys 116/449 Yield

Conditions & References

46 %, 11 %, 35 %

With methanesulfonic acid, oxygen, ammonium chloride, palladium diacetate, NPMoV, Time= 1h, T= 50 °C , p= 760.051Torr Yokota, Takahiro; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 67; nb. 14; (2002); p. 5005 - 5008 View in Reaxys

O HO

Rx-ID: 9246617 View in Reaxys 117/449 Yield

Conditions & References With 2-carboxypyrazine, dihydrogen peroxide, [Fe2(HPTB)(μ-OH)(NO3)2](NO3)2*CH3OH*2H2O in acetonitrile, Time= 6h, T= 25 °C , Product distribution, Kinetics, Further Variations: Reagents Nizova, Galina V.; Krebs, Bernt; Suess-Fink, Georg; Schindler, Siegfried; Westerheide, Lars; Gonzalez Cuervo, Laura; Shul'pin, Georgiy B.; Tetrahedron; vol. 58; nb. 45; (2002); p. 9231 - 9237 View in Reaxys

Rx-ID: 1980910 View in Reaxys 118/449 Yield 90 %

Conditions & References With cerium(III) chloride, silica gel, Time= 0.0666667h, Microwave irradiation Yadav; Subba Reddy; Reddy; Sabitha; Synlett; nb. 7; (2001); p. 1134 - 1136 View in Reaxys

70 %

With sodium perborate, sodium hydroxide, potassium dihydrogenphosphate, water in tert-butyl alcohol, Time= 24h, T= 60 °C Enders, Dieter; Bhushan, Vidya; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 42; nb. 12; (1987); p. 1595 - 1596 View in Reaxys

69 %

With iron nitrate (III) in dichloromethane, 30 min., r.t., then reflux Laszlo, Pierre; Polla, Eugenio; Tetrahedron Letters; vol. 25; nb. 31; (1984); p. 3309 - 3312 View in Reaxys

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20 %

With silica gel in tetrahydrofuran, water, Time= 10h, T= 25 °C Mitra, R. B.; Reddy, G. Bhaskar; Synthesis; nb. 9; (1989); p. 694 - 698 View in Reaxys

O Cl N

Rx-ID: 8677770 View in Reaxys 119/449 Yield

Conditions & References

40.4 %, 4.7 % Chromat., 54.9 % Chromat.

With phosphorus pentachloride, 1-n-butyl-3-methylimidazolium tetrafluoroborate, Time= 2h, T= 80 °C , Beckmann fragmentation Peng, Jiajian; Deng, Youquan; Tetrahedron Letters; vol. 42; nb. 3; (2001); p. 403 - 405 View in Reaxys

HO N

Rx-ID: 8777107 View in Reaxys 120/449 Yield

Conditions & References in tetrahydrofuran, Time= 1h, T= 20 °C , Photolysis Morgan; O'Connor; Humphrey; Buschman; Journal of Organic Chemistry; vol. 66; nb. 5; (2001); p. 1600 - 1606 View in Reaxys O

HO N N

Rx-ID: 8777108 View in Reaxys 121/449 Yield

Conditions & References in nitrobenzene, Time= 1h, T= 150 °C Morgan; O'Connor; Humphrey; Buschman; Journal of Organic Chemistry; vol. 66; nb. 5; (2001); p. 1600 - 1606 View in Reaxys in triglyme (triethylene glycol dimethyl ether), T= 200 °C Morgan; O'Connor; Humphrey; Buschman; Journal of Organic Chemistry; vol. 66; nb. 5; (2001); p. 1600 - 1606 View in Reaxys

O– N

OH Li+

Rx-ID: 8787103 View in Reaxys 122/449 Yield

Conditions & References in tetrahydrofuran, Time= 1h, T= 20 °C , Photolysis Morgan; O'Connor; Humphrey; Buschman; Journal of Organic Chemistry; vol. 66; nb. 5; (2001); p. 1600 - 1606 View in Reaxys

H N

poly(ε-caprolactam)

Rx-ID: 8796039 View in Reaxys 123/449

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Yield

Conditions & References T= 800 °C , Pyrolysis, Activation energy, Further Variations: Temperatures Herrera; Matuschek; Kettrup; Chemosphere; vol. 42; nb. 5-7; (2001); p. 601 - 607 View in Reaxys O

poly(ε-caprolactam)

Rx-ID: 8796041 View in Reaxys 124/449 Yield

Conditions & References T= 800 °C , Pyrolysis, Activation energy, Further Variations: Temperatures Herrera; Matuschek; Kettrup; Chemosphere; vol. 42; nb. 5-7; (2001); p. 601 - 607 View in Reaxys

polymer; monomers: hexamethylenediamine; adipic acid O

Rx-ID: 8796048 View in Reaxys 125/449 Yield

Conditions & References T= 800 °C , Pyrolysis, Activation energy, Further Variations: Temperatures Herrera; Matuschek; Kettrup; Chemosphere; vol. 42; nb. 5-7; (2001); p. 601 - 607 View in Reaxys

O O

Rx-ID: 8811616 View in Reaxys 126/449 Yield

Conditions & References

84 %

With Sodium bromate, ammonium chloride in water, acetonitrile, Time= 0.5h, T= 80 °C Shaabani; Karimi; Synthetic Communications; vol. 31; nb. 5; (2001); p. 759 - 765 View in Reaxys OH HO

OH O

Rx-ID: 8940085 View in Reaxys 127/449 Yield

Conditions & References With air, Manganese (II) acetate, N-hydroxy-4-dodecyloxycarbonylphthalimide, cobalt(II) 2,4-pentanedionate in ethanol, Time= 14h, T= 100 °C , p= 7600.51Torr , Product distribution, Further Variations: Reagents Sawatari; Yokota; Sakaguchi; Ishii; Journal of Organic Chemistry; vol. 66; nb. 23; (2001); p. 7889 - 7891 View in Reaxys

Si OH

racemate

Rx-ID: 8965276 View in Reaxys 128/449

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Yield

Conditions & References With sulfuric acid in 1,4-dioxane, toluene, T= 24.84 °C , Kinetics, Further Variations: Temperatures Mallya, M. Narendra; Nagendrappa, Gopalpur; Journal of the Chemical Society. Perkin Transactions 2; nb. 12; (2001); p. 2248 - 2252 View in Reaxys O

(CH3)2N-(CH=CH)2-CH(Y)N(CH3)2, Y=N(CH3)2 and OCH3

Rx-ID: 14732028 View in Reaxys 129/449 Yield

Conditions & References Reaction Steps: 2 1: (PCy3)2Cl2Ru=CHPh / 1,2-dichloro-ethane / 40 °C 2: H2 / (PCy3)2Cl2Rh=CHPh / 1,2-dichloro-ethane / 70 °C / 760.05 Torr With hydrogen, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, dichlorobis(tricyclohexylphosphine) (benzylidene)rhodium in 1,2-dichloro-ethane Louie; Bielawski; Grubbs; Journal of the American Chemical Society; vol. 123; nb. 45; (2001); p. 11312 - 11313 View in Reaxys O

Rx-ID: 15457237 View in Reaxys 130/449 Yield

Conditions & References Reaction Steps: 3 1: aq. NH4OH; hydroxylamine-O-sulfonic acid / methanol / 3.5 h / -20 - 20 °C 2: AgNO3; NaOH / H2O / 0.5 h 3: tetrahydrofuran / 1 h / 20 °C / Photolysis With ammonium hydroxide, sodium hydroxide, silver nitrate, hydroxylamine-o-sulphonic acid in tetrahydrofuran, methanol, water Morgan; O'Connor; Humphrey; Buschman; Journal of Organic Chemistry; vol. 66; nb. 5; (2001); p. 1600 - 1606 View in Reaxys Reaction Steps: 3 1: aq. NH4OH; hydroxylamine-O-sulfonic acid / methanol / 3.5 h / -20 - 20 °C 2: AgNO3; NaOH / H2O / 0.5 h 3: triethylene glycol dimethyl ether / 200 °C With ammonium hydroxide, sodium hydroxide, silver nitrate, hydroxylamine-o-sulphonic acid in methanol, triglyme (triethylene glycol dimethyl ether), water Morgan; O'Connor; Humphrey; Buschman; Journal of Organic Chemistry; vol. 66; nb. 5; (2001); p. 1600 - 1606 View in Reaxys

HN HN

Rx-ID: 15478941 View in Reaxys 131/449 Yield

Conditions & References Reaction Steps: 2 1: AgNO3; NaOH / H2O / 0.5 h 2: tetrahydrofuran / 1 h / 20 °C / Photolysis With sodium hydroxide, silver nitrate in tetrahydrofuran, water Morgan; O'Connor; Humphrey; Buschman; Journal of Organic Chemistry; vol. 66; nb. 5; (2001); p. 1600 - 1606 View in Reaxys

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Reaction Steps: 2 1: AgNO3; NaOH / H2O / 0.5 h 2: triethylene glycol dimethyl ether / 200 °C With sodium hydroxide, silver nitrate in triglyme (triethylene glycol dimethyl ether), water Morgan; O'Connor; Humphrey; Buschman; Journal of Organic Chemistry; vol. 66; nb. 5; (2001); p. 1600 - 1606 View in Reaxys

H N O

O N

N O

Rx-ID: 4873894 View in Reaxys 132/449 Yield 80 %

Conditions & References With ammonium chlorochromate on aluminum oxide in dichloromethane, Time= 6h, T= 35 - 40 °C Zhang, Gui-Sheng; Gong, Hui; Yang, De-Hong; Chen, Mi-Feng; Synthetic Communications; vol. 29; nb. 7; (1999); p. 1165 - 1170 View in Reaxys in dichloromethane, Time= 6h, T= 35 - 40 °C , Yield given Zhang, Gui-Sheng; Yang, De-Hong; Chen, Mi-Feng; Cai, Kun; Synthetic Communications; vol. 28; nb. 4; (1998); p. 607 - 611 View in Reaxys With aluminum oxide, dimethylammonium chlorochromate in dichloromethane, Time= 6h, T= 38 °C , Yield given Zhang, Gui-Sheng; Yang, De-Hong; Chen, Mi-Feng; Synthetic Communications; vol. 28; nb. 20; (1998); p. 3721 3725 View in Reaxys With aluminum oxide, Me3NHCrO3Cl in dichloromethane, Time= 8.5h, T= 38 °C , Yield given Zhang, Gui-Sheng; Yang, De-Hong; Chen, Mi-Feng; Organic Preparations and Procedures International; vol. 30; nb. 6; (1998); p. 713 - 716 View in Reaxys With dimethylammonium chlorochromate, silica gel in dichloromethane, Time= 0.2h, T= 38 - 40 °C Zhang, Gui-Sheng; Chai, Bing; Synthetic Communications; vol. 30; nb. 10; (2000); p. 1849 - 1855 View in Reaxys O

Rx-ID: 5285347 View in Reaxys 133/449 Yield 85 %, 1 %

Conditions & References With methanesulfonic acid, oxygen, palladium diacetate, molybdovanadophosphate/C in water, acetonitrile, Time= 6h, T= 50 °C , Wacker-type oxidation Kishi, Arata; Higashino, Takashi; Sakaguchi, Satoshi; Ishii, Yasutaka; Tetrahedron Letters; vol. 41; nb. 1; (2000); p. 99 - 102 View in Reaxys

6 %, 75 %

With methanesulfonic acid, oxygen, palladium diacetate, molybdovanadophosphate/C in ethanol, water, Time= 6h, T= 50 °C , Wacker-type oxidation Kishi, Arata; Higashino, Takashi; Sakaguchi, Satoshi; Ishii, Yasutaka; Tetrahedron Letters; vol. 41; nb. 1; (2000); p. 99 - 102 View in Reaxys

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Rx-ID: 8545793 View in Reaxys 134/449 Yield

Conditions & References

87.1 %, 12.9 %

in acetonitrile, Time= 48h, T= 25 °C , Hydrolysis, trifluoromethylthiolation Munavalli; Rohrbaugh; Rossman; Berg; Wagner; Durst; Synthetic Communications; vol. 30; nb. 16; (2000); p. 2847 - 2854 View in Reaxys O

O O

N O

Rx-ID: 8618348 View in Reaxys 135/449 Yield

Conditions & References With oxygen, nitrogen(II) oxide, chlorine, T= 22.85 °C , p= 700Torr , Irradiation, Oxidation, Product distribution, Further Variations: Pressures, Temperatures Orlando, John J.; Iraci, Laura T.; Tyndall, Geoffrey S.; Journal of Physical Chemistry A; vol. 104; nb. 21; (2000); p. 5072 - 5079 View in Reaxys O

O O

Rx-ID: 8627119 View in Reaxys 136/449 Yield

Conditions & References

18 %, 32 %, 30 %, 20 %

With titanium tetrachloride, T= -78 °C , Fragmentation, Product distribution, Further Variations: Reagents, Temperatures Dussault, Patrick H.; Lee, Hyung-Jae; Liu, Xuejun; Journal of the Chemical Society, Perkin Transactions 1; nb. 17; (2000); p. 3006 - 3013 View in Reaxys

Rx-ID: 8813162 View in Reaxys 137/449 Yield

Conditions & References With borax, dipotassium hydrogenphosphate in water, T= 30 °C , pH= 7, Kinetics Smirnov; Sevast'yanova; Russian Journal of Organic Chemistry; vol. 36; nb. 12; (2000); p. 1703 - 1708 View in Reaxys

HN HN

Rx-ID: 9134725 View in Reaxys 138/449

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Yield

Conditions & References With dimethylammonium chlorochromate, silica gel in diethyl ether, dichloromethane, Time= 0.5h, T= 38 - 40 °C Zhang, Gui-Sheng; Chai, Bing; Synthetic Communications; vol. 30; nb. 10; (2000); p. 1849 - 1855 View in Reaxys O

Rx-ID: 24294196 View in Reaxys 139/449 Yield

Conditions & References 5 : Synthesis of 2-Azacyclohexanone EXAMPLE 5 Synthesis of 2-Azacyclohexanone Following the procedure of Example 1 and substituting cyclopentanone for cyclooctanone, 2-azacyclohexanone is prepared. Patent; Emisphere Technologies, Inc.; US6084112; (2000); (A1) English View in Reaxys

Rx-ID: 585048 View in Reaxys 140/449 Yield 69 %

Conditions & References With bis(cyclopentadienyl)titanium dichloride, isopropylmagnesium bromide in tetrahydrofuran, diethyl ether, Time= 4h, Ambient temperature Yu, Yongping; Zhang, Yongmin; Synthetic Communications; vol. 29; nb. 2; (1999); p. 243 - 247 View in Reaxys

65 %

With sodio-propane-1,2-diol in anhydrous propane-1,2-diol, Time= 0.5h, T= 80 - 85 °C Aneja, R.; Hollis, W. M.; Davies A. P.; Eaton, G.; Tetrahedron Letters; vol. 24; nb. 43; (1983); p. 4641 - 4644 View in Reaxys With sulfuric acid Dieckmann; Justus Liebigs Annalen der Chemie; vol. 317; (1901); p. 104 View in Reaxys O

O O

Rx-ID: 5104311 View in Reaxys 141/449 Yield 8 %, 92 %

Conditions & References With dihydrogen peroxide, methyltrioxorhenium (VII), sodium bromide, Time= 10h, Ambient temperature Espenson; Zhu; Zauche; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1191 - 1196 View in Reaxys

Rx-ID: 5188102 View in Reaxys 142/449 Yield 99 %

Conditions & References With oxygen, kieselguhr, copper(l) chloride in hexane, Time= 2.5h, Heating, Oxidation

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Hashemi, Mohammed M.; Ahmadi Beni, Yousef; Journal of Chemical Research - Part S; nb. 7; (1999); p. 434 435 View in Reaxys OH

Rx-ID: 5199519 View in Reaxys 143/449 Yield

Conditions & References

89 % Chromat., 10 % Chromat.

With zirconium orthophosphate, Time= 15h, T= 305 °C , Dehydration, Product distribution, Further Variations: Reagents Al-Qallaf, Fawzia A. H.; Johnstone, Robert A. W.; Liu, Jun-Yao; Lu, Ling; Whittaker, David; Journal of the Chemical Society. Perkin Transactions 2; nb. 7; (1999); p. 1421 - 1423 View in Reaxys

O O

O S O

HO O O

Rx-ID: 4923730 View in Reaxys 144/449 Yield 64 %

Conditions & References in benzene, Heating Bender, John A.; Daves, Samantha; West; Tetrahedron Letters; vol. 39; nb. 15; (1998); p. 2051 - 2054 View in Reaxys

O O

Rx-ID: 4924656 View in Reaxys 145/449 Yield

Conditions & References With ruthenium trichloride, T= 20 °C , Yield given. Yields of byproduct given Launay, Franck; Roucoux, Alain; Patin, Henri; Tetrahedron Letters; vol. 39; nb. 11; (1998); p. 1353 - 1356 View in Reaxys

O O

OH O

S O

O O

S O

Rx-ID: 4928372 View in Reaxys 146/449 Yield 68 %

Conditions & References in benzene, Heating

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Bender, John A.; Daves, Samantha; West; Tetrahedron Letters; vol. 39; nb. 15; (1998); p. 2051 - 2054 View in Reaxys

OH O

Rx-ID: 4932537 View in Reaxys 147/449 Yield

Conditions & References With tert.-butylhydroperoxide, ruthenium trichloride, T= 20 °C , Yield given. Yields of byproduct given Launay, Franck; Roucoux, Alain; Patin, Henri; Tetrahedron Letters; vol. 39; nb. 11; (1998); p. 1353 - 1356 View in Reaxys Cl

2 Cl

Rx-ID: 4967817 View in Reaxys 148/449 Yield

Conditions & References in cyclohexane, T= 24.9 °C , Equilibrium constant Abraham, Michael H.; Prior, David V.; Schulz, Ronald A.; Morris, Jeffrey J.; Taylor, Peter J.; Journal of the Chemical Society - Faraday Transactions; vol. 94; nb. 7; (1998); p. 879 - 885 View in Reaxys Cl

Rx-ID: 4967830 View in Reaxys 149/449 Yield

Rx-ID: 5013320 View in Reaxys 150/449 Yield

Conditions & References With air, sodium acetate, palladium diacetate, bathophenanthroline disulfonate disodium salt in water, Time= 10h, T= 100 °C , p= 22501.8Torr , Yield given. Title compound not separated from byproducts Brink, Gerd-Jan Ten; Arends, Isabel W. C. E.; Papadogianakis, Georgios; Sheldon, Roger A.; Chemical Communications; nb. 21; (1998); p. 2359 - 2360 View in Reaxys

Rx-ID: 5052864 View in Reaxys 151/449 Yield 52 %

Conditions & References With Oxonereg; in water, acetone, acetonitrile, Time= 10h, T= 45 °C , pH= 7.5, Oxidation

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Bose, D. Subhas; Vanajatha; Synthetic Communications; vol. 28; nb. 24; (1998); p. 4531 - 4535 View in Reaxys O O

O O

O O O

Rx-ID: 5113467 View in Reaxys 152/449 Yield

Conditions & References

8 %, 55 %, With 9,10-dicyanoanthracene, triphenylphosphine in water, N,N-dimethyl-formamide, isopropyl alcohol, Irradiation 5% Pandey, Ganesh; Ghorai, Manas K.; Hajra, Saumen; Tetrahedron Letters; vol. 39; nb. 45; (1998); p. 8341 - 8344 View in Reaxys

O O

Rx-ID: 4699185 View in Reaxys 153/449 Yield

Conditions & References With triphenylphosphine in chloroform-d1, Time= 24h, T= 50 °C , Product distribution Griesbaum, Karl; Liu, Xuejun; Dong, Yuxiang; Tetrahedron; vol. 53; nb. 15; (1997); p. 5463 - 5470 View in Reaxys O

O O

Rx-ID: 4699186 View in Reaxys 154/449 Yield

Conditions & References With triphenylphosphine in chloroform-d1, Time= 48h, T= 50 °C , Product distribution Griesbaum, Karl; Liu, Xuejun; Dong, Yuxiang; Tetrahedron; vol. 53; nb. 15; (1997); p. 5463 - 5470 View in Reaxys

Rx-ID: 4776255 View in Reaxys 155/449 Yield 7 %, 48 %

Conditions & References With tris(cetyl)pyridinium 12-tungstophosphate, dihydrogen peroxide in dichloromethane, Time= 9h, T= 20 °C Yamamoto, Hiroyo; Tsuda, Masaya; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 62; nb. 21; (1997); p. 7174 - 7177 View in Reaxys

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O O

Rx-ID: 5053558 View in Reaxys 156/449 Yield

Conditions & References

46 % Chromat., 12 % Chromat.

With nitrogen(IV) oxide, ozone in dichloromethane, Time= 3h, T= 0 °C , Oxidation, nitration Suzuki, Hitomi; Takeuchi, Toyomi; Mori, Tadashi; Bulletin of the Chemical Society of Japan; vol. 70; nb. 12; (1997); p. 3111 - 3115 View in Reaxys OH

cyclopentenone Rx-ID: 8501402 View in Reaxys 157/449 Yield

Conditions & References

85 % Chromat.

With Amberlite IRA-400, borohydride form, copper(II) sulfate in methanol, Time= 0.25h, T= 20 °C , Reduction Sim, Tae Bo; Yoon, Nung Min; Bulletin of the Chemical Society of Japan; vol. 70; nb. 5; (1997); p. 1101 - 1107 View in Reaxys OH

O 2H

Rx-ID: 4442065 View in Reaxys 158/449 Yield

Conditions & References With lithium diisopropyl amide in benzene, further solvents; primary kinetic deuterium isotope effects in benzene and ethers; reaction half-life - 15-30 min at 0 deg C; effect of 12-crown-4, Product distribution, Mechanism Morgan, Kathleen M.; Gajewski, Joseph J.; Journal of Organic Chemistry; vol. 61; nb. 3; (1996); p. 820 - 821 View in Reaxys

O Br–

N+

H N

H 2N

Rx-ID: 4568699 View in Reaxys 159/449 Yield

Conditions & References With NOBF4, multistep r., 1.) CH2Cl2, -78 deg C, 2 h; 2.) CH2Cl2, CH3CN, r.t., 1 h; nitrosation products depend on reaction conditions and type of the nucleophile, Product distribution Alvarez, Roberto Martinez; Vazquez, Angel Sanchez; Hananck, Michael; Subramanian; Journal of Physical Organic Chemistry; vol. 9; nb. 4; (1996); p. 227 - 233 View in Reaxys

Rx-ID: 4572744 View in Reaxys 160/449 Yield

Conditions & References With water-d2, nitrosonium tetrafluoroborate, multistep r., 1.) CH2Cl2, -78 deg C, 2 h; 2.) CH2Cl2, CH3CN, r.t., 1 h; nitrosation products depend on reaction conditions and type of the nucleophile, Product distribution

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Alvarez, Roberto Martinez; Vazquez, Angel Sanchez; Hananck, Michael; Subramanian; Journal of Physical Organic Chemistry; vol. 9; nb. 4; (1996); p. 227 - 233 View in Reaxys

O N+

I–

Rx-ID: 4592553 View in Reaxys 161/449 Yield

Conditions & References With sodium hydroxide, potassium carbonate, 1) heating, 2) drying, Yield given. Multistep reaction Kukharev; Russian Chemical Bulletin; vol. 45; nb. 4; (1996); p. 885 - 889 View in Reaxys Cl

Cl OH

O OH

racemate

Rx-ID: 4607011 View in Reaxys 162/449 Yield

Conditions & References With triethylammonium phosphinate, (R)-BINAP-Ru, Time= 3h, T= 40 °C , diastereoselectivity investigated; yield depends on the type of catalysts and solvents; various substrates investigated, Product distribution Khai, Bui The; Arcelli, Antonio; Tetrahedron Letters; vol. 37; nb. 36; (1996); p. 6599 - 6602 View in Reaxys Cl

O OH

racemate

Rx-ID: 4607012 View in Reaxys 163/449 Yield

Conditions & References With triethylammonium phosphinate, tris(triphenylphosphine)ruthenium(II) chloride, Time= 3h, T= 40 °C , Yield given. Yields of byproduct given Khai, Bui The; Arcelli, Antonio; Tetrahedron Letters; vol. 37; nb. 36; (1996); p. 6599 - 6602 View in Reaxys

O OH

racemate

Rx-ID: 4662977 View in Reaxys 164/449 Yield

Conditions & References With triethylammonium phosphinate, tris(triphenylphosphine)ruthenium(II) chloride in methanol, Time= 3h, T= 40 °C , Yield given. Yields of byproduct given Khai, Bui The; Arcelli, Antonio; Tetrahedron Letters; vol. 37; nb. 36; (1996); p. 6599 - 6602 View in Reaxys O

Rx-ID: 4251100 View in Reaxys 165/449

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Yield

Conditions & References T= 440.5 °C , var. temp., Ea, Rate constant, Thermodynamic data, Product distribution Al-Awadi, Nouria A.; Mathew, Tommy; International Journal of Chemical Kinetics; vol. 27; nb. 9; (1995); p. 843 848 View in Reaxys O O

Rx-ID: 3645513 View in Reaxys 166/449 Yield

Conditions & References With lithium boron tetrafluoride in acetonitrile, Time= 0.5h, Heating, var. reag.: 0.1M HF in water, 15 min, RT, Product distribution Lillie; Avery; Tetrahedron Letters; vol. 35; nb. 7; (1994); p. 969 - 972 View in Reaxys O

O O

Rx-ID: 3647228 View in Reaxys 167/449 Yield

Conditions & References

93 % Chromat.

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, water, Ambient temperature McDonald, Chriss E.; Nice, Lois E.; Kennedy, Kenneth E.; Tetrahedron Letters; vol. 35; nb. 1; (1994); p. 57 - 60 View in Reaxys

O O

O HO

Rx-ID: 4075308 View in Reaxys 168/449 Yield

Conditions & References With perchloric acid in 1,4-dioxane, ΔH, Thermodynamic data Wiberg, Kenneth B.; Morgan, Kathleen M.; Maltz, Henry; Journal of the American Chemical Society; vol. 116; nb. 24; (1994); p. 11067 - 11077 View in Reaxys 2H

Rx-ID: 4095423 View in Reaxys 169/449 Yield

Conditions & References With water-d2, T= 10 - 40 °C , ΔH, ΔG, ΔS, Thermodynamic data, Equilibrium constant Wiberg, Kenneth B.; Morgan, Kathleen M.; Maltz, Henry; Journal of the American Chemical Society; vol. 116; nb. 24; (1994); p. 11067 - 11077 View in Reaxys

O Cl

NH 2

Rx-ID: 24511469 View in Reaxys 170/449

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Yield

Conditions & References 4 : PREPARATION 4 STR23 PREPARATION 4 STR23 To a solution of concentrated hydrochloric acid (23 mL, 0.28 mol) in 90 mL of water at -5° C. is added a solution of 3,5-dichloroaniline (15.0 g, 93 mmol) in 10 mL THF. The reaction mixture is allowed to stir at -5° C. for 20 minutes and a solution of sodium nitrite (6.4 g, 93 mmol) in 20 mL of water is added slowly. The reaction mixture is kept below 0° C. with stirring until most of the solid went into solution (ca. 30 minutes), the diazonium salt solution is then kept at 0° C. for further use. A potassium hydroxide (16.3 g, 0.29 mol) in 120 mL is prepared and cooled to 0° C. Methyl 2-oxocyclopentanecarboxylate (12.9 g, 91 mmol) is placed in a separatory funnel and was shaken vigorously with 60 mL of the KOH solution. Benzene (15 mL) is then added to extract out the unreacted cyclopentanone. The aqueous layer is collected and the benzene layer is reextracted with the remaining potassium hydroxide solution. The aqueous layers are poured onto 150 g of ice followed by the addition of the diazonium salt solution. The solid formed is collected and dissolved in 500 mL of chloroform. The chloroform solution is washed once with brine and dried with magnesium sulphate. The solid product obtained after filtration and concentration is triturated with ether-hexane mixture. The yellow solid is then collected by filtration and air dried: 1 H NMR (DMSO-d6, 200 MHz) δ 12.25 (s, 1H), 10.28 (s, 1H), 7.23 (d, 2H, J=1.81 Hz), 7.07 (t, 1H, J=1.81 Hz), 3.76 (s, 3H), 2.59 (t, 2H), J=8.12 Hz), 2.30 (t, 2H, J=7.27 Hz), 1.65 (m, 2H). With hydrogenchloride, sodium nitrite in tetrahydrofuran, potassium hydroxide, water, benzene Patent; Warner-Lambert Company; US5284862; (1994); (A1) English View in Reaxys

O S S

Rx-ID: 2835200 View in Reaxys 171/449 Yield

Conditions & References

98 %

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile, Time= 2h, T= 20 - 25 °C , Irradiation Mathew, Lizamma; Sankararaman, S.; Journal of Organic Chemistry; vol. 58; nb. 26; (1993); p. 7576 - 7577 View in Reaxys O O

O O

Rx-ID: 2934985 View in Reaxys 172/449 Yield

Conditions & References

85 % Chromat., 2 % Chromat., 9 % Chromat.

With oxygen, H5PV2Mo10O40(1,11) in acetonitrile, Time= 4h, T= 60 °C , p= 760Torr , various catalysts, solvents, and reaction times, Product distribution Atlamsani, Ahmed; Bregeault, Jean-Marie; Ziyad, Mahfoud; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5663 - 5665 View in Reaxys O

H6 PV3 Mo9 O40 Rx-ID: 24423089 View in Reaxys 173/449

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Yield

Conditions & References 10 : EXAMPLE 10 EXAMPLE 10 An autoclave was charged with a solution of 0.20 mmol (0.0482 gram) of PdSO4.2H 2 O and 1.8 mmol (3.52 grams; water content, 13.3percent by weight) of H6 PV3 Mo9 O40 in 25 ml of 1,4-dioxane and 5 ml of water, and 147 mmol (10.0 grams) of cyclopentene was added to the solution. Thereafter, the pressure within the autoclave was elevated to 8.5 kg/cm2 (gauge pressure) by supplying nitrogen at 60° C. and then to the total pressure of 10 kg/cm2 (gauge pressure) by supplying oxygen. The reaction was carried out in this state for 120 minutes at the pressure of 10 kg/cm2 (Gauge pressure) by supplying oxygen. As a result, cyclopentanone and 2-cyclopenten-1-one were yielded in the quantities of 11.2 mmol and 8.7 mmol, respectively. No undissolved materials, such as sediment, were found in the reaction solution after completion of the reaction. in 1,4-dioxane, water Patent; Kemitsu Kosan Company Limited; US5237103; (1993); (A1) English View in Reaxys

2H 2H 2H

(v4)

(v4) N 2(v4) H Pd (v4)N

(v1)

Rx-ID: 26905448 View in Reaxys 174/449 Yield

Conditions & References in dichloromethane-d2, monitored by NMR Beck, I. E.; Gusevskaya, E. V.; Golovin, A. V.; Likholobov, V. A.; Journal of Molecular Catalysis; vol. 83; (1993); p. 301 - 310 ; (from Gmelin) View in Reaxys HO

O I

Rx-ID: 1515147 View in Reaxys 175/449 Yield

Conditions & References

39 %, 36 %

With iodo trichloro silane Elmorsy, Saad S.; Bhatt, M. V.; Pelter, Andrew; Tetrahedron Letters; vol. 33; nb. 12; (1992); p. 1657 - 1660 View in Reaxys

Rx-ID: 1651742 View in Reaxys 176/449 Yield

Conditions & References

39 %, 86 %

With iodo trichloro silane, Time= 1h, Ambient temperature Elmorsy, Saad S.; Bhatt, M. V.; Pelter, Andrew; Tetrahedron Letters; vol. 33; nb. 12; (1992); p. 1657 - 1660 View in Reaxys

Rx-ID: 1743703 View in Reaxys 177/449

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Yield

Conditions & References

39 %, 78 %

With iodo trichloro silane Elmorsy, Saad S.; Bhatt, M. V.; Pelter, Andrew; Tetrahedron Letters; vol. 33; nb. 12; (1992); p. 1657 - 1660 View in Reaxys

(v1)

Rx-ID: 1978587 View in Reaxys 178/449 Yield

Conditions & References With oxygen, chlorine, T= -30.1 °C , p= 760Torr , Irradiation, temp.range from 243 K to 373 K; different oxygen partial pressure, Kinetics Rowley, David M.; Lightfoot, Phillip D.; Lesclaux, Robert; Wallington, Timothy J.; Journal of the Chemical Society, Faraday Transactions; vol. 88; nb. 10; (1992); p. 1369 - 1376 View in Reaxys

S S

Rx-ID: 1999265 View in Reaxys 179/449 Yield

Conditions & References With sodium hydrogensulfide, dihydrogen peroxide, ferric picolinate complexes in pyridine, acetic acid, Ambient temperature, Title compound not separated from byproducts Balavoine; Barton; Gref; Lellouche; Tetrahedron; vol. 48; nb. 10; (1992); p. 1883 - 1894 View in Reaxys

OH O HO

Rx-ID: 2003316 View in Reaxys 180/449 Yield

Conditions & References With air, 3,7,10-Ph3-2,4,6,8-tetraoxodipyrimidine, Time= 25h, T= 115 °C , other catalysts, Product distribution, Mechanism Nagamatsu, Tomohisa; Yamato, Hirotake; Ono, Masami; Takarada, Shigeki; Yoneda, Fumio; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 16; (1992); p. 2101 2110 View in Reaxys O

O O

Rx-ID: 2347278 View in Reaxys 181/449 Yield 19 %, 52 %

Conditions & References With cobalt(II) chloride in acetonitrile, Time= 8h, T= 70 °C Iqbal, Javed; Srivastava, Rajiv Ranjan; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2001 - 2007

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View in Reaxys O O

Rx-ID: 2347302 View in Reaxys 182/449 Yield

Conditions & References

13 %, 37 %

With cobalt(II) chloride in acetonitrile, Time= 10h, T= 80 °C Iqbal, Javed; Srivastava, Rajiv Ranjan; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2001 - 2007 View in Reaxys

H 2N

O N

H 2N

NH 2 O

Rx-ID: 3211908 View in Reaxys 183/449 Yield

Conditions & References With sodium hydroxide in acetonitrile, T= 34 °C , var. temp., Rate constant Sola, Regine; Commeyras, Auguste; Journal of Chemical Research, Miniprint; nb. 6; (1992); p. 1358 - 1370 View in Reaxys

(v1)

OH O

O O

CO2, HCl

Rx-ID: 7072109 View in Reaxys 184/449 Yield

Conditions & References With oxygen, chlorine, T= 21.9 °C , p= 700Torr , Irradiation, other pressures, other temp., Product distribution, Mechanism Rowley, David M.; Lightfoot, Phillip D.; Lesclaux, Robert; Wallington, Timothy J.; Journal of the Chemical Society, Faraday Transactions; vol. 88; nb. 10; (1992); p. 1369 - 1376 View in Reaxys

Rx-ID: 1487948 View in Reaxys 185/449 Yield

Conditions & References With ammonium chloride, hydroxocobalamine hydrochloride, zinc in water, Time= 6h, Heating, internal standard cyclohexanol, isomerization, different solvents (also deuterated ones), different reaction times, Product distribution Bonhote, Pierre; Scheffold, Rolf; Helvetica Chimica Acta; vol. 74; nb. 7; (1991); p. 1425 - 1444 View in Reaxys

Rx-ID: 1487949 View in Reaxys 186/449

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Yield

Conditions & References

5.5 %, 0.5 %, 30 %

With ammonium chloride, hydroxocobalamine hydrochloride, zinc in methanol, Time= 96h, Ambient temperature, dark, isomerization, different solvents (also deuterated ones), different temperatures, ΔH(excit.), ΔS(excit.), Product distribution, Equilibrium constant, Kinetics Bonhote, Pierre; Scheffold, Rolf; Helvetica Chimica Acta; vol. 74; nb. 7; (1991); p. 1425 - 1444 View in Reaxys

Rx-ID: 1619641 View in Reaxys 187/449 Yield 25 % Chromat., 52 % Chromat., 12 % Chromat.

Conditions & References With oxygen, N(Et)4ClO4 in N,N-dimethyl-formamide, T= 20 °C , other substituted cycloketones and alkyl carboxylates; electrolysis, Mechanism Carelli, Italo; Curulli, Antonella; Inesi, Achille; Zeuli, Errico; Journal of Chemical Research, Miniprint; nb. 1; (1991); p. 183 - 197 View in Reaxys

O HO

OH O

Rx-ID: 2003320 View in Reaxys 188/449 Yield

Conditions & References With dihydrogen peroxide, methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate, Time= 1.25h, T= 90 °C , Yield given Venturello, Carlo; Gambaro, Mario; Journal of Organic Chemistry; vol. 56; nb. 20; (1991); p. 5924 - 5931 View in Reaxys

O O O

Rx-ID: 2081825 View in Reaxys 189/449 Yield

Conditions & References

22 %, 6 %, With ozone in pentane, T= 0 °C 13 % Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Chemische Berichte; vol. 124; nb. 2; (1991); p. 391 396 View in Reaxys 22 %, 6 %, With ozone in pentane, T= 0 °C , other cycloalkylidenecycloalkanes 13 % Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Chemische Berichte; vol. 124; nb. 2; (1991); p. 391 396 View in Reaxys

O O O

Rx-ID: 2081829 View in Reaxys 190/449 Yield 60 %, 6 %

Conditions & References With ozone in polyethylene, Time= 10h, T= -75 °C , other cycloalkylidenecycloalkanes

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Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Chemische Berichte; vol. 124; nb. 2; (1991); p. 391 396 View in Reaxys 6 %, 60 %

With ozone in polyethylene, Time= 10h, T= -75 °C Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Chemische Berichte; vol. 124; nb. 2; (1991); p. 391 396 View in Reaxys O

O O O

Rx-ID: 2113586 View in Reaxys 191/449 Yield

Conditions & References

3 %, 62 %

With ozone in polyethylene, Time= 0.15h, T= -75 °C Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Chemische Berichte; vol. 124; nb. 2; (1991); p. 391 396 View in Reaxys O

O O

O HO

Rx-ID: 2477701 View in Reaxys 192/449 Yield

Conditions & References in chloroform-d1, Time= 408h, T= 60 °C , other ozonides Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Chemische Berichte; vol. 124; nb. 2; (1991); p. 391 396 View in Reaxys O O O

Rx-ID: 2477702 View in Reaxys 193/449 Yield

Conditions & References

14 %, 16 in pentane, Time= 8h, T= -20 °C , Irradiation %, 7 %, 45 Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Chemische Berichte; vol. 124; nb. 2; (1991); p. 391 % 396 View in Reaxys O O O

Rx-ID: 2477703 View in Reaxys 194/449 Yield

Conditions & References With triphenylphosphine in chloroform-d1, Time= 72h, T= 60 °C , other ozonides Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Chemische Berichte; vol. 124; nb. 2; (1991); p. 391 396 View in Reaxys

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O O

Rx-ID: 2477894 View in Reaxys 195/449 Yield

Conditions & References

24 %

in pentane, Time= 8h, T= -20 °C , Irradiation, Further byproducts given. Yields of byproduct given Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Chemische Berichte; vol. 124; nb. 2; (1991); p. 391 396 View in Reaxys

P O

O O

Rx-ID: 3873339 View in Reaxys 196/449 Yield

Conditions & References With oxygen, iron(III) chloride, zinc, 1) pyridine, acetic acid, 0 deg C, 2 h 2) r.t., 5 h, Yield given. Multistep reaction. Yields of byproduct given Barton; Beviere; Doller; Tetrahedron Letters; vol. 32; nb. 36; (1991); p. 4671 - 4674 View in Reaxys

Rx-ID: 1619642 View in Reaxys 197/449 Yield

Conditions & References

68 % Chromat., 15 % Chromat.

With (Et3NH)3PO4 in N,N-dimethyl-formamide, electrochemical reduction Carelli, Italo; Curulli, Antonella; Inesi, Achille; Zeuli, Errico; Journal of Chemical Research, Miniprint; nb. 3; (1990); p. 620 - 644 View in Reaxys

O HO

Rx-ID: 2055746 View in Reaxys 198/449 Yield 83 %

Conditions & References With dihydrogen peroxide, tungsten(VI) trioxide hydrate in acetonitrile, Time= 40h, T= 0 °C Jefford, Charles W.; Li, Yun; Jaber, Amer; Boukouvalas, John; Synthetic Communications; vol. 20; nb. 17; (1990); p. 2589 - 2596 View in Reaxys

Rx-ID: 2290452 View in Reaxys 199/449 Yield

Conditions & References With perchloric acid, acetaldehyde, acetone, sodium chloride in water, T= 25 °C , Irradiation, Rate constant, Equilibrium constant

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Keeffe; Kresge; Schepp; Journal of the American Chemical Society; vol. 112; nb. 12; (1990); p. 4862 - 4868 View in Reaxys With sulfuric acid in water, T= 25 °C , Rate constant, Equilibrium constant Dubois, Jaques-Emile; El-Alaoui, Mohiedine; Toullec, Jean; Journal of the American Chemical Society; vol. 103; nb. 18; (1981); p. 5393 - 5401 View in Reaxys in water, T= 25 °C , ionic strength: 0.01 M, Equilibrium constant Keeffe, J. R.; Kresge, A. J.; Schepp, N. P.; Journal of the American Chemical Society; vol. 110; nb. 6; (1988); p. 1993 - 1995 View in Reaxys

Rx-ID: 2409820 View in Reaxys 200/449 Yield

Conditions & References

74.9 % Chromat.

With Pd/SiO2 in N,N-dimethyl-formamide, Time= 24h, T= 59.9 °C , various solvents, various reagents, Product distribution Baba, T.; Nakano, K.; Nishiyama, S.; Tsurya, S.; Masai, M.; Journal of the Chemical Society, Chemical Communications; nb. 4; (1990); p. 348 - 349 View in Reaxys

74.9 % Chromat.

With palladium matal-containing silica-supported catalyst in ethylene glycol dimethyl ether, Time= 24h, T= 59.9 °C , Title compound not separated from byproducts Baba, T.; Nakano, K.; Nishiyama, S.; Tsurya, S.; Masai, M.; Journal of the Chemical Society, Chemical Communications; nb. 4; (1990); p. 348 - 349 View in Reaxys

Rx-ID: 2410039 View in Reaxys 201/449 Yield 90.1 %

Conditions & References With oxygen, palladium matal-containing silica-supported catalyst in various solvent(s), Time= 24h, T= 59.9 °C , Pd(0) supported on various zeolites , influence of calcination and reaction temperature and of the solvent, Product distribution, Mechanism Baba, Toshide; Nakano, Kaichiro; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 7; (1990); p. 1113 - 1119 View in Reaxys

90.1 %, 0.8 %

With oxygen, silica gel, palladium in various solvent(s), Time= 24h, T= 59.9 °C , solvent, Product distribution Baba; Nakano; Nishiyama; Tsuruya; Masai; Journal of the Chemical Society - Series Chemical Communications; nb. 22; (1989); p. 1697 - 1699 View in Reaxys

90.1 %

With oxygen, silica gel, palladium in various solvent(s), Time= 24h, T= 59.9 °C , Yields of byproduct given Baba, Toshide; Nakano, Kaichiro; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 7; (1990); p. 1113 - 1119 View in Reaxys

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0.8 %, 90.1 %

With oxygen, silica gel, palladium in various solvent(s), Time= 24h, T= 59.9 °C Baba; Nakano; Nishiyama; Tsuruya; Masai; Journal of the Chemical Society - Series Chemical Communications; nb. 22; (1989); p. 1697 - 1699 View in Reaxys

O O

Rx-ID: 2478468 View in Reaxys 202/449 Yield

Conditions & References With sulfuric acid in 1,4-dioxane, T= 25 °C , Equilibrium constant Antonovskii, V. L.; Fedorova, E. V.; Karamyan, S. H.; Ananchenko, S. N.; Doklady Chemistry; vol. 311; nb. 4; (1990); p. 75 - 78; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 311; nb. 6; (1990); p. 1377 - 1381 View in Reaxys

C4H7CHO (Pentenal), (C5H8O), H, OH

Rx-ID: 8426187 View in Reaxys 203/449 Yield

Conditions & References With O, p= 0.9 - 2.3Torr , Ambient temperature, Rate constant, Mechanism Heinemann-Fiedler, P.; Hoyermann, K.; Rohde, G.; Berichte der Bunsen-Gesellschaft; vol. 94; nb. 11; (1990); p. 1400 - 1404 View in Reaxys O O

O O

Rx-ID: 1598360 View in Reaxys 204/449 Yield

Conditions & References

57.5 %, 63.6 %

With water, sodium perchlorate, Ambient temperature, electrolysis Michida; Hatsumura; Sayo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3393 - 3395 View in Reaxys

57.5 %, 63.6 %

With water, sodium perchlorate, Ambient temperature, electrolysis, anodic oxidation of several o-nitrophenylthioiminocycloalkanes, Product distribution Michida; Hatsumura; Sayo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3393 - 3395 View in Reaxys

Rx-ID: 1817849 View in Reaxys 205/449 Yield

Conditions & References With hydrogen, Trimethylene glycol in tetrahydrofuran, Time= 0.5h, p= 760Torr , Ambient temperature, Yield given Machinaga, Nobuo; Kibayashi, Chihiro; Tetrahedron Letters; vol. 30; nb. 31; (1989); p. 4165 - 4168 View in Reaxys

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O O

Rx-ID: 1917527 View in Reaxys 206/449 Yield

Conditions & References

78 %

With Wilkinson's catalyst, ethene in chloroform, Time= 16h, T= 25 °C Campbell, Richard E.; Lochow, Charles F.; Vora, Krishnakant P.; Miller, Roy G.; Journal of the American Chemical Society; vol. 102; nb. 18; (1980); p. 5824 - 5830 View in Reaxys

78 %

With [(η2-cyclooctene)4Rh2(μ-Cl)2], trislt;p-(N,N-dimethylamino)phenylgt;phosphine in dichloromethane, Time= 120h, Ambient temperature, further reagents Larock,R.C.; Oertle,K.; Potter,G.F.; Journal of the American Chemical Society; vol. 102; (1980); p. 190 View in Reaxys With (PPh3)2Co(dppe) in acetonitrile, benzene, Time= 1h, T= 70 °C , Yield given Vinogradov, M. G.; Tuzikov, A. B.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 11.2; (1989); p. 2353 - 2356; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1989); p. 2565 - 2568 View in Reaxys O

Rx-ID: 1984099 View in Reaxys 207/449 Yield

Conditions & References

0.8 %, 87.4 %

N O

Rx-ID: 2125614 View in Reaxys 208/449 Yield

Conditions & References With oxygen, 1) CH2Cl2, -78 deg C, 40 min, irradiation; 2) CH2Cl2, -78 to -10 deg C, 20 min, irradiation, Yield given. Multistep reaction Majerski, Zdenko; Vinkovic, Vladimir; Synthesis; nb. 7; (1989); p. 559 - 560 View in Reaxys

Rx-ID: 2218925 View in Reaxys 209/449 Yield

Conditions & References With sulfuric acid in butan-1-ol, activation energy, Thermodynamic data Danilov, V. A.; Barysheva, N. A.; Postylyakov, A. B.; Rybina, E. A.; Sapozhnikov, Yu. E.; J. Appl. Chem. USSR (Engl. Transl.); vol. 62; nb. 1.2; (1989); p. 144 - 147,130 - 133 View in Reaxys

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O O

N O

S E N

N O

S O N O

Rx-ID: 3256487 View in Reaxys 210/449 Yield 11.3 %, 20.0 %, 26.7 %

Conditions & References With sodium perchlorate in acetonitrile, Ambient temperature, electrolysis Michida; Hatsumura; Sayo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3393 - 3395 View in Reaxys

O Br

Rx-ID: 3959822 View in Reaxys 211/449 Yield

Conditions & References With benzyltrimethylammonium tribromide, sodium acetate in water, acetic acid, Time= 1h, T= 60 °C Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo; Bulletin of the Chemical Society of Japan; vol. 62; nb. 8; (1989); p. 2585 - 2588 View in Reaxys O Br

potassium tetracarbonylferrate Rx-ID: 5929739 View in Reaxys 212/449

Yield 60 % Chromat.

Conditions & References in various solvent(s), Time= 24h, Ambient temperature Yamashita, Masakazu; Uchida, Masaya; Tashika, Haruyoshi; Suemitsu, Rikisaku; Bulletin of the Chemical Society of Japan; vol. 62; nb. 8; (1989); p. 2728 - 2729 View in Reaxys

S– K+

Rx-ID: 1977279 View in Reaxys 213/449 Yield

Conditions & References With lead(IV) acetate in benzene, T= 80 °C , Yield given. Yields of byproduct given Kapustina, N. I.; Popkov, A. Yu.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 37; (1988); p. 2289 - 2293; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1988); p. 2538 - 2542 View in Reaxys O

O O

Rx-ID: 2003321 View in Reaxys 214/449

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Yield

Conditions & References

65 % Turn- With lead(IV) acetate, copper(II) oxide in benzene, Time= 3.5h, T= 80 °C , further Cu(II) reagents ov., 12 % Kapustina, N. I.; Popkov, A. Yu.; Gasanov, R. G.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the Turnov. USSR, Division of Chemical Science (English Translation); vol. 37; nb. 10; (1988); p. 2095 - 2099; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1988); p. 2327 - 2331 View in Reaxys 7 % Turnov., 81 % Turnov.

With lead(IV) acetate, copper diacetate in benzene, Time= 3.5h, T= 80 °C , further Cu(II) reagents Kapustina, N. I.; Popkov, A. Yu.; Gasanov, R. G.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 37; nb. 10; (1988); p. 2095 - 2099; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1988); p. 2327 - 2331 View in Reaxys

O O

Rx-ID: 2003322 View in Reaxys 215/449 Yield

Conditions & References With lead(IV) acetate, potassium bromide in benzene, T= 80 °C , Yield given. Yields of byproduct given Kapustina, N. I.; Popkov, A. Yu.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 37; (1988); p. 2289 - 2293; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1988); p. 2538 - 2542 View in Reaxys

O NH

Rx-ID: 2526698 View in Reaxys 216/449 Yield

Conditions & References With n-butyllithium, air, zinc dibromide, 1) THF, hexane, -78 deg C, 30 min., 2) -20 deg C, 30 min., Yield given. Multistep reaction Chen, Huai Gu; Knochel, Paul; Tetrahedron Letters; vol. 29; nb. 51; (1988); p. 6701 - 6702 View in Reaxys multistep reaction; in the presence or in the absence of ZnBr2, Product distribution Chen, Huai Gu; Knochel, Paul; Tetrahedron Letters; vol. 29; nb. 51; (1988); p. 6701 - 6702 View in Reaxys

O S

Rx-ID: 2847972 View in Reaxys 217/449 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

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O O

Rx-ID: 2943396 View in Reaxys 218/449 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

O NH

Rx-ID: 2951249 View in Reaxys 219/449 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 O

Rx-ID: 3946286 View in Reaxys 220/449 Yield

Conditions & References

86 % Chromat.

With 2,2'-azo-bisisobutyronitrile, tri-n-butyl-tin hydride, Time= 6h, T= 60 °C Shibata, Ikuya; Suzuki, Taro; Baba, Akio; Matsuda, Haruo; Journal of the Chemical Society, Chemical Communications; nb. 13; (1988); p. 882 - 883 View in Reaxys

Rx-ID: 3946287 View in Reaxys 221/449 Yield

Conditions & References With N,N,N',N',N'',N''-hexamethylphosphoric triamide, tri-n-butyl-tin hydride, Time= 1h, T= 60 °C , Yield given. Yields of byproduct given Shibata, Ikuya; Suzuki, Taro; Baba, Akio; Matsuda, Haruo; Journal of the Chemical Society, Chemical Communications; nb. 13; (1988); p. 882 - 883 View in Reaxys

Rx-ID: 2055966 View in Reaxys 222/449 Yield 90 %

Conditions & References With silica gel, iron(III) chloride, Time= 0.333333h, T= 20 °C

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Fadel, Antoine; Yefsah, Ramdane; Salauen, Jacques; Synthesis; nb. 1; (1987); p. 37 - 40 View in Reaxys With sulfuric acid in water, T= 25 °C , Rate constant Dubois, Jaques-Emile; El-Alaoui, Mohiedine; Toullec, Jean; Journal of the American Chemical Society; vol. 103; nb. 18; (1981); p. 5393 - 5401 View in Reaxys

O O

Rx-ID: 2536982 View in Reaxys 223/449 Yield

Conditions & References

7 % Chromat., 93 % Chromat.

With dihydridotetrakis(triphenylphosphine)ruthenium(II) in benzene, T= 80 °C , Heating Minami, Ichiro; Tsuji, Jiro; Tetrahedron; vol. 43; nb. 17; (1987); p. 3903 - 3916 View in Reaxys

O O

Rx-ID: 2536983 View in Reaxys 224/449 Yield

Conditions & References

7 % Chromat., 4 % Chromat., 89 % Chromat.

With Pd(OAc)2*PPh3 in acetonitrile, T= 80 °C , Heating

7 % Chromat., 89 % Chromat., 4 % Chromat.

With Pd(OAc)2*PPh3 in acetonitrile, T= 80 °C , Heating, other catalysts and solvents, Product distribution

Minami, Ichiro; Tsuji, Jiro; Tetrahedron; vol. 43; nb. 17; (1987); p. 3903 - 3916 View in Reaxys

Minami, Ichiro; Tsuji, Jiro; Tetrahedron; vol. 43; nb. 17; (1987); p. 3903 - 3916 View in Reaxys With palladium diacetate, triphenylphosphine in acetonitrile, Time= 4h, T= 80 °C , further catalysts, solvents, temperature and reaction time, Product distribution Minami, Ichiro; Shimizu, Isao; Tsuji, Jiro; Journal of Organometallic Chemistry; vol. 296; (1985); p. 269 - 280 View in Reaxys

O O

Rx-ID: 2541290 View in Reaxys 225/449 Yield 71 %

Conditions & References With palladium diacetate, triphenylphosphine in acetonitrile, Time= 1.5h, Heating, Yields of byproduct given Minami, Ichiro; Nisar, Mohammad; Yuhara, Masami; Shimizu, Isao; Tsuji, Jiro; Synthesis; nb. 11; (1987); p. 992 - 998

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View in Reaxys

N+

I–

O I–

Rx-ID: 2630203 View in Reaxys 226/449 Yield

Conditions & References

71 %

With sodium hydroxide in ethanol, T= 25 °C Katritzky, Alan R.; Fan, Wei-Qiang; Li, Qiao-Ling; Tetrahedron Letters; vol. 28; nb. 11; (1987); p. 1195 - 1198 View in Reaxys

71 %

With sodium hydroxide in ethanol, T= 25 °C , Product distribution Katritzky, Alan R.; Fan, Wei-Qiang; Li, Qiao-Ling; Tetrahedron Letters; vol. 28; nb. 11; (1987); p. 1195 - 1198 View in Reaxys

O O

N O

Rx-ID: 21565924 View in Reaxys 227/449 Yield

Conditions & References Reaction Steps: 2 1: 70 percent / acetone / 25 °C 2: 71 percent / NaOH / aq. ethanol / 25 °C With sodium hydroxide in ethanol, acetone Katritzky, Alan R.; Fan, Wei-Qiang; Li, Qiao-Ling; Tetrahedron Letters; vol. 28; nb. 11; (1987); p. 1195 - 1198 View in Reaxys

F F

O F

O– F O F

–O

O Na +

F F

O F

F F

(v1)

O O F

Na +

F F F

N F

F F

N F

FO F (v1)

F F F

Rx-ID: 1869954 View in Reaxys 228/449 Yield

Conditions & References in 1,2,2-trifluoro-trichloroethane, T= 20 °C Zhao, Cheng-Xue; Jiang, Xi-Kui; Chen, Guo-Fei; Qu, Yan-Ling; Wang, Xian-Shan; Lu, Jian-Ying; Journal of the American Chemical Society; vol. 108; nb. 11; (1986); p. 3132 - 3133 View in Reaxys O Br

Rx-ID: 1935094 View in Reaxys 229/449 Yield

Conditions & References With lt;(1R,4R,8S,11S)-1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecanegt;nickel, water, T= 25 °C , Yield given

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Bakac, Andreja; Espenson, James H.; Journal of the American Chemical Society; vol. 108; nb. 17; (1986); p. 5353 - 5354 View in Reaxys O

NH N

HN O

NH N

N H

O O

Rx-ID: 2003270 View in Reaxys 230/449 Yield 10.3 %

Conditions & References Time= 25h, T= 115 °C , autorecycling oxidation, other 10- and 3,10-substituted 8-methylpyrido<2,3-d:6,5-d'>dipyrimidine-2,4,6(3H,10H,7H)-triones, Product distribution Moriyama, Kenji; Nagamatsu, Tomohisa; Yoneda, Fumio; Journal of Heterocyclic Chemistry; vol. 23; (1986); p. 241 - 243 View in Reaxys

10.3 %

in neat (no solvent), Time= 25h, T= 115 °C , autorecycling oxidation, Product distribution Moriyama, Kenji; Nagamatsu, Tomohisa; Yoneda, Fumio; Journal of Heterocyclic Chemistry; vol. 23; (1986); p. 241 - 243 View in Reaxys O

HN N

O N

HN O

N N

N H

O O

Rx-ID: 2003272 View in Reaxys 231/449 Yield 9.0 %

Conditions & References Time= 25h, T= 115 °C , autorecycling oxidation, Product distribution Moriyama, Kenji; Nagamatsu, Tomohisa; Yoneda, Fumio; Journal of Heterocyclic Chemistry; vol. 23; (1986); p. 241 - 243 View in Reaxys O

O N

HN O

N N

N H

O O

Rx-ID: 2003273 View in Reaxys 232/449 Yield 8.7 %

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O N

HN O

N N

N H

O O

Rx-ID: 2003274 View in Reaxys 233/449 Yield 9.8 %

NH N

HN O

NH N

N H

Rx-ID: 2003275 View in Reaxys 234/449 Yield 12.7 %

O N

H N

O N

Rx-ID: 2003276 View in Reaxys 235/449 Yield 23.7 %

O N

N H

Rx-ID: 2003277 View in Reaxys 236/449 Yield 12.5 %

Conditions & References Time= 25h, T= 115 °C , autorecycling oxidation, Product distribution

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Moriyama, Kenji; Nagamatsu, Tomohisa; Yoneda, Fumio; Journal of Heterocyclic Chemistry; vol. 23; (1986); p. 241 - 243 View in Reaxys

N O

H N

O N

Rx-ID: 2003278 View in Reaxys 237/449 Yield 14.1 %

N O

H N

O N

Rx-ID: 2003279 View in Reaxys 238/449 Yield 11.5 %

NH N

HN O

NH N

N H

Rx-ID: 2003280 View in Reaxys 239/449 Yield 13.2 %

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O N

H N

O N

Rx-ID: 2003281 View in Reaxys 240/449 Yield 10.7 %

O N

HN O

N N

N H

Rx-ID: 2003282 View in Reaxys 241/449 Yield 14.1 %

O N

HN O

N N

N H

Rx-ID: 2003283 View in Reaxys 242/449 Yield 12.0 %

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O NH

HN O

NH N

N H

Rx-ID: 2003284 View in Reaxys 243/449 Yield

Conditions & References

8.5 %

Time= 25h, T= 115 °C , autorecycling oxidation, Product distribution Moriyama, Kenji; Nagamatsu, Tomohisa; Yoneda, Fumio; Journal of Heterocyclic Chemistry; vol. 23; (1986); p. 241 - 243 View in Reaxys O

O N

HN O

N N

N H

Rx-ID: 2003285 View in Reaxys 244/449 Yield

Conditions & References

8.4 %

O O

Rx-ID: 2008016 View in Reaxys 245/449 Yield 78 %

Conditions & References With boron trifluoride diethyl etherate, tetraethylammonium iodide in chloroform, Time= 4h, Heating Mandal, Arun K.; Shrotri, P. Y.; Ghogare, A. D.; Synthesis; nb. 3; (1986); p. 221 - 222 View in Reaxys

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F F

O O

F F F F F F

F F F F

–O

O F

F F

Na +

F F

Na + O–

(v1)

F F N

F F

(v1)

Rx-ID: 2246233 View in Reaxys 246/449 Yield

Cl O

Rx-ID: 2531176 View in Reaxys 247/449 Yield

Conditions & References With titanium tetrachloride Hatanaka, Yasuo; Kuwajima, Isao; Tetrahedron Letters; vol. 27; nb. 6; (1986); p. 719 - 722 View in Reaxys

–O

F F

Na + F

F O

F F

F O

F F

F F O–

F F

Na +

(v1)

F N

F F F

(v1)

Rx-ID: 2626690 View in Reaxys 248/449 Yield

(v4)

Ni +

(v4)

(v5) (v4) (v4)

(v4)

(v4) N (v4) 2+

(v4)

Rx-ID: 26855472 View in Reaxys 249/449 Yield

Conditions & References With water in water, Kinetics, byproducts: NH3, OH(1-); 25°C, pH 12;; not sepd., detected by UV spectra; Bakac, Andreja; Espenson, James H.; Journal of the American Chemical Society; vol. 108; nb. 17; (1986); p. 5353 - 5354 ; (from Gmelin)

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View in Reaxys

Rx-ID: 1917529 View in Reaxys 250/449 Yield

Conditions & References With N-dodecane, Co(N2)(PPh3)3H in benzene, T= 20 °C , influence of catalyst employed, temperature and time effects; further catalysts; further temperature, Product distribution Vinogradov, M. G.; Tuzikov, A. B.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; nb. 2; (1985); p. 325 - 329; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1985); p. 356 - 361 View in Reaxys O

O O

Rx-ID: 1917530 View in Reaxys 251/449 Yield

Conditions & References With C108H90Co2N2P6, 1,2-bis-(diphenylphosphino)ethane in benzene, Time= 1h, T= 70 °C , nature of the ligand, solvent and temperature dependence, Product distribution, Mechanism Vinogradov, M. G.; Tuzikov, A. B.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; nb. 11; (1985); p. 2369 - 2374; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1985); p. 2557 - 2562 View in Reaxys

O O

I HO

Rx-ID: 1945855 View in Reaxys 252/449 Yield

Conditions & References With n-butyllithium, chloro-trimethyl-silane, water, -110 deg C, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys O

Rx-ID: 2154460 View in Reaxys 253/449 Yield

Conditions & References With hydroxide in 1,4-dioxane, water, T= 25.1 °C , Rate constant Elvidge, John A.; Jones, John R.; Russell, Jeremy C.; Wiseman, Alan; Coombs, Maurice M.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1985); p. 563 - 566 View in Reaxys

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O S

Rx-ID: 2482581 View in Reaxys 254/449 Yield

Conditions & References With hydrogenchloride in methanol, Time= 5h, 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

O I

N O

Rx-ID: 2533124 View in Reaxys 255/449 Yield

Conditions & References

71 % Chromat.

With n-butyllithium in tetrahydrofuran, T= -78 °C Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys

NH H N

O N

Rx-ID: 2591967 View in Reaxys 256/449 Yield

Conditions & References With hydrogenchloride in chloroform, Time= 5h, T= 23 °C , Product distribution Bobowski; Shavel Jr.; Journal of Heterocyclic Chemistry; vol. 22; nb. 6; (1985); p. 1679 - 1688 View in Reaxys

O O

Rx-ID: 3531693 View in Reaxys 257/449 Yield

Conditions & References With oxygen, p-benozquinone, palladium dichloride in ethanol, Time= 8h, T= 30 °C , p= 860Torr , Product distribution Takehira, Katsuomi; Hayakawa, Takashi; Orita, Hideo; Chemistry Letters; (1985); p. 1835 - 1838 View in Reaxys

OH O

O O

Rx-ID: 3959818 View in Reaxys 258/449

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Yield

Conditions & References

10 %, 54 %

With dihydridotetrakis(triphenylphosphine)ruthenium(II) in benzene, Time= 22h, T= 100 °C Minami, Ichiro; Shimizu, Isao; Tsuji, Jiro; Journal of Organometallic Chemistry; vol. 296; (1985); p. 269 - 280 View in Reaxys

O Cl

Rx-ID: 1657247 View in Reaxys 259/449 Yield

Conditions & References

2.2 g, 12.5 %

in acetonitrile, Time= 21h, Heating Lochead, Alistair W.; Proctor, George R.; Caton, Michael P. L.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1984); p. 2477 - 2489 View in Reaxys OH +

O O+

Rx-ID: 1906354 View in Reaxys 260/449 Yield

Conditions & References Gas phase. Determ. by ICR spect., Equilibrium constant, Thermodynamic data Bouchoux, G.; Houriet, R.; Tetrahedron Letters; vol. 25; nb. 50; (1984); p. 5755 - 5758 View in Reaxys

(v1)

OH O

O O

Rx-ID: 1978586 View in Reaxys 261/449 Yield

Conditions & References With oxygen, Nitrous oxide in water, Irradiation, pH=6.5, Rate constant, Mechanism Zegota, Henryk; Schuchmann, Man Nien; von Sonntag, Clemens; Journal of Physical Chemistry; vol. 88; nb. 23; (1984); p. 5589 - 5593 View in Reaxys OH O

O O

Rx-ID: 1999264 View in Reaxys 262/449 Yield

Conditions & References With oxygen, Nitrous oxide in water, Irradiation, pH=6.5, Product distribution Zegota, Henryk; Schuchmann, Man Nien; von Sonntag, Clemens; Journal of Physical Chemistry; vol. 88; nb. 23; (1984); p. 5589 - 5593 View in Reaxys

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OH O

Rx-ID: 2003317 View in Reaxys 263/449 Yield

Conditions & References

10 % Turnov., 59 % Turnov., 2 % Turnov., 5 % Turnov., 2 % Turnov.

With pyridine, lead(IV) acetate, copper diacetate in benzene, T= 80 °C , other ratio of cyclopentanol : LTACu(OAc)2, Product distribution Nikishin, G. I.; Kapustina, N. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 6; (1984); p. 1235 - 1239; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 6; (1984); p. 1345 - 1348 View in Reaxys

O O

Cl O

Rx-ID: 2003318 View in Reaxys 264/449 Yield

Conditions & References

8 % Turnov., 2 % Turnov., 3 % Turnov., 80 % Turnov.

With pyridine, lead(IV) acetate, lithium chloride in benzene, Time= 0.25h, T= 65 - 70 °C , Further byproducts given Nikishin, G. I.; Kapustina, N. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 6; (1984); p. 1235 - 1239; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 6; (1984); p. 1345 - 1348 View in Reaxys

O O

Cl O

Rx-ID: 2003319 View in Reaxys 265/449 Yield

Conditions & References

8 % Turnov., 3 % Turnov., 3 % Turnov., 80 % Turnov.

O O

Rx-ID: 2054942 View in Reaxys 266/449 Yield 0.25 % Turnov., 91.0 % Turnov.

Conditions & References With pyridine, lead(IV) acetate, copper diacetate in benzene, Time= 2h, T= 80 °C Kapustina, N. I.; Spektor, S. S.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 12; (1984); p. 2490 - 2497; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1984); p. 2721 - 2729 View in Reaxys

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O HO O

Rx-ID: 2055083 View in Reaxys 267/449 Yield

Conditions & References

0.60 % Turnov., 94.0 % Turnov.

With pyridine, lead(IV) acetate, copper diacetate in benzene, Time= 2h, T= 80 °C Kapustina, N. I.; Spektor, S. S.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 12; (1984); p. 2490 - 2497; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1984); p. 2721 - 2729 View in Reaxys

O N

Rx-ID: 2104493 View in Reaxys 268/449 Yield

Conditions & References With oxygen, methylene blue in dichloromethane, Time= 5h, T= 15 °C , Irradiation Ando, Wataru; Sato, Rikiya; Sonobe, Hideki; Akasaka, Takeshi; Tetrahedron Letters; vol. 25; nb. 8; (1984); p. 853 - 856 View in Reaxys O S

Rx-ID: 2147523 View in Reaxys 269/449 Yield

Conditions & References With sulfuric acid in ethanol, Time= 15h, Ambient temperature Ogura, K.; Yamashita, M.; Suzuki, M.; Furukawa, S.; Tsuchinashi, G.; Bulletin of the Chemical Society of Japan; vol. 57; nb. 6; (1984); p. 1637 - 1642 View in Reaxys

O HO

Rx-ID: 2147617 View in Reaxys 270/449 Yield 19.0 % Turnov., 71.5 % Turnov.

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Rx-ID: 2149337 View in Reaxys 271/449 Yield

Conditions & References

0.30 % Turnov., 97.0 % Turnov.

O HO

Rx-ID: 2188513 View in Reaxys 272/449 Yield

Conditions & References

8.5 % Turnov., 85.5 % Turnov.

Rx-ID: 2409818 View in Reaxys 273/449 Yield

Conditions & References

15 % Chromat., 72 % Chromat., 16 % Chromat.

bution Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao; Kataoka, Hideaki; Chemistry Letters; (1984); p. 1133 - 1136 View in Reaxys

O O

With [Pd(1,2-bis(diphenylphosphino)ethane)(OAc)2] in acetonitrile, T= 80 °C , var. catalyst, solvent;, Product distri-

Rx-ID: 2536981 View in Reaxys 274/449 Yield 76 % Chromat.

Conditions & References With palladium diacetate in acetonitrile, Time= 2h, T= 80 °C Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao; Tetrahedron Letters; vol. 25; nb. 26; (1984); p. 2791 - 2792 View in Reaxys

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OH +

O HO

C+

Rx-ID: 3740570 View in Reaxys 275/449 Yield

<Ru(CO)2CH2(PMe2Ph)2> Rx-ID: 5929734 View in Reaxys 276/449

Yield

Conditions & References in various solvent(s), T= -50.1 °C Saunders, David R.; Mawby, Roger J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1984); p. 2133 - 2136 View in Reaxys

S Br

O S

Rx-ID: 1543872 View in Reaxys 277/449 Yield

Conditions & References With hydrogenchloride, Aliquatreg; 336, 1.) toluene, 50 percent NaOH, 60 deg C; 2.) methanol, reflux, Yield given. Multistep reaction Ogura, Katsuyuki; Yahata, Nobuhiro; Hashizume, Kimitoshi; Tsuyama, Koichi; Takahashi, Kazumasa; Iida, Hirotada; Chemistry Letters; (1983); p. 767 - 770 View in Reaxys

Rx-ID: 1698894 View in Reaxys 278/449 Yield

Conditions & References With trans-Mo(N2)2(1,2-bis(diphenylphosphino)ethane)2 in benzene, Time= 3h, Heating, other acyclic and cyclic allylic alcohols, Product distribution, Mechanism Lin, Yingrui; Lu, Xiyan; Journal of Organometallic Chemistry; vol. 251; nb. 3; (1983); p. 321 - 326 View in Reaxys OH

O O

OH O

Rx-ID: 1917531 View in Reaxys 279/449 Yield

Conditions & References

38 % Turn- With cobalt in tetrahydrofuran, Time= 2h, T= 20 °C , other reagent, Product distribution ov.

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Vinogradov, M. G.; Tuzikov, A. B.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 32; (1983); p. 1535; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1983); p. 1686 - 1687 View in Reaxys

O O

Rx-ID: 2140361 View in Reaxys 280/449 Yield

Conditions & References With air in various solvent(s), T= 160 °C , p= 760Torr , Yield given. Yields of byproduct given Druliner, J. D.; Kitson, F. G.; Rudat, M. A.; Tolman, C. A.; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4951 - 4953 View in Reaxys

OH O

Rx-ID: 2140362 View in Reaxys 281/449 Yield

Conditions & References With air in various solvent(s), T= 160 °C , p= 760Torr , var. cond., var. solv.; deuter. comp., Product distribution, Mechanism Druliner, J. D.; Kitson, F. G.; Rudat, M. A.; Tolman, C. A.; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4951 - 4953 View in Reaxys

OH O

H N O N

Rx-ID: 3120589 View in Reaxys 282/449 Yield

Conditions & References With soda-lime McHintosh, John M.; Pillon, Lilianna Z.; Acquaah, Samuel O.; Green, James R.; White, Graham S.; Canadian Journal of Chemistry; vol. 61; (1983); p. 2016 - 2021 View in Reaxys

O O

CO2 Rx-ID: 7452267 View in Reaxys 283/449

Yield

Conditions & References

32 % Turn- T= 270 °C , other temperature, Product distribution ov., 11 % Turnov., 29 Galoci, Jan; Prochazka, Milos; Klinotova, Eva; Collection of Czechoslovak Chemical Communications; vol. 48; % Turnov., nb. l; (1983); p. 1729 - 1733

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11 % Turn- View in Reaxys ov. O HO

O O

Rx-ID: 25059834 View in Reaxys 284/449 Yield

Conditions & References 13 : EXAMPLE 13 EXAMPLE 13 As described in Example 12(a), 2-[4-(2-oxopentylidenemethyl)phenyl]propionic acid, m.p. 158°, is obtained from cyclopentanone and 2-(4-formylphenyl)propionic acid. Patent; Schering Aktiengesellschaft; US4407823; (1983); (A1) English View in Reaxys

(v3)

(v5)

(v3)

(v5) (v12)

(v3)

O (v5)

(v5)

(v3)

(v9) (v9)

(v5) (v5)

O (v5)

(v5) (v5)

(v5)

(v3)

(v5)

Rx-ID: 26854153 View in Reaxys 285/449 Yield 83 %, 90 %

Conditions & References With CO in toluene, toluene soln. of Mo complex placed in autoclave under 50 atm CO pressure, stirred at 90°C for 12 h; distn., trapping at -78°C Diversi, Pietro; Ingrosso, Giovanni; Lucherini, Antonio; Porzio, William; Zocchi, Marcello; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1983); p. 967 - 974 ; (from Gmelin) View in Reaxys O

Rx-ID: 1507406 View in Reaxys 286/449 Yield

Conditions & References T= 500 - 590 °C , thermal transformation Karakhanov, E. A.; Karzhavina, N. P.; Brezhnev, L. Yu.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 1; (1982); p. 191 - 192; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1982); p. 203 - 204 View in Reaxys

Rx-ID: 1514376 View in Reaxys 287/449 Yield

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S S

Rx-ID: 1516212 View in Reaxys 288/449 Yield

Conditions & References

80 %

With trimethylsilyl bromide, dimethyl sulfoxide in tetrachloromethane, Time= 24h, T= 75 - 80 °C Olah, George A.; Narang, Subbash C.; Mehrotra, Ashok K.; Synthesis; nb. 11; (1982); p. 965 - 966 View in Reaxys O

Rx-ID: 1917528 View in Reaxys 289/449 Yield

Conditions & References With RhCl(PMe3)3, Time= 2h, T= 50 °C , Yield given. Yields of byproduct given Milstein, David; Journal of the Chemical Society, Chemical Communications; nb. 23; (1982); p. 1357 - 1358 View in Reaxys With RhCl(PMe3)3, Time= 2h, T= 50 °C , Product distribution, Mechanism Milstein, David; Journal of the Chemical Society, Chemical Communications; nb. 23; (1982); p. 1357 - 1358 View in Reaxys F

S O

Rx-ID: 2108317 View in Reaxys 290/449 Yield

Conditions & References

10 %

in ethanol, water, Time= 168h, T= 160 °C , 50percent CF3CH2OH, NEt4Br, Mechanism Hanack, Michael; Maerkl, Rainer; Martinez, Antonio Garcia; Chemische Berichte; vol. 115; nb. 2; (1982); p. 772 782 View in Reaxys With lutidine, water in ethanol, T= 151 - 176.5 °C , Kinetics Pfeifer,W.D. et al.; Journal of the American Chemical Society; vol. 93; nb. 6; (1971); p. 1513 - 1516 View in Reaxys O

O O

Rx-ID: 2409984 View in Reaxys 291/449 Yield

Conditions & References

43 % Chromat., 12 % Chromat.

With antimony(III) chloride in dichloromethane, Time= 1h, T= 0 °C Tirpak, Robin E.; Rathke, Michael W.; Journal of Organic Chemistry; vol. 47; nb. 26; (1982); p. 5099 - 5102 View in Reaxys

O S

O S O

Rx-ID: 2819523 View in Reaxys 292/449

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Yield 94 %

Conditions & References With hydrogenchloride in methanol, Time= 3h, Heating Ogura, Katsuyuki; Suzuki, Michiyo; Watanabe, Jun-ichi; Yamashita, Mitsuo; Iida, Hirotada; Tsuchihashi, Genichi; Chemistry Letters; (1982); p. 813 - 814 View in Reaxys OH

Rx-ID: 3531639 View in Reaxys 293/449 Yield 4 % Chromat., 3 % Chromat., 27 % Chromat., 1 % Chromat.

Conditions & References With Pd(NO2)Cl(MeCN)2 in dichloromethane, Time= 6h, T= 20 °C , other cycloalkenes, Product distribution Andrews,M.A.; Cheng,C.W.; Journal of the American Chemical Society; vol. 104; (1982); p. 4268 View in Reaxys

O HO

condensation products

OH O

Rx-ID: 6727465 View in Reaxys 294/449 Yield

Conditions & References With carbon dioxide, zinc oxide, multistep reaction, Product distribution Vasina, T. V.; Chelmakova, S. A.; Lutovinova, V. N.; Liberman, A. L.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 10; (1982); p. 2046 - 2048; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1982); p. 2325 - 2327 View in Reaxys O O

Rx-ID: 25041128 View in Reaxys 295/449 Yield

Conditions & References II.C : EXAMPLE II-C STR37 EXAMPLE II-C STR37 Into a 250 ml reaction flask equipped with mechanical stirrer, immersion thermometer, water-cooled condenser and heating mantle is placed 38.73 grams (0.23 moles) of the aldol condensation product of cyclopentanone and n-valeraldehyde produced according to Example II-A and 176.4 ml of 5percent hydrogen chloride in n-butanol (8.4 ml of 38percent HCl in 168 ml n-butanol). The reaction mass is heated with stirring to reflux and refluxed until the ratio of endo:exo isomer is 13:1 (87.4percent endo:6.7percent exo) monitored on a 6'*1/4" SE-30 glass packed GLC column). The time of reaction is 165 minutes. At the end of the 165-minute period the reaction apparatus is shut down and the reaction mass is washed with 1 volume of saturated sodium chloride solution followed by 1 volume of 10percent sodium carbonate solution and 3 volumes of saturated sodium chloride solution. The product is then dried over anhydrous sodium sulfate to yield 249 grams of crude. The crude material is distilled under vacuum over a rush-over head as follows: Yield of product is 17.66 grams (50.52percent). With hydrogenchloride, sodium chloride, sodium carbonate in butan-1-ol Patent; International Flavors and Fragrances Inc.; US4260830; (1981); (A1) English View in Reaxys II.C : EXAMPLE II-C STR57 EXAMPLE II-C STR57

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Into a 250 ml reaction flask equipped with mechanical stirrer, immersion thermometer, water-cooled condenser and heating mantle is placed 38.73 grams (0.23 moles) of the aldol condensation product of cyclopentanone and n-valeraldehyde produced according to Example II-A and 176.4 ml of 5percent hydrogen chloride in n-butanol (8.4 ml of 38percent HCl in 168 ml n-butanol). The reaction mass is heated with stirring to reflux and refluxed until the ratio of endo:exo isomer is 13:1 (87.4percent endo:6.7percent exo) monitored on a 6'*1/4" SE-30 glass packed GLC column). The time of reaction is 165 minutes. At the end of the 165-minute period the reaction apparatus is shut down and the reaction mass is washed with 1 volume of saturated sodium chloride solution followed by 1 volume of 10percent sodium carbonate solution and 3 volumes of saturated sodium chloride solution. The product is then dried over anhydrous sodium sulfate to yield 249 grams of crude. The crude material is distilled under vacuum over a rush-over head as follows: Yield of product is 17.66 grams (50.52percent). With hydrogenchloride, sodium chloride, sodium carbonate in butan-1-ol Patent; International Flavors and Fragrances Inc.; US4310701; (1982); (A1) English View in Reaxys

H O+

OH +

Rx-ID: 1480640 View in Reaxys 296/449 Yield

Conditions & References T= 24.9 °C , ΔG0, Thermodynamic data Bromilow, J.; Abboud, J. L. M.; Lebrilla, C. B.; Taft, R. W.; Scorrano, G.; Lucchini V.; Journal of the American Chemical Society; vol. 103; nb. 18; (1981); p. 5448 - 5453 View in Reaxys H O+

OH +

Rx-ID: 1480652 View in Reaxys 297/449 Yield

O H

Rx-ID: 1999266 View in Reaxys 298/449 Yield 44 %, 12 %, 9.0 %, 3.5 %, 1.5 %

Conditions & References With water, nitrogen(II) oxide, Time= 7.96667h, Irradiation, further reaction times, initial conc.,, Product distribution Takagi, H.; Washida, N.; Banbow, H.; Akimoto, H.; Okuda, M.; Journal of Physical Chemistry; vol. 85; nb. 18; (1981); p. 2701 - 2705 View in Reaxys OH

Rx-ID: 2055578 View in Reaxys 299/449

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Yield

Conditions & References

83.1 % Chromat., 0.5 % Chromat.

With sodium hydroxide, 9-borabicyclo[3.3.1]nonane dimer, dihydrogen peroxide, 1) THF, 65 deg C, 24 h, Product distribution Brown, Herbert C.; Chen, Jackson C.; Journal of Organic Chemistry; vol. 46; nb. 20; (1981); p. 3978 - 3988 View in Reaxys

O OH

Rx-ID: 2056254 View in Reaxys 300/449 Yield

Conditions & References

82.2 % Chromat., 2 % Chromat.

With sodium hydroxide, 9-borabicyclo[3.3.1]nonane dimer, dihydrogen peroxide, 1) THF, 25 deg C, 1.5 h, Product distribution Brown, Herbert C.; Chen, Jackson C.; Journal of Organic Chemistry; vol. 46; nb. 20; (1981); p. 3978 - 3988 View in Reaxys

Rx-ID: 2149740 View in Reaxys 301/449 Yield

Conditions & References

91.6 %

With hydrogenchloride, dihydrogen peroxide in acetonitrile, Time= 3h, T= 50 °C , the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C Rao, Darvasula V.; Stuber, Fred A.; Tetrahedron Letters; vol. 22; nb. 25; (1981); p. 2337 - 2340 View in Reaxys N

Rx-ID: 2163692 View in Reaxys 302/449 Yield

Conditions & References

22 % Turn- With sodium peroxodisulphate, silver nitrate in water, Time= 3h, T= 60 °C ov., 58 % Ogibin, Yu. N.; Velibekova, D. S.; Katsin, M. I.; Troyanskii, E. I.; Nikishin, G. I.; Bulletin of the Academy of ScienTurnov. ces of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 12; (1981); p. 2293 - 2298; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1981); p. 2755 - 2761 View in Reaxys

O O

S O

OH racemate

Rx-ID: 2200077 View in Reaxys 303/449 Yield

Conditions & References With sodium acetate (buffer) in acetic acid Wistuba, Eckehardt; Ruechardt, Christoph; Tetrahedron Letters; vol. 22; nb. 41; (1981); p. 4069 - 4072 View in Reaxys in acetic acid, rate constant: 171.4E5, Rate constant

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Wistuba, Eckehardt; Ruechardt, Christoph; Tetrahedron Letters; vol. 22; nb. 41; (1981); p. 4069 - 4072 View in Reaxys

OH HO

Rx-ID: 2537155 View in Reaxys 304/449 Yield

Conditions & References

70.3 %

OH HO

Rx-ID: 2538740 View in Reaxys 305/449 Yield

Conditions & References

60 %

Rx-ID: 3382729 View in Reaxys 306/449 Yield

Conditions & References With potassium hydroxide, Ru(O2CCF3)2(CO)(PPh3)2, 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= 4h, 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= 5h, T= 140 °C , Equilibrium constant, Rate constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys O

OH O

OH OH

Rx-ID: 3804869 View in Reaxys 307/449

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Yield

Conditions & References

46 % Chromat., 11.6 % Chromat., 2.1 % Chromat., 7 % Chromat.

With sodium hydroxide, 9-borabicyclo[3.3.1]nonane dimer, dihydrogen peroxide, 1) CCl4, 25 deg C, 22 h, Product distribution Brown, Herbert C.; Chen, Jackson C.; Journal of Organic Chemistry; vol. 46; nb. 20; (1981); p. 3978 - 3988 View in Reaxys

O Br

Rx-ID: 3927606 View in Reaxys 308/449 Yield

Conditions & References

85 %

With trimethylsilyl iodide in chloroform, Ambient temperature, or reflux Ho, Tse-Lok; Synthetic Communications; vol. 11; nb. 2; (1981); p. 101 - 104 View in Reaxys

Rx-ID: 21440830 View in Reaxys 309/449 Yield

Conditions & References Reaction Steps: 2 1: 90.6 percent / PdCl2(PhCN)2 / benzene / 2 h / Heating 2: 30percent H2O2, conc. HCl / acetonitrile / 3 h / 50 °C / the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C With hydrogenchloride, dihydrogen peroxide, bis(benzonitrile)palladium(II) dichloride in acetonitrile, benzene Rao, Darvasula V.; Stuber, Fred A.; Tetrahedron Letters; vol. 22; nb. 25; (1981); p. 2337 - 2340 View in Reaxys

O O

Rx-ID: 21440837 View in Reaxys 310/449 Yield

Conditions & References Reaction Steps: 3 1: 80 percent / 85percent phosphoric acid / 4 h / Ambient temperature 2: 100 percent / PdCl2(PhCN)2 / benzene / 2 h / Heating 3: 30percent H2O2, conc. HCl / acetonitrile / 3 h / 50 °C / the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C With hydrogenchloride, phosphoric acid, dihydrogen peroxide, bis(benzonitrile)palladium(II) dichloride in acetonitrile, benzene Rao, Darvasula V.; Stuber, Fred A.; Tetrahedron Letters; vol. 22; nb. 25; (1981); p. 2337 - 2340 View in Reaxys Reaction Steps: 3 1: 80 percent / 85percent phosphoric acid / 4 h / Ambient temperature 2: 92 percent / PdCl2(PhCN)2 / benzene / 2 h / Heating 3: 30percent H2O2, conc. HCl / acetonitrile / 3 h / 50 °C / the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C

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Rx-ID: 21448912 View in Reaxys 311/449 Yield

Conditions & References Reaction Steps: 2 1: 92 percent / PdCl2(PhCN)2 / benzene / 2 h / Heating 2: 30percent H2O2, conc. HCl / acetonitrile / 3 h / 50 °C / the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C With hydrogenchloride, dihydrogen peroxide, bis(benzonitrile)palladium(II) dichloride in acetonitrile, benzene Rao, Darvasula V.; Stuber, Fred A.; Tetrahedron Letters; vol. 22; nb. 25; (1981); p. 2337 - 2340 View in Reaxys

Rx-ID: 21449231 View in Reaxys 312/449 Yield

Conditions & References Reaction Steps: 2 1: 100 percent / PdCl2(PhCN)2 / benzene / 2 h / Heating 2: 30percent H2O2, conc. HCl / acetonitrile / 3 h / 50 °C / the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C With hydrogenchloride, dihydrogen peroxide, bis(benzonitrile)palladium(II) dichloride in acetonitrile, benzene Rao, Darvasula V.; Stuber, Fred A.; Tetrahedron Letters; vol. 22; nb. 25; (1981); p. 2337 - 2340 View in Reaxys O

Rx-ID: 21469405 View in Reaxys 313/449 Yield

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With hydrogenchloride, phosphoric acid, dihydrogen peroxide, bis(benzonitrile)palladium(II) dichloride in acetonitrile, benzene Rao, Darvasula V.; Stuber, Fred A.; Tetrahedron Letters; vol. 22; nb. 25; (1981); p. 2337 - 2340 View in Reaxys Reaction Steps: 3 1: 80 percent / 85percent phosphoric acid / 4 h / Ambient temperature 2: 92 percent / PdCl2(PhCN)2 / benzene / 2 h / Heating 3: 30percent H2O2, conc. HCl / acetonitrile / 3 h / 50 °C / the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C With hydrogenchloride, phosphoric acid, dihydrogen peroxide, bis(benzonitrile)palladium(II) dichloride in acetonitrile, benzene Rao, Darvasula V.; Stuber, Fred A.; Tetrahedron Letters; vol. 22; nb. 25; (1981); p. 2337 - 2340 View in Reaxys Reaction Steps: 3 1: 80 percent / 85percent phosphoric acid / 4 h / Ambient temperature 2: 90.6 percent / PdCl2(PhCN)2 / benzene / 2 h / Heating 3: 30percent H2O2, conc. HCl / acetonitrile / 3 h / 50 °C / the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C With hydrogenchloride, phosphoric acid, dihydrogen peroxide, bis(benzonitrile)palladium(II) dichloride in acetonitrile, benzene Rao, Darvasula V.; Stuber, Fred A.; Tetrahedron Letters; vol. 22; nb. 25; (1981); p. 2337 - 2340 View in Reaxys

OH OH

Rx-ID: 21477840 View in Reaxys 314/449 Yield

Conditions & References Reaction Steps: 2 1: pyridine / 2.5 h / 3 °C 2: acetic acid / rate constant: 171.4E5 With pyridine in acetic acid Wistuba, Eckehardt; Ruechardt, Christoph; Tetrahedron Letters; vol. 22; nb. 41; (1981); p. 4069 - 4072 View in Reaxys O+ N

(v4)

N N N(v4)Co (v4) N N (v6) (v4) N

F (v4)

F B

(v5)

(v6) –N (v3) + (v4) (v4) N – Co (v3)

F N

(v4)

Rx-ID: 27050641 View in Reaxys 315/449 Yield 26 %

Conditions & References With 1-hydroxycyclopentane in 1,2-dichloro-ethane, byproducts: BF3-pyridine complex, H2O; under Ar addn. of BF3*Et2O to mixt. of alcohol and complex in (CH2)2Cl2, further addn. of BF3*Et2O, heating in 60°C oil bath for 60 min,addn. 1 drop of pyridine in hexane, removing BF3-pyridine complex pptd.; solvent removing in vac., addn. of petroleum ether to resulting oil, filtration, drying under Ar Tovrog,Benjamin S.; Diamond, Steven E.; Mares, Frank; Szalkiewicz, Andrew; Journal of the American Chemical Society; vol. 103; nb. 12; (1981); p. 3522 - 3526 ; (from Gmelin) View in Reaxys

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Rx-ID: 1507151 View in Reaxys 316/449 Yield

Conditions & References Product distribution Bauduin, G.; Bondon, D.; Pietrasanta, Y.; Pucci, B.; Tetrahedron; vol. 36; nb. 2; (1980); p. 245 - 254 View in Reaxys O

Rx-ID: 1515129 View in Reaxys 317/449 Yield

Conditions & References Product distribution Bauduin, G.; Bondon, D.; Pietrasanta, Y.; Pucci, B.; Tetrahedron; vol. 36; nb. 2; (1980); p. 245 - 254 View in Reaxys N N

Rx-ID: 1581947 View in Reaxys 318/449 Yield 2.5 %, 1 %, 3.3 %, 59.3 %

Conditions & References in benzene, Irradiation, addition of methanol in the dark after irradiation, nondegassed solvent, Product distribution, Mechanism Tomioka, Hideo; Okuno, Hiroshi; Izawa, Yasuji; Journal of Organic Chemistry; vol. 45; nb. 26; (1980); p. 5278 5283 View in Reaxys OH

Rx-ID: 1976886 View in Reaxys 319/449 Yield 14 % Chromat., 41 % Chromat., 36 % Chromat., 9 % Chromat. 9 % Chromat., 41 % Chromat., 36 % Chromat., 14 % Chromat.

Conditions & References With oxygen, T= 60 °C , p= 759.8Torr Blau, K.; Mueller, U.; Pritzkow, W.; Schmidt-Renner, W.; Sedshaw, Z.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 6; (1980); p. 915 - 932 View in Reaxys

With oxygen, T= 60 °C , p= 759.8Torr , Title compound not separated from byproducts Blau, K.; Mueller, U.; Pritzkow, W.; Schmidt-Renner, W.; Sedshaw, Z.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 6; (1980); p. 915 - 932 View in Reaxys

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9 % Chromat., 14 % Chromat., 41 % Chromat., 36 % Chromat.

With oxygen, T= 60 °C , p= 759.8Torr , Mechanism Blau, K.; Mueller, U.; Pritzkow, W.; Schmidt-Renner, W.; Sedshaw, Z.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 6; (1980); p. 915 - 932 View in Reaxys

O HO

Rx-ID: 2340736 View in Reaxys 320/449 Yield

Conditions & References With aluminum isopropoxide in benzene, T= 80 °C , -ΔGox, Equilibrium constant, Thermodynamic data Paul, Mueller; Blanc, Jacky; Helvetica Chimica Acta; vol. 63; nb. 7; (1980); p. 1759 - 1766 View in Reaxys

N Cl

NH 2

Rx-ID: 3063996 View in Reaxys 321/449 Yield

Conditions & References

43 %, 3 %, in methanol, Time= 12h, Irradiation, photolysis in presence of sensitizer, photolysis in methanol-d4 for 6 h, Product 18 %, 5 % distribution, Mechanism Feld, W. A.; Serve, M. P.; Journal of Heterocyclic Chemistry; vol. 17; (1980); p. 825 - 827 View in Reaxys

N Cl

H N

O Cl

NH 2

Rx-ID: 3063997 View in Reaxys 322/449 Yield

Conditions & References

43 %, 3 %, in cyclohexane, Time= 12h, Irradiation, Product distribution, Mechanism 11 %, 5 %, Feld, W. A.; Serve, M. P.; Journal of Heterocyclic Chemistry; vol. 17; (1980); p. 825 - 827 9 %, 5 % View in Reaxys

O N

Cl N

NH 2

Rx-ID: 3063999 View in Reaxys 323/449 Yield

Conditions & References

47 %, 3 %, in acetonitrile, Time= 12h, Irradiation, photolysis in presence of sensitizer, Product distribution, Mechanism 21 % Feld, W. A.; Serve, M. P.; Journal of Heterocyclic Chemistry; vol. 17; (1980); p. 825 - 827 View in Reaxys

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O O O

Rx-ID: 3112338 View in Reaxys 324/449 Yield

Conditions & References in decane, T= 0 °C , Irradiation, Title compound not separated from byproducts Kopecky, Karl R.; Sastre, Juan A. Lopez; Canadian Journal of Chemistry; vol. 58; nb. 19; (1980); p. 2089 - 2092 View in Reaxys With 1,5-diphenyl-1,4-pentadiene-3-one in benzene, T= 40.9 °C , Irradiation, Ea, ΔS(excit.), Kinetics, Thermodynamic data, Product distribution Kopecky, Karl R.; Sastre, Juan A. Lopez; Canadian Journal of Chemistry; vol. 58; nb. 19; (1980); p. 2089 - 2092 View in Reaxys

O HO

Rx-ID: 3125077 View in Reaxys 325/449 Yield

Conditions & References T= 320 °C , presence of solvent, Rate constant, Mechanism Fedyanin, N. P.; J. Appl. Chem. USSR (Engl. Transl.); vol. 53; nb. 10; (1980); p. 2306 - 2309,1755 - 1758 View in Reaxys –O

O Na + N

Rx-ID: 3172200 View in Reaxys 326/449 Yield

Conditions & References

100 %

With hydrogenchloride, Time= 0.0416667h, Ambient temperature, pH = 4-6, regeneration of aldehyde, Product distribution Ohta, Shunsaku; Okamoto, Masao; Chemical & Pharmaceutical Bulletin; vol. 28; nb. 6; (1980); p. 1917 - 1919 View in Reaxys

Rx-ID: 3345337 View in Reaxys 327/449 Yield 52 %, 42 %

Conditions & References With sodium dithionite, sodium hydrogencarbonate in water, Time= 4h, Heating de Vries, Johannes G.; Kellogg, Richard M.; Journal of Organic Chemistry; vol. 45; nb. 21; (1980); p. 4126 - 4129 View in Reaxys

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O O O

Rx-ID: 3476364 View in Reaxys 328/449 Yield

Conditions & References With dimethylsulfide in methanol, dry ice-acetone to room temperature, Yields of byproduct given Wrobel, Jay; Cook, J. M.; Synthetic Communications; vol. 10; nb. 4; (1980); p. 333 - 338 View in Reaxys With dimethylsulfide in methanol, dry ice-acetone to room temperature, Yield given Wrobel, Jay; Cook, J. M.; Synthetic Communications; vol. 10; nb. 4; (1980); p. 333 - 338 View in Reaxys O

η5-cyclopentadienyl-(triphenylphosphino)-cobaltacyclopentane

Rx-ID: 5929731 View in Reaxys 329/449 Yield

Conditions & References

33 %

in benzene, Time= 168h, p= 33097.9Torr , Ambient temperature Wakatsuki, Yasuo; Nomura, Okio; Tone, Hiroatsu; Yamazaki, Hiroshi; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 1344 - 1349 View in Reaxys O

Rx-ID: 1072455 View in Reaxys 330/449 Yield

Conditions & References T= 20 °C , Equilibrium constant Bigler,P.; Neuenschwander,M.; Helvetica Chimica Acta; vol. 61; (1978); p. 2165 - 2175 View in Reaxys

Sn O

O O

Rx-ID: 26756965 View in Reaxys 331/449 Yield 28 %, 72 %

Conditions & References byproducts: (C4H9)3SnCH(CH3)COOCH3, CO2; 60 percent decompn. at 180°C/5 Torr within 8 h Didier, P.; Pommier, J. C.; Journal of Organometallic Chemistry; vol. 150; (1978); p. 203 - 214 ; (from Gmelin) View in Reaxys

28 %, 72 %

byproducts: (C4H9)3SnCH(CH3)COOCH3, CO2; 60 percent decompn. at 180°C/5 Torr within 8 h vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.1.7, page 69 - 97 ; (from Gmelin) View in Reaxys

32 %, 68 %

byproducts: (C4H9)3SnCH(CH3)COOCH3, CO2; 63 percent decompn. at 200°C/5 Torr within 5 h Didier, P.; Pommier, J. C.; Journal of Organometallic Chemistry; vol. 150; (1978); p. 203 - 214 ; (from Gmelin) View in Reaxys

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32 %, 68 %

byproducts: (C4H9)3SnCH(CH3)COOCH3, CO2; 63 percent decompn. at 200°C/5 Torr within 5 h vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.1.7, page 69 - 97 ; (from Gmelin) View in Reaxys

O Sn

Rx-ID: 26755221 View in Reaxys 332/449 Yield

Conditions & References With NO{BF4} in dichloromethane Olah, G. A.; Ho, T. L.; Synthesis; (1976); p. 609 - 610 ; (from Gmelin) View in Reaxys With NO{BF4} in dichloromethane vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.1.6, page 64 - 69 ; (from Gmelin) View in Reaxys O

O Cl O Cl

Rx-ID: 952575 View in Reaxys 333/449 Yield

Conditions & References With perchloric acid Jaeger,G.; Chemische Berichte; vol. 105; (1972); p. 137 - 149 View in Reaxys

Br O H H H H

H H H H

racemate

Rx-ID: 26755726 View in Reaxys 334/449 Yield 88 %

Conditions & References decompn. at 150°C for 0.5 h Delmond; Pommier; Tetrahedron Letters; (1968); p. 6147 ; (from Gmelin) View in Reaxys

88 %

decompn. at 150°C for 0.5 h Delmond, Bernard; Pommier, Jean-Claude; Valade, Jacques; Journal of Organometallic Chemistry; vol. 35; nb. 1; (1972); p. 91 - 104 View in Reaxys vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.1.7, page 69 - 97 ; (from Gmelin) View in Reaxys

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Cl Sn

H H

racemate

Rx-ID: 26755743 View in Reaxys 335/449 Yield

Conditions & References

79 %

decompn. at 210°C for 0.5 h Delmond, Bernard; Pommier, Jean-Claude; Valade, Jacques; Journal of Organometallic Chemistry; vol. 35; nb. 1; (1972); p. 91 - 104 View in Reaxys vol. Sn: Org.Comp.12; 1.4.1.1.1.5.2.1.7, page 69 - 97 ; (from Gmelin) View in Reaxys

O Cl

Cl OH

Rx-ID: 1130981 View in Reaxys 336/449 Yield

Conditions & References (i) Pb(OAc)4, aq. AcOH, (ii) Pd-C, H2, HClO4, aq. EtOH, Multistep reaction Burgstahler,A.W. et al.; Journal of Organic Chemistry; vol. 31; (1966); p. 3516 - 3522 View in Reaxys

carbon monoxide O

octacarbonyl dicobalt

Rx-ID: 5957084 View in Reaxys 337/449 Yield

Conditions & References T= 110 °C , p= 152000Torr Patent; Lonza A.G.; US2851486; (1956) View in Reaxys Natta; Albanesi; Chimica e l'Industria (Milan, Italy); vol. 48; (1966); p. 1157 View in Reaxys

HO HO

O Cl

cyclopentanone-vapour

Cl Cl

Rx-ID: 22532150 View in Reaxys 338/449 Yield

Conditions & References Reaction Steps: 2 1: H2 / Pd-C / aq. ethanol 2: (i) Pb(OAc)4, aq. AcOH, (ii) Pd-C, H2, HClO4, aq. EtOH With hydrogen, palladium on activated charcoal in ethanol Burgstahler,A.W. et al.; Journal of Organic Chemistry; vol. 31; (1966); p. 3516 - 3522 View in Reaxys

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H 2N N

S NH

H N

O NH 2

NH 2

Rx-ID: 1094069 View in Reaxys 339/449 Yield

Conditions & References With water, T= 25 - 50 °C , Kinetics, Equilibrium constant Fiarman,I.D.; Gettler,J.D.; Journal of the American Chemical Society; vol. 84; (1962); p. 961 - 966 View in Reaxys

NH 2

H N

H 2N

NH 2

Rx-ID: 1111603 View in Reaxys 340/449 Yield

Conditions & References With water, T= 25 - 50 °C , Kinetics, Equilibrium constant Brooks,D.W.; Gettler,J.D.; Journal of Organic Chemistry; vol. 27; (1962); p. 4469 - 4475 View in Reaxys

molybdenum (IV)-sulfide Rx-ID: 7062573 View in Reaxys 341/449 Yield

Conditions & References T= 300 °C Landa et al.; Collection of Czechoslovak Chemical Communications; vol. 24; (1959); p. 1036,1038,1039 View in Reaxys N OH

HO N

Rx-ID: 191032 View in Reaxys 342/449 Yield

Conditions & References T= 25 °C , Equilibrium constant Wheeler; Zabicky; Canadian Journal of Chemistry; vol. 36; (1958); p. 656 View in Reaxys El-Abbady; Journal of Organic Chemistry; vol. 21; (1956); p. 828 View in Reaxys Equilibrium constant Prelog; Kobelt; Helvetica Chimica Acta; vol. 32; (1949); p. 1187,1191 View in Reaxys Ruzicka; Plattner; Wild; Helvetica Chimica Acta; vol. 28; (1945); p. 613,615 View in Reaxys

O O

H 2N

O H

N OH

Rx-ID: 5687610 View in Reaxys 343/449

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Yield

Conditions & References Bartlett et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 126,135 View in Reaxys

Rx-ID: 5687613 View in Reaxys 344/449 Yield

Conditions & References T= 30 °C , Equilibrium constant Newman; Harper; Journal of the American Chemical Society; vol. 80; (1958); p. 6350,6353 View in Reaxys N

aqueous dioxane

Rx-ID: 7918742 View in Reaxys 345/449 Yield

Conditions & References T= 25 °C , Equilibrium constant Wheeler; Mateos; Canadian Journal of Chemistry; vol. 36; (1958); p. 712,713 View in Reaxys

aq.-ethanolic NaOH-solution

Rx-ID: 5687611 View in Reaxys 346/449 Yield

Conditions & References House; Wasson; Journal of the American Chemical Society; vol. 79; (1957); p. 1488,1490 View in Reaxys O

Rx-ID: 5929732 View in Reaxys 347/449 Yield

Conditions & References T= 0 °C , Rate constant Hawthorne; Journal of the American Chemical Society; vol. 79; (1957); p. 2510,2512 View in Reaxys O OH

(v1)

-1

Ag+ O

Cl OO

Rx-ID: 7446072 View in Reaxys 348/449 Yield

Conditions & References T= 50 °C , Rate constant Hawthorne; Strahm; Journal of the American Chemical Society; vol. 79; (1957); p. 2515,2517 View in Reaxys

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aq.-ethanolic silver nitrate solution Rx-ID: 7446073 View in Reaxys 349/449 Yield

Conditions & References Braude; Forbes; Journal of the Chemical Society; (1951); p. 1755,1760 View in Reaxys Goering et al.; Journal of the American Chemical Society; vol. 79; (1957); p. 2502,2503 View in Reaxys O

acidocyclopentane Rx-ID: 5687608 View in Reaxys 350/449 Yield

Conditions & References With chloroform, sulfuric acid Boyer et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 325 View in Reaxys N

OH HO

S OO

Rx-ID: 7446080 View in Reaxys 351/449 Yield

Conditions & References Boyer et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 325 View in Reaxys HO

O O

Rx-ID: 256725 View in Reaxys 352/449 Yield

Conditions & References With hydrogen bromide Crombie; Hancock; Linstead; Journal of the Chemical Society; (1953); p. 3502 View in Reaxys O O

O O

Rx-ID: 258935 View in Reaxys 353/449 Yield

Conditions & References With hydrogen bromide Crombie; Hancock; Linstead; Journal of the Chemical Society; (1953); p. 3502 View in Reaxys Reaction Steps: 2 1: aqueous KOH-solution 2: HBr With potassium hydroxide, hydrogen bromide Crombie; Hancock; Linstead; Journal of the Chemical Society; (1953); p. 3502

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View in Reaxys

Rx-ID: 315591 View in Reaxys 354/449 Yield

Conditions & References With dichloromethane, ozone, T= -80 °C Criegee et al.; Justus Liebigs Annalen der Chemie; vol. 583; (1953); p. 1,28 View in Reaxys O O

O HO

OH O

O O

Rx-ID: 7061520 View in Reaxys 355/449 Yield

Conditions & References Crombie; Hancock; Linstead; Journal of the Chemical Society; (1953); p. 3502 View in Reaxys HO

OH O

Rx-ID: 7061521 View in Reaxys 356/449 Yield

Conditions & References Crombie; Hancock; Linstead; Journal of the Chemical Society; (1953); p. 3502 View in Reaxys

O O

OH O

Rx-ID: 7061522 View in Reaxys 357/449 Yield

Conditions & References Crombie; Hancock; Linstead; Journal of the Chemical Society; (1953); p. 3502 View in Reaxys

OH O

Rx-ID: 7061523 View in Reaxys 358/449 Yield

Conditions & References Crombie; Hancock; Linstead; Journal of the Chemical Society; (1953); p. 3502 View in Reaxys

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O O

OH O

O O

Rx-ID: 7061524 View in Reaxys 359/449 Yield

Conditions & References Crombie; Hancock; Linstead; Journal of the Chemical Society; (1953); p. 3502 View in Reaxys

(v4)

Rx-ID: 7446081 View in Reaxys 360/449 Yield

Conditions & References T= -80 °C Criegee et al.; Justus Liebigs Annalen der Chemie; vol. 583; (1953); p. 1,28 View in Reaxys O

O N

Rx-ID: 7061513 View in Reaxys 361/449 Yield

Conditions & References T= 300 °C , p= 330978Torr Bridson-Jones et al.; Journal of the Chemical Society; (1951); p. 2999,3006 View in Reaxys

O H

H 2N

Rx-ID: 7061528 View in Reaxys 362/449 Yield

Conditions & References T= 0 °C , und 18grad, Equilibrium constant Poggi; Serchi; Gazzetta Chimica Italiana; vol. 80; (1950); p. 385 View in Reaxys

OH NH 2

O N

racemate

Rx-ID: 8258082 View in Reaxys 363/449 Yield

Conditions & References Mousseron; Jacquier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 229; (1949); p. 216; Bulletin de la Societe Chimique de France; (1950); p. 238,243 View in Reaxys

O OH

O HO

S OO

1,2c-dihydroxy-cyclopentane-1r,carboxylic acid (?)

Rx-ID: 5687607 View in Reaxys 364/449

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2017-10-23 09:43:02

Yield

Conditions & References Mousseron; Jullien; Winternitz; Bulletin de la Societe Chimique de France; (1948); p. 878,885 View in Reaxys

nitrogen

cobalt catalyst O

butane, Rx-ID: 5727121 View in Reaxys 365/449 Yield

Conditions & References T= 200 - 300 °C Wilson; Journal of the American Chemical Society; vol. 70; (1948); p. 1313 View in Reaxys O

nitrogen

nickel

butane, Rx-ID: 5727122 View in Reaxys 366/449

Yield

Conditions & References T= 200 - 300 °C Wilson; Journal of the American Chemical Society; vol. 70; (1948); p. 1313 View in Reaxys O

2.3-dihydro-pyran Rx-ID: 5929729 View in Reaxys 367/449 Yield

Conditions & References With nickel-copper catalyst, hydrogen Wilson; Journal of the American Chemical Society; vol. 70; (1948); p. 1313 View in Reaxys With hydrogen, nickel Wilson; Journal of the American Chemical Society; vol. 70; (1948); p. 1313 View in Reaxys With cobalt-copper catalyst, hydrogen Wilson; Journal of the American Chemical Society; vol. 70; (1948); p. 1313 View in Reaxys With cobalt catalyst, nitrogen, T= 250 - 300 °C Wilson; Journal of the American Chemical Society; vol. 70; (1948); p. 1313 View in Reaxys O

O HO

OH O

K F Rx-ID: 6682680 View in Reaxys 368/449

Yield

Conditions & References T= 250 - 280 °C

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Nesmejanow; Petscherskaja; Urezkaja; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1948); p. 240,243; ; (1948); p. 4924 View in Reaxys O

B O

Rx-ID: 7061529 View in Reaxys 369/449 Yield

Conditions & References Hauser; Swamer; Ringler; Journal of the American Chemical Society; vol. 70; (1948); p. 4023,4025 View in Reaxys OH

air oxygen Rx-ID: 7061525 View in Reaxys 370/449 Yield

Conditions & References T= 140 °C , p= 20594.2Torr Patent; Phillips Petr. Co.; US2452741; (1947) View in Reaxys

copper

Rx-ID: 7076710 View in Reaxys 371/449 Yield

Conditions & References T= 150 - 275 °C , Equilibrium constant Cubberley; Mueller; Journal of the American Chemical Society; vol. 68; (1946); p. 1150 View in Reaxys

O NH 2

zinc oxide

racemate

Rx-ID: 8258081 View in Reaxys 372/449 Yield

Conditions & References T= 50 °C , Geschwindigkeit.Hydrolysis Mousseron et al.; Bulletin de la Societe Chimique de France; (1946); p. 629,632 View in Reaxys O

cyclopentanol-vapour Rx-ID: 5929736 View in Reaxys 373/449 Yield

Conditions & References With iron, zinc, T= 425 °C Patent; I.G. Farbenind.; DE743004; (1940) View in Reaxys With zinc/copper couple, T= 450 °C Patent; Phillips Petr. Co.; US2377412; (1944) View in Reaxys Patent; I.G. Farbenind.; DE765200; (1939);

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View in Reaxys OH

copper-zinc-alloyene Rx-ID: 7061514 View in Reaxys 374/449 Yield

Conditions & References T= 450 °C , Ueberleiten des Dampfes Patent; I.G. Farbenind.; DE765200; (1939); View in Reaxys T= 290 - 340 °C , Ueberleiten des Dampfes Patent; Phillips Petr. Co.; US2377412; (1944) View in Reaxys O Br

oxygen

Rx-ID: 7061517 View in Reaxys 375/449 Yield

Conditions & References T= 185 °C Patent; Shell Devel. Co.; US2391740; (1944) View in Reaxys

HO HO

O O

Rx-ID: 120750 View in Reaxys 376/449 Yield

Conditions & References With potassium permanganate, sulfuric acid Buchman; Sargent; Journal of Organic Chemistry; vol. 7; (1942); p. 140,145 View in Reaxys With sulfuric acid, lead dioxide Wallach; Justus Liebigs Annalen der Chemie; vol. 414; (1918); p. 311; Justus Liebigs Annalen der Chemie; vol. 437; (1924); p. 174 View in Reaxys

Rx-ID: 596247 View in Reaxys 377/449 Yield

Conditions & References With aluminium oxide catalyst, chromium, T= 160 - 250 °C , p= 3677.5Torr Patent; Phillips Petr. Co.; US2371794; (1942) View in Reaxys With copper-nickel catalyst, T= 160 - 250 °C , p= 3677.5Torr Patent; Phillips Petr. Co.; US2371794; (1942) View in Reaxys

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sodium

I O

Rx-ID: 5687612 View in Reaxys 378/449 Yield

Conditions & References Erhitzen des Reaktionsprodukts mit wss.-aethanol. Natronlauge Hudson; Robinson; Journal of the Chemical Society; (1942); p. 691 View in Reaxys

aqueous KOH

O HO

steam

O OH

Rx-ID: 7918743 View in Reaxys 379/449 Yield

Conditions & References und Ansaeuern des Reaktionsgemisches mit wss.H2SO4 Mannich; Chemische Berichte; vol. 74; (1941); p. 565,568 View in Reaxys

O OH

palladium/charcoal

rel-configuration

Rx-ID: 8258079 View in Reaxys 380/449 Yield

Conditions & References Hydrogenation Clutterbuck et al.; Biochemical Journal; vol. 34; (1940); p. 664,666, 672 View in Reaxys O

O HO

OH O

Rx-ID: 102822 View in Reaxys 381/449 Yield

Conditions & References Bei der thermischen Zersetzung des Bariumsalzes Neunhoeffer; Paschke; Chemische Berichte; vol. 72; (1939); p. 919,927 View in Reaxys

Rx-ID: 316613 View in Reaxys 382/449 Yield

Conditions & References T= 190 °C Neunhoeffer; Paschke; Chemische Berichte; vol. 72; (1939); p. 919,927 View in Reaxys

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adipic acid vapour

Rx-ID: 5929743 View in Reaxys 383/449 Yield

Conditions & References With ammonia, thorium(IV) dioxide, T= 350 °C Patent; I.G. Farbenind.; DE743967; (1939); View in Reaxys With aluminum oxide, ammonia, T= 350 °C Patent; I.G. Farbenind.; DE743967; (1939); View in Reaxys O

Rx-ID: 302593 View in Reaxys 384/449 Yield

Conditions & References With sulfuric acid, T= 130 - 135 °C Wenus-Danilowa; Zhurnal Obshchei Khimii; vol. 8; (1938); p. 1179,1188; Chem. Zentralbl.; vol. 111; nb. I; (1940); p. 1490 View in Reaxys With ethanol, mercury dichloride, T= 100 °C Wenus-Danilowa; Zhurnal Obshchei Khimii; vol. 8; (1938); p. 1179,1188; Chem. Zentralbl.; vol. 111; nb. I; (1940); p. 1490 View in Reaxys

O OH

Rx-ID: 444965 View in Reaxys 385/449 Yield

Conditions & References T= 165 - 220 °C Cornubert et al.; Bulletin de la Societe Chimique de France; vol. <5> 5; (1938); p. 1490,1500; Bulletin de la Societe Chimique de France; vol. <5> 6; (1939); p. 132,132 Anm. 3 View in Reaxys O

OH HO

S OO

Rx-ID: 7446071 View in Reaxys 386/449 Yield

Conditions & References T= 135 °C Wenus-Danilowa; Zhurnal Obshchei Khimii; vol. 8; (1938); p. 1179,1188; Chem. Zentralbl.; vol. 111; nb. I; (1940); p. 1490 View in Reaxys

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O OH

HgCl2 O

Rx-ID: 7446075 View in Reaxys 387/449 Yield

Conditions & References T= 100 °C Wenus-Danilowa; Zhurnal Obshchei Khimii; vol. 8; (1938); p. 1179,1188; Chem. Zentralbl.; vol. 111; nb. I; (1940); p. 1490 View in Reaxys

O OO O O

O O

Rx-ID: 523152 View in Reaxys 388/449 Yield

Conditions & References With sulfuric acid Guha; Seshadriengar; Chemische Berichte; vol. 69; (1936); p. 1212,1216 View in Reaxys NH 2

copper

oxygen Rx-ID: 5929737 View in Reaxys 389/449

Yield

Conditions & References Demjanow; Schuikina; Zhurnal Obshchei Khimii; vol. 6; (1936); p. 350; Chem. Zentralbl.; vol. 107; nb. II; (1936); p. 1905 View in Reaxys NH 2

osmium(VIII)-oxide

oxygen Rx-ID: 5929738 View in Reaxys 390/449

Yield

Conditions & References Demjanow; Schuikina; Zhurnal Obshchei Khimii; vol. 6; (1936); p. 350; Chem. Zentralbl.; vol. 107; nb. II; (1936); p. 1905 View in Reaxys O

sodium Rx-ID: 7061530 View in Reaxys 391/449

Yield

Conditions & References T= -10 °C Kuhn; Koehler; Koehler; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 242; (1936); p. 186 View in Reaxys

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O OO O O

OH HO

O O

S OO

Rx-ID: 8258077 View in Reaxys 392/449 Yield

Conditions & References Guha; Seshadriengar; Chemische Berichte; vol. 69; (1936); p. 1212,1216 View in Reaxys O

Rx-ID: 102823 View in Reaxys 393/449 Yield

Conditions & References T= 313 - 320 °C Vogel; Journal of the Chemical Society; (1929); p. 732 View in Reaxys T= 315 - 320 °C Vogel; Journal of the Chemical Society; (1929); p. 732 View in Reaxys CO2-Strom Aschan; Chemische Berichte; vol. 45; (1912); p. 1605; Justus Liebigs Annalen der Chemie; vol. 383; (1911); p. 58 View in Reaxys

natrium carbonatalkaline permanganate

Rx-ID: 7446077 View in Reaxys 394/449 Yield

Conditions & References Kandiah; Linstead; Journal of the Chemical Society; (1929); p. 2148 View in Reaxys OH

O HO

Rx-ID: 211639 View in Reaxys 395/449 Yield

Conditions & References bei der Ozonspaltung Jupp; Kon; Lockton; Journal of the Chemical Society; (1928); p. 1642 View in Reaxys

'cis'-1.2.3.4.10.11-hexahydro-carbazole

Rx-ID: 5687605 View in Reaxys 396/449 Yield

Conditions & References 9-<1-cyano-cyclopentyl>-'cis'-1.2.3.4.10.11-hexahydro-carbazole

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Plant; Rippon; Journal of the Chemical Society; (1928); p. 1907 Anm. View in Reaxys

'cis'-1.2.3.4.10.11-hexahydro-carbazole

Rx-ID: 5687606 View in Reaxys 397/449 Yield

Conditions & References 9-<1-cyano-cyclopentyl>-'cis'-1.2.3.4.10.11-hexahydro-carbazole Plant; Rippon; Journal of the Chemical Society; (1928); p. 1907 Anm. View in Reaxys

tetrahydropentindole

Rx-ID: 5746575 View in Reaxys 398/449 Yield

Conditions & References Plant; Rippon; Journal of the Chemical Society; (1928); p. 1907 Anm. View in Reaxys

Rx-ID: 454741 View in Reaxys 399/449 Yield

Conditions & References bei der Ozonspaltung Kon; Narayanan; Journal of the Chemical Society; (1927); p. 1544 View in Reaxys

O O

Rx-ID: 458744 View in Reaxys 400/449 Yield

Conditions & References bei der Ozonspaltung Kon; Narayanan; Journal of the Chemical Society; (1927); p. 1544 View in Reaxys

O HO

OH O

Rx-ID: 164436 View in Reaxys 401/449 Yield

Conditions & References bei der Ozonspaltung

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Kon; Nutland; Journal of the Chemical Society; (1926); p. 3108 View in Reaxys

Cl O

O O

Rx-ID: 211552 View in Reaxys 402/449 Yield

Conditions & References bei der Ozonisierung und nachfolgenden Zersetzung mit verd. Schwefelsaeure Kon; Speight; Journal of the Chemical Society; (1926); p. 2733 View in Reaxys OH

OH O

HO O

Rx-ID: 211586 View in Reaxys 403/449 Yield

Conditions & References bei der Ozonisierung und Zersetzung des Reaktionsprodukts mit verd. Schwefelsaeure Kon; Speight; Journal of the Chemical Society; (1926); p. 2733 View in Reaxys O

salt of/the/ adipic acid Rx-ID: 5929740 View in Reaxys 404/449 Yield

Conditions & References Thermolysis Godchot; Bedos; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 394 View in Reaxys Ruzicka et al.; Helvetica Chimica Acta; vol. 9; (1926); p. 515 View in Reaxys O

2-acetoxy-cyclopentanone-(1) Rx-ID: 5929730 View in Reaxys 405/449 Yield

Conditions & References With hydrogen, palladium Staudinger; Ruzicka; Helvetica Chimica Acta; vol. 7; (1924); p. 385 View in Reaxys O

cyclopentanol-(2)-one-(1) Rx-ID: 5929735 View in Reaxys 406/449 Yield

Conditions & References With sodium amalgam, carbon dioxide Staudinger; Ruzicka; Helvetica Chimica Acta; vol. 7; (1924); p. 385

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View in Reaxys O

hydrogen

palladium Rx-ID: 7061518 View in Reaxys 407/449

Yield

Conditions & References Staudinger; Ruzicka; Helvetica Chimica Acta; vol. 7; (1924); p. 385 View in Reaxys O

sodium amalgam

Rx-ID: 7061519 View in Reaxys 408/449 Yield

Conditions & References Staudinger; Ruzicka; Helvetica Chimica Acta; vol. 7; (1924); p. 385 View in Reaxys O O

hydrogen

palladium Rx-ID: 7446078 View in Reaxys 409/449

Yield

Conditions & References Staudinger; Ruzicka; Helvetica Chimica Acta; vol. 7; (1924); p. 385 View in Reaxys

moist chloroform

Rx-ID: 7061516 View in Reaxys 410/449 Yield

Conditions & References bei der Ozonspaltung Birch; Kon; Journal of the Chemical Society; vol. 123; (1923); p. 2447 View in Reaxys O

Br Br

Rx-ID: 276925 View in Reaxys 411/449 Yield

Conditions & References With water, massicot Demjanow; Dojarenko; Chemische Berichte; vol. 55; (1922); p. 2725 View in Reaxys Gustavson; Bulatow; Journal fuer Praktische Chemie (Leipzig); vol. <2> 56; (1897); p. 93 View in Reaxys With water, massicot, T= 135 - 140 °C , Konstitution von Edukt 1: Demjanow, Dojarenko, B. 55, 2727, 2732. Gustavson; Bulatow; Journal fuer Praktische Chemie (Leipzig); vol. <2> 56; (1897); p. 93 View in Reaxys

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Cl HO

Rx-ID: 454004 View in Reaxys 412/449 Yield

Conditions & References Demjanow; Dojarenko; Chemische Berichte; vol. 55; (1922); p. 2725 View in Reaxys

lead oxide

1-methylol-cyclobutanol-(1)

Rx-ID: 7061527 View in Reaxys 413/449 Yield

Conditions & References T= 20 °C Demjanow; Dojarenko; Chemische Berichte; vol. 55; (1922); p. 2725 View in Reaxys O

methylenecyclobutane dibromide O

Rx-ID: 7446082 View in Reaxys 414/449 Yield

Conditions & References With water, massicot Demjanow; Dojarenko; Chemische Berichte; vol. 55; (1922); p. 2725 View in Reaxys O

lead (II)-oxide

Rx-ID: 8258083 View in Reaxys 415/449 Yield

Conditions & References Demjanow; Dojarenko; Chemische Berichte; vol. 55; (1922); p. 2725 View in Reaxys O

O HO

Rx-ID: 6682683 View in Reaxys 416/449 Yield

Conditions & References mit Katalysatoren Chavanne; Simon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 168; (1919); p. 1326 View in Reaxys Sabatier; Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 987 View in Reaxys Patent; Bayer and Co.; DE256622; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 48 View in Reaxys

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HO HO

O OH

O HO

lead dioxide

S OO

Rx-ID: 6682681 View in Reaxys 417/449 Yield

Conditions & References Wallach; Justus Liebigs Annalen der Chemie; vol. 414; (1918); p. 311; Justus Liebigs Annalen der Chemie; vol. 437; (1924); p. 174 View in Reaxys O

Rx-ID: 22042037 View in Reaxys 418/449 Yield

Conditions & References Reaction Steps: 2 1: diluted KOH-solution 2: PbO2; diluted sulfuric acid With potassium hydroxide, sulfuric acid, lead dioxide Wallach; Justus Liebigs Annalen der Chemie; vol. 414; (1918); p. 311; Justus Liebigs Annalen der Chemie; vol. 437; (1924); p. 174 View in Reaxys O

Rx-ID: 22059906 View in Reaxys 419/449 Yield

Conditions & References Reaction Steps: 3 1: glacial acetic acid; bromine 2: diluted KOH-solution 3: PbO2; diluted sulfuric acid With potassium hydroxide, sulfuric acid, bromine, lead dioxide, acetic acid Wallach; Justus Liebigs Annalen der Chemie; vol. 414; (1918); p. 311; Justus Liebigs Annalen der Chemie; vol. 437; (1924); p. 174 View in Reaxys

potassium permanganate

OH O

HO O

natrium carbonate

Rx-ID: 8258084 View in Reaxys 420/449 Yield

Conditions & References Stobbe; Journal fuer Praktische Chemie (Leipzig); vol. <2> 89; (1914); p. 349 View in Reaxys Stobbe; Fischer; Chemische Berichte; vol. 32; (1899); p. 3355 View in Reaxys

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O O

Rx-ID: 854578 View in Reaxys 421/449 Yield

Conditions & References With water, T= 200 °C , im Rohr Meerwein; Justus Liebigs Annalen der Chemie; vol. 398; (1913); p. 249 View in Reaxys

O H

Rx-ID: 6682679 View in Reaxys 422/449 Yield

Conditions & References T= 200 °C , im geschlossenen Rohr Meerwein; Justus Liebigs Annalen der Chemie; vol. 398; (1913); p. 249 View in Reaxys O O

O E

alcoholic KOH-solution

O O

Rx-ID: 5687609 View in Reaxys 423/449 Yield

Conditions & References Stobbe; Striegler; Journal fuer Praktische Chemie (Leipzig); vol. <2> 86; (1912); p. 241 View in Reaxys O Br

Rx-ID: 38522 View in Reaxys 424/449 Yield

Conditions & References With diethyl ether, magnesium, Behandeln des Reaktionsprodukts mit CO2 v.Braun; Sobecki; Chemische Berichte; vol. 44; (1911); p. 1923 View in Reaxys

M g

O HO

dodecamethylenedicarboxylic acid (?)

Rx-ID: 6728159 View in Reaxys 425/449 Yield

Conditions & References Behandlung des Realktionsproduktes mit CO2 v.Braun; Sobecki; Chemische Berichte; vol. 44; (1911); p. 1921 View in Reaxys

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O O

Mg+

2 Br– +Mg

Rx-ID: 8258078 View in Reaxys 426/449 Yield

Conditions & References v.Braun; Sobecki; Chemische Berichte; vol. 44; (1911); p. 1923 View in Reaxys O

Rx-ID: 385182 View in Reaxys 427/449 Yield

Conditions & References With sulfuric acid Mitchell; Thorpe; Journal of the Chemical Society; vol. 97; (1910); p. 1002 View in Reaxys

O OH HO

CrO3

S OO

Rx-ID: 7061515 View in Reaxys 428/449 Yield

Conditions & References Demjanow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 42; (1910); p. 840; Chem. Zentralbl.; vol. 81; nb. II; (1910); p. 1749 View in Reaxys

diluted KOH-solution

Rx-ID: 7446074 View in Reaxys 429/449 Yield

Conditions & References Harding; Haworth; Journal of the Chemical Society; vol. 97; (1910); p. 497 View in Reaxys

O O

permanganate

Rx-ID: 7446079 View in Reaxys 430/449 Yield

Conditions & References Harding; Haworth; Journal of the Chemical Society; vol. 97; (1910); p. 497 View in Reaxys

OH HO

S OO

O O

Rx-ID: 7918741 View in Reaxys 431/449 Yield

Conditions & References Mitchell; Thorpe; Journal of the Chemical Society; vol. 97; (1910); p. 1002 View in Reaxys

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NH 2 O O

Rx-ID: 22197074 View in Reaxys 432/449 Yield

Conditions & References Reaction Steps: 2 1: hydrochloric acid 2: diluted sulfuric acid With hydrogenchloride, sulfuric acid Mitchell; Thorpe; Journal of the Chemical Society; vol. 97; (1910); p. 1002 View in Reaxys

O N

Rx-ID: 384296 View in Reaxys 433/449 Yield

Conditions & References With sulfuric acid Best; Thorpe; Journal of the Chemical Society; vol. 95; (1909); p. 705 View in Reaxys Reaction Steps: 2 1: sulfuric acid 2: diluted sulfuric acid With sulfuric acid Best; Thorpe; Journal of the Chemical Society; vol. 95; (1909); p. 705 View in Reaxys O

O N

Rx-ID: 827319 View in Reaxys 434/449 Yield

Conditions & References With sulfuric acid Best; Thorpe; Journal of the Chemical Society; vol. 95; (1909); p. 705 View in Reaxys O

O OH HO

S OO

Rx-ID: 5929733 View in Reaxys 435/449 Yield

Conditions & References Best; Thorpe; Journal of the Chemical Society; vol. 95; (1909); p. 705 View in Reaxys

OH HO

S OO

O N

Rx-ID: 7920401 View in Reaxys 436/449

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Yield

Conditions & References Best; Thorpe; Journal of the Chemical Society; vol. 95; (1909); p. 705 View in Reaxys

O O

permanganate

Rx-ID: 8258080 View in Reaxys 437/449 Yield

Conditions & References T= 0 °C Wallach; v. Martius; Chemische Berichte; vol. 42; (1909); p. 147; Justus Liebigs Annalen der Chemie; vol. 365; (1909); p. 274 View in Reaxys O

NH N

Rx-ID: 22191326 View in Reaxys 438/449 Yield

Conditions & References Reaction Steps: 2 1: diluted hydrochloric acid 2: diluted sulfuric acid With hydrogenchloride, sulfuric acid Best; Thorpe; Journal of the Chemical Society; vol. 95; (1909); p. 705 View in Reaxys

O NH 2

Rx-ID: 22197069 View in Reaxys 439/449 Yield

Conditions & References Reaction Steps: 2 1: concentrated hydrochloric acid 2: diluted sulfuric acid With hydrogenchloride, sulfuric acid Best; Thorpe; Journal of the Chemical Society; vol. 95; (1909); p. 705 View in Reaxys Reaction Steps: 3 1: concentrated hydrochloric acid 2: sulfuric acid 3: diluted sulfuric acid With hydrogenchloride, sulfuric acid Best; Thorpe; Journal of the Chemical Society; vol. 95; (1909); p. 705 View in Reaxys O

OH O

Rx-ID: 555389 View in Reaxys 440/449

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Yield

Conditions & References beim langsamen Destillieren das zunaechst entstehende Adipinsaeureanhydrid unter gewoehnlichem Druck Blanc; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 144; (1907); p. 1357; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 779 View in Reaxys

KMnO4-solution Rx-ID: 7446076 View in Reaxys 441/449 Yield

Conditions & References Wallach; Fleischer; Justus Liebigs Annalen der Chemie; vol. 353; (1907); p. 305; Chem. Zentralbl.; vol. 78; nb. II; (1907); p. 53 View in Reaxys HO

potassium permanganate

Rx-ID: 7061526 View in Reaxys 442/449 Yield

Conditions & References T= 0 °C Wallach; Justus Liebigs Annalen der Chemie; vol. 347; (1906); p. 325 View in Reaxys

OH HO

S OO

Rx-ID: 5687604 View in Reaxys 443/449 Yield

Conditions & References Dieckmann; Justus Liebigs Annalen der Chemie; vol. 317; (1901); p. 104 View in Reaxys O

O O

Rx-ID: 22290456 View in Reaxys 444/449 Yield

Conditions & References Reaction Steps: 2 1: Reaktion ueber mehrere Stufen 2: diluted sulfuric acid With sulfuric acid Dieckmann; Justus Liebigs Annalen der Chemie; vol. 317; (1901); p. 104 View in Reaxys O

succinate calcium Rx-ID: 5929741 View in Reaxys 445/449 Yield

Conditions & References bei der Destillation Metzner; Vorlaender; Chemische Berichte; vol. 31; (1898); p. 1886 View in Reaxys

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O HO

furan(?)

OH O

Rx-ID: 7076115 View in Reaxys 446/449 Yield

Conditions & References bei der Destillation des bernteinsauren Calciums Metzner; Vorlaender; Chemische Berichte; vol. 31; (1898); p. 1855 View in Reaxys O–

2+ O Ca

O– H

Rx-ID: 589373 View in Reaxys 447/449 Yield

Conditions & References Bei der Destillation Hentzschel; Wislicenus,J.; Justus Liebigs Annalen der Chemie; vol. 275; (1893); p. 313 View in Reaxys Wallach; Chemische Berichte; vol. 29; (1896); p. 2959; Justus Liebigs Annalen der Chemie; vol. 300; (1898); p. 268 View in Reaxys

adipate calcium

Rx-ID: 5929742 View in Reaxys 448/449 Yield

Conditions & References bei der Destillation Hentzschel; Wislicenus,J.; Justus Liebigs Annalen der Chemie; vol. 275; (1893); p. 313 View in Reaxys Wallach; Chemische Berichte; vol. 29; (1896); p. 2959; Justus Liebigs Annalen der Chemie; vol. 300; (1898); p. 268 View in Reaxys Wislicenus; Justus Liebigs Annalen der Chemie; vol. 275; (1893); p. 313 View in Reaxys O

N OH

ThO2

Rx-ID: 6682682 View in Reaxys 449/449 Yield

Conditions & References T= 350 °C , Das Adipinsaeurediamid Patent; I.G. Farbenind.; DE7439967 View in Reaxys

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