Valerophenone (1-Phenyl-1-pentanone) [C11H14O] by Asch

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344 reactions in Reaxys

2018-05-06 22h:01m:56s (UTC)

1. Query

Search as: Product, As drawn, No mixtures ) AND (IDE.XRN=1907717))

1/127

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Rx-ID: 281842 View in Reaxys 1/344 Yield 98 %

Conditions & References With Oxone, 3,3'-diiodo-2,2',6,6'-tetramethoxy-4,4'-biphenyldicarboxylic acid in nitromethane, water, Time= 11.5h, T= 30 - 35 °C Seth, Saona; Jhulki, Samik; Moorthy, Jarugu Narasimha; European Journal of Organic Chemistry; nb. 12; (2013); p. 2445 2452 View in Reaxys

95 %

With menthol, Dess-Martin periodane in dichloromethane, Time= 0.333333h, Dess-Martin oxidation Wang, Hua; Shuhler, Brian J.; Xian, Ming; Synlett; nb. 17; (2008); p. 2651 - 2654 View in Reaxys

94.2 %

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

94 %

8.14 : Example 8 Application of this method in the reaction of other alcohols to aldehydes and ketones The typical reaction steps are as follows:1 mmol of the starting alcohol of the reactant column shown in Table 2,OH - Ni3InLDH 14 mg,Mesitylene 5mL were added to the reactor,Into the oxygen,Atmospheric reaction,The reaction was stirred at 60 for a certain period of time.The solid catalyst was removed by filtration,Using gas chromatography internal standard method (chlorobenzene as internal standard) to analyze the content of liquid products,Calculate yield. With oxygen in 1,3,5-trimethyl-benzene, Time= 12h, T= 60 °C , p= 760.051Torr , Solvent, Reagent/catalyst Patent; Changzhou University; Zhou Weiyou; Dai Xuan; He Mingyang; Sun Fuan; Pan Jiugao; (8 pag.); CN107176898; (2017); (A) Chinese View in Reaxys

88 %

With oxovanadium(IV) sulfate, 4-nitrophenyl(phenyl)methanol, oxygen, magnesium sulfate, 4,4'-di-tert-butyl-2,2'- bipyridine in water, Time= 48h, T= 90 °C , p= 750.075Torr Kodama, Shintaro; Hashidate, Suguru; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya; Chemistry Letters; vol. 40; nb. 5; (2011); p. 495 - 497 View in Reaxys

86 %

Aerobic Oxidation of Benzylic Alcohols The oxidation of 1-phenyl-1-pentanol (1a) is representative (Table 2, entry 1): BMI-PF6 (85 mg, 0.30 mmol), 1-phenyl-1-pentanol (1a, 33 mg, 0.20 mmol), Cs2CO3 (33 mg, 0.10 mmol), and trifluoromethylbenzene (0.10 mL) were placed in a reaction flask with a reflux condenser and a drying tube lined with calcium chloride. The resulting mixture was stirred for 20 h at 105 °C. The reaction mixture was diluted with ethyl acetate and poured into water. The mixture was extracted with ethyl acetate three times. The combined organic layer was dried over Na2SO4, filtered through a pad of neutral alumina, and concentrated under reduced pressure. Purification by column chromatography on silica gel with hexane/ethyl acetate (10:1, v/v) as an eluent afforded 1-phenyl-1-pentanone (2a, 28 mg, 0.17 mmol) in 86percent yield. With oxygen, caesium carbonate in α,α,α-trifluorotoluene, Time= 20h, T= 105 °C , Air atmosphere, Ionic liquid Oda, Yoshiro; Hirano, Koji; Satoh, Tetsuya; Kuwabata, Susumu; Miura, Masahiro; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5392 - 5394 View in Reaxys

85 %

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

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View in Reaxys 83 %

4.6 Oxidation of alcohols under open-air atmosphere General procedure: VOSO4·5H2O (126.5 mg, 0.5 mmol), 4,4α-di-tert-butyl-2,2α-bipyridyl (268.4 mg, 1 mmol), and p-nitrobenzhydrol (229.3 mg, 0.05 mmol) were placed in a 100 mL round-bottomed flask, and then water (50 mL) was added. Next, the mixture was stirred, and then anhydrous MgSO4 (18.06 g, 150 mmol) was slowly added into the mixture (cooling by ice water). After that, substrate (10 mmol) was added into the mixture at room temperature, and the mixture was stirred at 90 °C for the appropriate time under open-air atmosphere. After the reaction, the mixture was extracted with ethyl acetate and dried over anhydrous MgSO4. The extracts were concentrated in vacuo. Purification of the products was carried out by silica gel column chromatography using hexane and diethyl ether as eluent to afford the analytically pure ketones. In Table 7 (entries 3, 7, and 8), crude products were purified by recrystallization with ethyl acetate in refrigerator, afforded analytically pure ketones. The product was identified by comparison with the commercially available sample using 1H NMR spectroscopy. With magnesium sulphate, vanadyl(IV) sulphate pentahydrate, 4-nitrophenyl(phenyl)methanol, 4,4'-di-tert-butyl-2,2'- bipyridine in water, Time= 120h, T= 0 - 90 °C , p= 750.075Torr Marui, Kuniaki; Higashiura, Yuuki; Kodama, Shintaro; Hashidate, Suguru; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya; Tetrahedron; vol. 70; nb. 14; (2014); p. 2431 - 2438 View in Reaxys

81 %

With sulfuric acid, dihydrogen peroxide, vanadia, benzyltriethylammonium bromide in water, Time= 1.5h, pH= 4, Heating Li, Chunbao; Zheng, Pengwu; Li, Jie; Zhang, Hang; Cui, Yi; Shao, Qiyun; Ji, Xiujie; Zhang, Jian; Zhao, Pengying; Xu, Yanli; Angewandte Chemie - International Edition; vol. 42; nb. 41; (2003); p. 5063 - 5066 View in Reaxys

81 %

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

63 %

With anionic TEMPO in water, T= 20 °C , Electrochemical reaction Mitsudo, Koichi; Kumagai, Hiroki; Takabatake, Fumiko; Kubota, Jun; Tanaka, Hideo; Tetrahedron Letters; vol. 48; nb. 51; (2007); p. 8994 - 8997 View in Reaxys With chloroform, dinitrogen tetraoxide Grundy; Journal of the Chemical Society; (1957); p. 5087 View in Reaxys With potassium hydroxide, potassium permanganate, acetone Adams; VanderWerf; Journal of the American Chemical Society; vol. 72; (1950); p. 4368,4371 View in Reaxys

12 % Chromat.

Time= 168h, T= 30 °C , by Corynebacterium equi IFO 3730 Ohta, Hiromichi; Yamada, Hiroshi; Tsuchihashi, Gen-ichi; Agricultural and Biological Chemistry; vol. 49; nb. 8; (1985); p. 2459 - 2462 View in Reaxys With 2,6-dichloropyridine N-oxide, trifluoromethylcyclohexane, polymer-supported Ru(CO)-porphyrin in hexane, benzene, Time= 0.25h, T= 55 °C Burri, Estelle; Leeder, Shannon M.; Severin, Kay; Gagne, Michel R.; Advanced Synthesis and Catalysis; vol. 348; nb. 12-13; (2006); p. 1640 - 1644 View in Reaxys With (R,R)-1,2-diphenylethylenediamine, potassium tert-butylate, cyclohexanone, dichloro(benzene)ruthenium(II) dimer, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in tetrahydrofuran, Time= 20h, T= 60 °C Adair, Gareth R. A.; Williams, Jonathan M. J.; Chemical Communications; nb. 25; (2007); p. 2608 - 2609 View in Reaxys

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With ketoreductase, acetone in phosphate buffer, pentane, T= 24.99 °C , pH= 7.3, Equilibrium constant, Further Variations: Solvents Tewari, Yadu B.; Kishore, Nand; Rozzell, J. David; Vanderah, David J.; Schantz, Michele M.; Journal of Chemical Thermodynamics; vol. 38; nb. 10; (2006); p. 1165 - 1171 View in Reaxys With 10 Ru/C, oxygen in toluene, Time= 24h, T= 70 °C , p= 760.051Torr Mori, Shigeki; Takubo, Masato; Makida, Kazuya; Yanase, Takayoshi; Aoyagi, Satoka; Maegawa, Tomohiro; Monguchi, Yasunari; Sajiki, Hironao; Chemical Communications; nb. 34; (2009); p. 5159 - 5161 View in Reaxys With sodium dichromate, sulfuric acid in dimethyl sulfoxide Chang, Lu; Kuang, Yulong; Qin, Bo; Zhou, Xin; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Organic Letters; vol. 12; nb. 10; (2010); p. 2214 - 2217 View in Reaxys With Pd/TiO2(at)MIL-101, Time= 48h, T= 90 °C , Inert atmosphere Tilgner, Dominic; Friedrich, Martin; Hermannsdörfer, Justus; Kempe, Rhett; ChemCatChem; vol. 7; nb. 23; (2015); p. 3916 - 3922 View in Reaxys With oxygen in toluene, Time= 8h, T= 80 °C Sun, Fuan; Zhou, Jiacheng; Zhou, Weiyou; Pan, Jiugao; Qian, Junfeng; He, Mingyang; Chen, Qun; New Journal of Chemistry; vol. 42; nb. 6; (2018); p. 4029 - 4035 View in Reaxys

Rx-ID: 40836230 View in Reaxys 2/344 Yield

Conditions & References With silver tetrafluoroborate, 1,3-di(2,6-diisopropylphenyl)-4,5-diundecylimidazolium bromide, water, sodium dodecyl-sulfate, Time= 24h, T= 50 °C , Inert atmosphere, Overall yield = 78 percent; Overall yield = 63 mg Rühling, Andreas; Galla, Hans-Joachim; Glorius, Frank; Chemistry - A European Journal; vol. 21; nb. 35; (2015); p. 12291 - 12294 View in Reaxys

16 Stage 1: in water, toluene, Time= 0.0833333h, T= 20 °C , Inert atmosphere %Spectr., Stage 2: With silver trifluoromethanesulfonate in water, toluene, Time= 1h, T= 50 °C , Inert atmosphere, regioselective reaction 33 %Spectr. Endo, Naoki; Inoue, Mami; Iwasawa, Tetsuo; European Journal of Organic Chemistry; vol. 2018; nb. 9; (2018); p. 1136 1140 View in Reaxys

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Rx-ID: 40980169 View in Reaxys 3/344 Yield 89 %

Conditions & References With caesium carbonate in 1,4-dioxane, Time= 8h, Reflux, Reagent/catalyst, Solvent Hu, Yu Lin; Wu, Ya Pan; Lu, Ming; Applied Organometallic Chemistry; vol. 32; nb. 2; (2018); Art.No: E4096 View in Reaxys

79 %

2.7 Catalytic activity of 1a and 1b in acylation reaction General procedure: Aryl halides (2mmol) and aldehydes (2.4mmol) in 1, 4 - dioxane (20cm3) were mixed together. The base cesium carbonate (6mmol) and the respective catalyst (0.004mmol) in dichloromethane (5cm3) were then added to the solution and stirred at 100°C. The reactions were monitored by TLC and the products were isolated by silica gel column chromatography using ethyl acetate and hexane as eluents. The products were characterized by 1H NMR, 13C NMR and melting point determination followed by their comparison with the standard literature data. With C20H19Cl2PPdS, caesium carbonate in 1,4-dioxane, dichloromethane, Time= 16h, T= 100 °C , Catalytic behavior, Reagent/ catalyst, Solvent Saikia, Kokil; Dutta, Dipak Kumar; Journal of Molecular Catalysis A: Chemical; vol. 408; (2015); p. 20 - 25; Art.No: 9557 View in Reaxys

Rx-ID: 40980173 View in Reaxys 4/344 Yield 86 %

Conditions & References With caesium carbonate in 1,4-dioxane, Time= 10h, Reflux Hu, Yu Lin; Wu, Ya Pan; Lu, Ming; Applied Organometallic Chemistry; vol. 32; nb. 2; (2018); Art.No: E4096 View in Reaxys

74 %

2.7 Catalytic activity of 1a and 1b in acylation reaction General procedure: Aryl halides (2mmol) and aldehydes (2.4mmol) in 1, 4 - dioxane (20cm3) were mixed together. The base cesium carbonate (6mmol) and the respective catalyst (0.004mmol) in dichloromethane (5cm3) were then added to the solution and stirred at 100°C. The reactions were monitored by TLC and the products were isolated by silica gel column chromatography using ethyl acetate and hexane as eluents. The products were characterized by 1H NMR, 13C NMR and melting point determination followed by their comparison with the standard literature data. With C20H19Cl2PPdS, caesium carbonate in 1,4-dioxane, dichloromethane, Time= 16h, T= 100 °C , Reagent/catalyst Saikia, Kokil; Dutta, Dipak Kumar; Journal of Molecular Catalysis A: Chemical; vol. 408; (2015); p. 20 - 25; Art.No: 9557 View in Reaxys

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Rx-ID: 47181177 View in Reaxys 5/344 Yield 74 %

Conditions & References With caesium carbonate in 1,4-dioxane, Time= 14h, Reflux Hu, Yu Lin; Wu, Ya Pan; Lu, Ming; Applied Organometallic Chemistry; vol. 32; nb. 2; (2018); Art.No: E4096 View in Reaxys

Rx-ID: 47197800 View in Reaxys 6/344 Yield

Conditions & References Reaction Steps: 2 1: glycerol / 20 °C / Green chemistry 2: hydrogenchloride; water / glycerol / 0.5 h / 100 °C With hydrogenchloride, water in glycerol Rodríguez-Álvarez, María J.; García-Álvarez, Joaquín; Uzelac, Marina; Fairley, Michael; O'Hara, Charles T.; Hevia, Eva; Chemistry - A European Journal; vol. 24; nb. 7; (2018); p. 1720 - 1725 View in Reaxys

Rx-ID: 47197832 View in Reaxys 7/344 Yield

Conditions & References With hydrogenchloride, water in glycerol, Time= 0.5h, T= 100 °C Rodríguez-Álvarez, María J.; García-Álvarez, Joaquín; Uzelac, Marina; Fairley, Michael; O'Hara, Charles T.; Hevia, Eva; Chemistry - A European Journal; vol. 24; nb. 7; (2018); p. 1720 - 1725 View in Reaxys

Rx-ID: 45950880 View in Reaxys 8/344

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Yield

Conditions & References

30 %, 70 %

With water in hexane, cyclohexane, Time= 0.0166667h, T= 20 °C Dilauro, Giuseppe; Dell'Aera, Marzia; Vitale, Paola; Capriati, Vito; Perna, Filippo Maria; Angewandte Chemie - International Edition; vol. 56; nb. 34; (2017); p. 10200 - 10203; Angew. Chem.; vol. 129; nb. 34; (2017); p. 10334 - 10337,4 View in Reaxys

Cl Mg

H 2N

Rx-ID: 45950881 View in Reaxys 9/344 Yield 20 %, 80 %

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

HO O

Rx-ID: 11134753 View in Reaxys 10/344 Yield 68 %

Conditions & References With nickel in tetrahydrofuran, Time= 2h, T= 76 °C Alonso, Francisco; Riente, Paola; Yus, Miguel; Synlett; nb. 12; (2007); p. 1877 - 1880 View in Reaxys

68 %

With nickel(0) nanoparticles in tetrahydrofuran, Time= 2h, T= 76 °C , Inert atmosphere Alonso, Francisco; Riente, Paola; Yus, Miguel; European Journal of Organic Chemistry; nb. 29; (2008); p. 4908 - 4914 View in Reaxys

48 %

Typical procedure for the synthesis of 4a General procedure: A solution of catalyst 1 (2 mol percent, 0.01 mmol), acetophenone (1.0 mmol), benzyl alcohol (1.2 mmol), cesium carbonate (1.5 mmol), and xylene (3 mL) were stirred in a Schlenk tube in N2 atmosphere. The mixture was heated under reflux for 24 h and then cooled to room temperature. The resulting solution was directly purified by column chromatography with petroleum ether/ethyl acetate (10 : 1) as eluent to give the desired product. With P,P'-1,2-bis(diphenylphosphino)ethane(P,N-diphenyl(o-N-methylanilido)phosphine)rhodium(I), caesium carbonate in 5,5dimethyl-1,3-cyclohexadiene, Time= 24h, Inert atmosphere, Schlenk technique Yu; Wang; Wu; Russian Journal of General Chemistry; vol. 86; nb. 1; (2016); p. 178 - 183; Zh. Obshch. Khim. View in Reaxys

42 %

Typicalprocedure for the synthesis of 5a

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General procedure: Catalyst 2b (1 molpercent, 0.01 mmol), benzylalcohol (1.1 mmol), acetophenone (1.0 mmol), Cesiumcarbonate (1.0 mmol), and tert-amyl alcohol (2 mL) was added toa Schlenk tube under N2 atmosphere. The mixture was heated under 120oC for 24 h and then cooled to room temperature. Theresulting solution was directly purified by columnchromatography with petroleum ether/ethyl acetate (10:1) as eluent to give 1,3-diphenylpropan-1-one (5a) as awhite solid. With C38H43IrN2PS2 (1+)*CF3O3S(1-), caesium carbonate in tert-Amyl alcohol, Time= 24h, T= 120 °C , Schlenk technique, Inert atmosphere Wang, Dawei; Zhao, Keyan; Ma, Piming; Xu, Chongying; Ding, Yuqiang; Tetrahedron Letters; vol. 55; nb. 52; (2014); p. 7233 - 7235 View in Reaxys

(v2)

Rx-ID: 11243520 View in Reaxys 11/344 Yield 76 %

Conditions & References With tributylphosphine in tetrahydrofuran, Time= 0.333333h, T= 20 °C , Kinetics, Temperature, Concentration, Time Ömür Pekel, Özgen; Journal of Physical Organic Chemistry; vol. 29; nb. 4; (2016); p. 190 - 195 View in Reaxys

97 % Chromat.

Stage 1: With copper(l) iodide in tetrahydrofuran, Time= 0.25h, T= -20 °C Stage 2: in tetrahydrofuran, diethylene glycol dimethyl ether, Time= 0.333333h, T= 20 °C , Further stages. Erdik, Ender; Pekel, Oezgen Oemuer; Journal of Organometallic Chemistry; vol. 693; nb. 2; (2008); p. 338 - 342 View in Reaxys

90 %Chromat.

With copper(l) iodide in tetrahydrofuran, Time= 0.333333h, T= 25 °C , Inert atmosphere, Solvent Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.; Journal of Organometallic Chemistry; vol. 745-746; (2013); p. 235 - 241 View in Reaxys

(v2)

Rx-ID: 11243522 View in Reaxys 12/344 Yield 77 %

Conditions & References With tributylphosphine in tetrahydrofuran, Time= 1h, T= 20 °C , Inert atmosphere, chemoselective reaction Erdik, Ender; Pekel, Oezgen Oemuer; Tetrahedron Letters; vol. 50; nb. 13; (2009); p. 1501 - 1503 View in Reaxys

82 % Chromat.

Stage 1: With copper(l) iodide in tetrahydrofuran, Time= 0.25h, T= -20 °C Stage 2: With tri n-butyl phosphine in tetrahydrofuran, Time= 0.333333h, T= 20 °C , Further stages. Erdik, Ender; Pekel, Oezgen Oemuer; Journal of Organometallic Chemistry; vol. 693; nb. 2; (2008); p. 338 - 342 View in Reaxys With tributylphosphine in tetrahydrofuran, T= 0 °C , Kinetics, Concentration

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Ömür Pekel, Özgen; Journal of Physical Organic Chemistry; vol. 29; nb. 4; (2016); p. 190 - 195 View in Reaxys

HO HO

Rx-ID: 41983764 View in Reaxys 13/344 Yield 42 %

Conditions & References Typical procedure for the synthesis of 4a General procedure: A solution of catalyst 1 (2 mol percent, 0.01 mmol), acetophenone (1.0 mmol), benzyl alcohol (1.2 mmol), cesium carbonate (1.5 mmol), and xylene (3 mL) were stirred in a Schlenk tube in N2 atmosphere. The mixture was heated under reflux for 24 h and then cooled to room temperature. The resulting solution was directly purified by column chromatography with petroleum ether/ethyl acetate (10 : 1) as eluent to give the desired product. With P,P'-1,2-bis(diphenylphosphino)ethane(P,N-diphenyl(o-N-methylanilido)phosphine)rhodium(I), caesium carbonate in 5,5dimethyl-1,3-cyclohexadiene, Time= 24h, Inert atmosphere, Schlenk technique Yu; Wang; Wu; Russian Journal of General Chemistry; vol. 86; nb. 1; (2016); p. 178 - 183; Zh. Obshch. Khim. View in Reaxys

31 %

With C38H43IrN2PS2 (1+)*CF3O3S(1-), caesium carbonate in toluene, Time= 16h, T= 110 °C , Inert atmosphere Wang, Dawei; Zhao, Keyan; Yu, Xin; Miao, Hongyan; Ding, Yuqiang; RSC Advances; vol. 4; nb. 81; (2014); p. 42924 42929 View in Reaxys

(v2)

Rx-ID: 42447611 View in Reaxys 14/344 Yield

Conditions & References With tributylphosphine in tetrahydrofuran, T= 0 °C , Kinetics Ömür Pekel, Özgen; Journal of Physical Organic Chemistry; vol. 29; nb. 4; (2016); p. 190 - 195 View in Reaxys

(v2)

Rx-ID: 42447612 View in Reaxys 15/344 Yield

Conditions & References With tributylphosphine in tetrahydrofuran, T= 0 °C , Kinetics Ömür Pekel, Özgen; Journal of Physical Organic Chemistry; vol. 29; nb. 4; (2016); p. 190 - 195

9/127

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View in Reaxys

(v2)

Rx-ID: 42447614 View in Reaxys 16/344 Yield

Conditions & References With tributylphosphine in tetrahydrofuran, T= 0 °C , Kinetics Ömür Pekel, Özgen; Journal of Physical Organic Chemistry; vol. 29; nb. 4; (2016); p. 190 - 195 View in Reaxys

(v2)

Rx-ID: 42447615 View in Reaxys 17/344 Yield

Conditions & References With tributylphosphine in tetrahydrofuran, T= 0 °C , Kinetics Ömür Pekel, Özgen; Journal of Physical Organic Chemistry; vol. 29; nb. 4; (2016); p. 190 - 195 View in Reaxys

(v2)

Rx-ID: 42447616 View in Reaxys 18/344 Yield

Conditions & References With tributylphosphine in tetrahydrofuran, T= 0 °C , Kinetics Ömür Pekel, Özgen; Journal of Physical Organic Chemistry; vol. 29; nb. 4; (2016); p. 190 - 195 View in Reaxys O

10/127

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Rx-ID: 42527768 View in Reaxys 19/344 Yield

Conditions & References

66 %Chromat., 34 %Chromat.

Stage 1:Time= 1h, T= 0 °C Stage 2: With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride in toluene, Time= 12h, T= 80 °C , Reagent/catalyst, Solvent Wolters, Alexander T.; Hornillos, Valentin; Heijnen, Dorus; Giannerini, Massimo; Feringa, Ben L.; ACS Catalysis; vol. 6; nb. 4; (2016); p. 2622 - 2625 View in Reaxys O

O N

Rx-ID: 42527770 View in Reaxys 20/344 Yield 51 %Chromat., 32 %Chromat., 17 %Chromat.

Conditions & References Stage 1:Time= 1h, T= 0 °C Stage 2: With tris-(dibenzylideneacetone)dipalladium(0), XPhos in toluene, Time= 12h, T= 80 °C , Reagent/catalyst, Solvent Wolters, Alexander T.; Hornillos, Valentin; Heijnen, Dorus; Giannerini, Massimo; Feringa, Ben L.; ACS Catalysis; vol. 6; nb. 4; (2016); p. 2622 - 2625 View in Reaxys

Rx-ID: 42571922 View in Reaxys 21/344 Yield 82%

Conditions & References in tetrahydrofuran, hexane, Time= 0.25h, T= -78 °C , Schlenk technique, Inert atmosphere, chemoselective reaction Liu, Chengwei; Achtenhagen, Marcel; Szostak, Michal; Organic Letters; vol. 18; nb. 10; (2016); p. 2375 - 2378 View in Reaxys

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Rx-ID: 42571966 View in Reaxys 22/344 Yield

Conditions & References Reaction Steps: 2 1: potassium carbonate / diethyl ether; water / 0.25 h / -78 - 0 °C / Inert atmosphere 2: tetrahydrofuran; hexane / 0.25 h / -78 °C / Schlenk technique; Inert atmosphere With potassium carbonate in tetrahydrofuran, diethyl ether, hexane, water Liu, Chengwei; Achtenhagen, Marcel; Szostak, Michal; Organic Letters; vol. 18; nb. 10; (2016); p. 2375 - 2378 View in Reaxys

O O

Rx-ID: 43710996 View in Reaxys 23/344 Yield 86 %

Conditions & References Stage 1: in tetrahydrofuran, Time= 0.25h, T= 0 °C , Weinreb Ketone Synthesis Stage 2: in tetrahydrofuran, hexane, Time= 0.333333h, T= -78 °C , Weinreb Ketone Synthesis Nugent, Jeremy; Schwartz, Brett D.; Organic Letters; vol. 18; nb. 15; (2016); p. 3834 - 3837 View in Reaxys

Rx-ID: 649552 View in Reaxys 24/344 Yield 90 %

Conditions & References Stage 1: With aluminum (III) chloride in 1,2-dichloro-ethane, Time= 0.166667h, T= 0 °C , Friedel-Crafts Acylation Stage 2: in 1,2-dichloro-ethane, Time= 2h, T= 50 °C , Friedel-Crafts Acylation Siddaraju, Yogesh; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 13; nb. 24; (2015); p. 6749 6753 View in Reaxys With aluminium trichloride Layraud; Bulletin de la Societe Chimique de France; vol. <3> 35; (1906); p. 233 View in Reaxys With aluminum (III) chloride Zygadlo; Dardas; Nowicka; Hofmann; Galewski; Molecular Crystals and Liquid Crystals; vol. 509; nb. 1; (2009); p. 283 291

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View in Reaxys Stage 1: With aluminum (III) chloride in 1,2-dichloro-ethane, Time= 0.166667h, T= 0 °C Stage 2: in 1,2-dichloro-ethane, Time= 2h, T= 0 - 50 °C Siddaraju, Yogesh; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 13; nb. 48; (2015); p. 11651 11656 View in Reaxys

Rx-ID: 39583797 View in Reaxys 25/344 Yield

Conditions & References

62 %

With palladium (II) trifluoroacetate, sodium anthraquinone-2-sulfonate, oxygen, magnesium sulfate in chlorobenzene, Time= 24h, T= 110 °C , p= 760.051Torr , Sealed tube Iosub, Andrei V.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 137; nb. 10; (2015); p. 3454 - 3457 View in Reaxys

Rx-ID: 39583809 View in Reaxys 26/344 Yield

Conditions & References Reaction Steps: 3 1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: tetrahydrofuran / 2 h / 0 °C 3.1: palladium (II) trifluoroacetate; sodium anthraquinone-2-sulfonate; oxygen; magnesium sulfate / chlorobenzene / 24 h / 110 °C / 760.05 Torr / Sealed tube With dmap, palladium (II) trifluoroacetate, sodium anthraquinone-2-sulfonate, oxygen, magnesium sulfate, 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in tetrahydrofuran, dichloromethane, chlorobenzene Iosub, Andrei V.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 137; nb. 10; (2015); p. 3454 - 3457 View in Reaxys

O O N

Rx-ID: 39583831 View in Reaxys 27/344 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 2 h / 0 °C

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2: palladium (II) trifluoroacetate; sodium anthraquinone-2-sulfonate; oxygen; magnesium sulfate / chlorobenzene / 24 h / 110 °C / 760.05 Torr / Sealed tube With palladium (II) trifluoroacetate, sodium anthraquinone-2-sulfonate, oxygen, magnesium sulfate in tetrahydrofuran, chlorobenzene Iosub, Andrei V.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 137; nb. 10; (2015); p. 3454 - 3457 View in Reaxys

N H

Rx-ID: 40116710 View in Reaxys 28/344 Yield 63 %, 60 %

Conditions & References 13 : 4.2. General procedure for the direct transformation of tertiary amides into ketones and amines General procedure: Tf2O (1.2 equiv) was added dropwise to a cooled (−78 °C) solution of amide 5 (1.0 equiv) and DTBMP (1.2 equiv) in CH2Cl2 (5 mL). The reaction was allowed warming to 0 °C over 2 h. A solution of Grignard reagent (1.0 equiv) in Et2O was added dropwise to the resultant mixture at −78 °C, and the mixture was stirred at the same temperature for 2 h. The reaction mixture was then quenched with an aqueous solution of 15percent HCl (5 mL). The organic layer was separated and the aqueous phase was extracted with diethyl ether (3×5 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the desired ketone 1. To isolate the corresponding amine, the aqueous solution layer was basified with an aqueous solution of 15percent NaOH (6 mL), and extracted with dichloromethane (3×10 mL), the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the desired amine 6. Stage 1: With 2,6-di-tert-butyl-4-methylpyridine, trifluoromethylsulfonic anhydride in dichloromethane, Time= 2h, T= -78 - 0 °C , Inert atmosphere Stage 2: in diethyl ether, dichloromethane, Time= 2h, T= -78 °C , Inert atmosphere, chemoselective reaction Huang, Pei-Qiang; Wang, Yu; Xiao, Kai-Jiong; Huang, Ying-Hong; Tetrahedron; vol. 71; nb. 24; (2015); p. 4248 - 4254; Art.No: 26677 View in Reaxys

B O O

Rx-ID: 40120962 View in Reaxys 29/344 Yield 79 %

Conditions & References With bis(1,5-cyclooctadiene)nickel (0), 1,3-bis{2,6-bis(diphenylmethyl)-4-methylphenyl}-imidazolin-2-ylidene, Hexafluoroacetone in tetrahydrofuran, Time= 10h, T= 40 °C , Schlenk technique, Inert atmosphere

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Gu, Li-Jun; Jin, Cheng; Zhang, Hong-Tao; Chemistry - A European Journal; vol. 21; nb. 24; (2015); p. 8741 - 8744 View in Reaxys

CH –2

Li+

Zn 2+ O

Rx-ID: 40683040 View in Reaxys 30/344 Yield

Conditions & References

71 %

Stage 1: With methyllithium in tetrahydrofuran, diethyl ether, Time= 1h, T= -78 °C , Schlenk technique, Inert atmosphere Stage 2: in 1,4-dioxane, Time= 18h, T= 50 °C , Schlenk technique, Inert atmosphere, chemoselective reaction Murata, Ryo; Hirano, Keiichi; Uchiyama, Masanobu; Chemistry - An Asian Journal; vol. 10; nb. 6; (2015); p. 1286 - 1290 View in Reaxys

(v5) (v5)(v5)(v5) C– (v4) 3+ – W N(v10) (v5) H C– H (v5) (v4)

(v1)

Rx-ID: 41003167 View in Reaxys 31/344 Yield 27 %, 27 %

Conditions & References Time= 18h, T= 80 °C , p= 39547.2Torr , Glovebox Baillie, Rhett A.; Lefvre, Guillaume P.; Wakeham, Russell J.; Holmes, Aaron S.; Legzdins, Peter; Organometallics; vol. 34; nb. 16; (2015); p. 4085 - 4092 View in Reaxys

Br Zn (v2)

Rx-ID: 41381636 View in Reaxys 32/344 Yield 62 %

Conditions & References With bis(1,5-cyclooctadiene)nickel(0), 4'-methoxy-2,2,2-trifluoroacetophenone, 1-iodo-propane, magnesium chloride in tetrahydrofuran, 1,4-dioxane, Time= 8h, T= 30 - 40 °C , Inert atmosphere Jin, Cheng; Gu, Lijun; Yuan, Minglong; Catalysis Science and Technology; vol. 5; nb. 9; (2015); p. 4341 - 4345 View in Reaxys

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O O N Li

Rx-ID: 1673456 View in Reaxys 33/344 Yield 84 %

Conditions & References in tetrahydrofuran, Time= 1h, T= 0 °C Nahm, Steven; Weinreb, Steven M.; Tetrahedron Letters; vol. 22; nb. 39; (1981); p. 3815 - 3818 View in Reaxys

84 %

With 1-Phenylprop-1-yne, titanium(IV) isopropylate in tetrahydrofuran, Time= 3h, T= 20 °C , Inert atmosphere, Catalytic behavior, regioselective reaction Silwal, Sajan; Rahaim, Ronald J.; Journal of Organic Chemistry; vol. 79; nb. 17; (2014); p. 8469 - 8476 View in Reaxys

51 %

in tetrahydrofuran, T= -40 °C Kumar, Amit; Akula, Hari Kiran; Lakshman, Mahesh K.; European Journal of Organic Chemistry; nb. 14; (2010); p. 2709 2715 View in Reaxys Stage 1: in tetrahydrofuran, Time= 1h, T= 0 °C Stage 2: With acetic acid in tetrahydrofuran, methanol, water, T= 0 °C , Further stages. Jackson, Mary M.; Leverett, Carolyn; Toczko, Jennifer F.; Roberts, John C.; Journal of Organic Chemistry; vol. 67; nb. 14; (2002); p. 5032 - 5035 View in Reaxys

Rx-ID: 4162431 View in Reaxys 34/344 Yield 64 %

Conditions & References With 2,2'-azobis(isobutyronitrile), oxygen in nitromethane, Time= 12h, T= 60 °C , Schlenk technique Wang, Guang-Zu; Li, Xing-Long; Dai, Jian-Jun; Xu, Hua-Jian; Journal of Organic Chemistry; vol. 79; nb. 15; (2014); p. 7220 - 7225 View in Reaxys With Et3SiOOOH in dichloromethane, T= -78 °C Posner, Gary H.; Webb, Kevin S.; Nelson, William M.; Kishimoto, Takashi; Seliger, Howard H.; Journal of Organic Chemistry; vol. 54; nb. 14; (1989); p. 3252 - 3254 View in Reaxys

60 %Chromat.

With N -hydroxyphthalimide, oxygen in N,N-dimethyl acetamide, water, Time= 62h, T= 100 °C Lin, Riyuan; Chen, Feng; Jiao, Ning; Organic Letters; vol. 14; nb. 16; (2012); p. 4158 - 4161 View in Reaxys

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Rx-ID: 8940554 View in Reaxys 35/344 Yield 11 % Chromat.

Conditions & References With Sphingomonas paucimobilis NCIMB 8195 in water, N,N-dimethyl-formamide, Time= 120h, Title compound not separated from byproducts Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys With lyophilized cells of Rhodococcus ruber DSM 44541, acetone in phosphate buffer, Time= 24h, T= 24 °C , pH= 8.0, Title compound not separated from byproducts Stampfer, Wolfgang; Kosjek, Birgit; Faber, Kurt; Kroutil, Wolfgang; Journal of Organic Chemistry; vol. 68; nb. 2; (2003); p. 402 - 406 View in Reaxys With sodium isopropylate, acetone, [RuCl2(PPh3)(ferrocenyloxazolinylphosphine)] in isopropyl alcohol, Time= 0.5h, T= 50 °C Nishibayashi, Yoshiaki; Yamauchi, Akiyoshi; Onodera, Gen; Uemura, Sakae; Journal of Organic Chemistry; vol. 68; nb. 15; (2003); p. 5875 - 5880 View in Reaxys Stage 1: With MnIII(L-5-t-Bu)(Cl), 1-butyl-2,6-dimethyl-pyridinium; bromide in dichloromethane, water, T= 20 °C Stage 2: With [bis(acetoxy)iodo]benzene in dichloromethane, water, Time= 0.1h, T= 20 °C Cheng, Qigan; Deng, Fanguo; Xia, Chungu; Sun, Wei; Tetrahedron Asymmetry; vol. 19; nb. 20; (2008); p. 2359 - 2362 View in Reaxys 2.2. Catalytic procedure. General procedure: In a typical process, a mixture of (±)-1-phenylethanol (0.122 g, 1 mmol), chiral Mn(III)-salen complex (0.0127 g, 2 molpercent), Br2 (4.1 μL, 8 molpercent), KOAC (0.1962 g, 2 mmol), CH2Cl2 (2.0 mL), and water (4.0 mL) was magnetically stirred in a 10-mL two-necked flask at 20 °C. The oxidant NaClO (0.289 g, 0.80 mmol) was then added slowly within 40 min, and the reaction was monitored by GC/HPLC equipped with a suitable chiral column. With sodium hypochlorite, C38H56ClMnN2O2, bromine, potassium acetate in dichloromethane, water, Time= 0.666667h, T= 20 °C , Kinetics, Mechanism, enantioselective reaction Zhang, Yuecheng; Zhou, Qiao; Ma, Wenchan; Zhao, Jiquan; Catalysis Communications; vol. 45; (2014); p. 114 - 117 View in Reaxys

O O

Cl (v3)

Cu Zn (v2)

Rx-ID: 37261868 View in Reaxys 36/344 Yield

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While carrying out the pseudo-first order kinetic experiments, the volume of the reaction mixture was kept constant in order to keep the concentration of benzoyl chloride 2 constant. The mixture was quickly thermostated by immersing the flask cooling bath at constant temperature on a magnetic stirrer. Aliquots (10-16) were withdrawn from the mixture by syringe under nitrogen atmosphere at 5 or 5 min intervals and were hydrolyzed in a vial containing saturated NH4Cl solution containing 20percent NH3. The aqueous phase was extracted with ether and the ethereal phase was analyzed by GC. The rate data were collected by measuring the concentration of coupling products 3a and 3b in each sample. Self consistent data could be obtained for two-four half lives. Reproducibility of the rate constants was generally +/-5-10percent which is in the error limit of GC analysis. in tetrahydrofuran, T= 0 °C , Inert atmosphere, Kinetics, Concentration, Temperature Pekel, Oezgen Oemuer; Erdik, Ender; Journal of Organometallic Chemistry; vol. 751; (2014); p. 644 - 653 View in Reaxys

O O

Cl (v3)

Cu Zn (v2)

Rx-ID: 37261869 View in Reaxys 37/344 Yield

Conditions & References A typical kinetic procedure for reaction of n-BuPhCuZnI 1ab with benzoyl chloride 2 in THF at -15 °C under pseudofirst order conditions in the presence of excess 1ab General procedure: In a flame-dried, two-necked flasks with septum caps and stirring bars, n-BuPhCuZnI 1ab (10 mmol) was prepared using THF solution of ZnCl2 (10 mmol), PhMgBr (10 mmol) in THF, n-BuMgBr(10 mmol) in THF and CuI (10 mmol) at 15 °C as explained above.To the stirred mixture, internal standard nonane (1 mmol) and PhCOCl 2 (1 mmol) was added. While carrying out the pseudo-first order kinetic experiments, the volume of the reaction mixture was kept constant in order to keep the concentration of benzoyl chloride 2 constant. The mixture was quickly thermostated by immersing the flask cooling bath at constant temperature on a magnetic stirrer. Aliquots (10-16) were withdrawn from the mixture by syringe under nitrogen atmosphere at 5 or 5 min intervals and were hydrolyzed in a vial containing saturated NH4Cl solution containing 20percent NH3. The aqueous phase was extracted with ether and the ethereal phase was analyzed by GC. The rate data were collected by measuring the concentration of coupling products 3a and 3b in each sample. Self consistent data could be obtained for two-four half lives. Reproducibility of the rate constants was generally +/-5-10percent which is in the error limit of GC analysis. in tetrahydrofuran, T= 0 °C , Inert atmosphere, Kinetics Pekel, Oezgen Oemuer; Erdik, Ender; Journal of Organometallic Chemistry; vol. 751; (2014); p. 644 - 653 View in Reaxys

O O

Cl (v3)

Cu Zn (v2)

Rx-ID: 37261870 View in Reaxys 38/344 Yield

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The aqueous phase was extracted with ether and the ethereal phase was analyzed by GC. The rate data were collected by measuring the concentration of coupling products 3a and 3b in each sample. Self consistent data could be obtained for two-four half lives. Reproducibility of the rate constants was generally +/-5-10percent which is in the error limit of GC analysis. in tetrahydrofuran, T= 0 °C , Inert atmosphere, Kinetics Pekel, Oezgen Oemuer; Erdik, Ender; Journal of Organometallic Chemistry; vol. 751; (2014); p. 644 - 653 View in Reaxys

O O O

O O

Cu (v3)

Zn (v2)

Rx-ID: 37261871 View in Reaxys 39/344 Yield

O O

Cl (v3)

Cu Zn (v2)

Rx-ID: 37261872 View in Reaxys 40/344 Yield

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in tetrahydrofuran, T= 0 °C , Inert atmosphere, Kinetics Pekel, Oezgen Oemuer; Erdik, Ender; Journal of Organometallic Chemistry; vol. 751; (2014); p. 644 - 653 View in Reaxys

O O

Cl (v3)

O Br

Cu Zn (v2)

Rx-ID: 37261873 View in Reaxys 41/344 Yield

Cu (v3)

Zn (v2)

Rx-ID: 37261874 View in Reaxys 42/344 Yield

Conditions & References A typical kinetic procedure for reaction of n-BuPhCuZnI 1ab with benzoyl chloride 2 in THF at -15 °C under pseudofirst order conditions in the presence of excess 1ab General procedure: In a flame-dried, two-necked flasks with septum caps and stirring bars, n-BuPhCuZnI 1ab (10 mmol) was prepared using THF solution of ZnCl2 (10 mmol), PhMgBr (10 mmol) in THF, n-BuMgBr(10 mmol) in THF and CuI (10 mmol) at 15 °C as explained above.To the stirred mixture, internal standard nonane (1 mmol) and PhCOCl 2 (1 mmol) was added. While carrying out the pseudo-first order kinetic experiments, the volume of the reaction mixture was kept constant in order to keep the concentration of benzoyl chloride 2 constant. The mixture was quickly thermostated by immersing the flask cooling bath at constant temperature on a magnetic stirrer. Aliquots (10-16) were withdrawn from the mixture by syringe under nitrogen atmosphere at 5 or 5 min intervals and were hydrolyzed in a vial containing saturated NH4Cl solution containing 20percent NH3. The aqueous phase was extracted with ether and the ethereal phase was analyzed by GC. The rate data were collected by measuring the concentration of coupling products 3a and 3b in each sample. Self consistent data could be obtained for two-four half lives. Reproducibility of the rate constants was generally +/-5-10percent which is in the error limit of GC analysis. in tetrahydrofuran, T= -15 °C , Inert atmosphere, Kinetics, Concentration, Temperature Pekel, Oezgen Oemuer; Erdik, Ender; Journal of Organometallic Chemistry; vol. 751; (2014); p. 644 - 653 View in Reaxys

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O F

Rx-ID: 37507557 View in Reaxys 43/344 Yield 0.44 %, 88 %

Conditions & References With potassium fluoride, C94H134O4P2Pd2, silver fluoride in cyclohexane, Time= 14h, T= 110 °C , Sealed tube Lee, Hong Geun; Milner, Phillip J.; Buchwald, Stephen L.; Journal of the American Chemical Society; vol. 136; nb. 10; (2014); p. 3792 - 3795 View in Reaxys

O Li

Rx-ID: 38214707 View in Reaxys 44/344 Yield 92 %

Conditions & References 4.3 Synthesis of ketones from representative esters in a one-pot reaction (Table 3) General procedure: The following experimental procedure for the synthesis of 1-phenylpentanone is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.18mL, 2.1mmol) and 10mL THF. After cooling to 0°C, DIBALH (2.0mL, 1.0M in hexane, 2.0mmol) was added dropwise and stirred for 3h at same temperature. To a reaction mixture was slowly added ethyl benzoate (0.14g, 1.0mmol) and stirred for 10min. Then, n-BuLi (1.25mL, 1.6M in hexane, 2.0mmol) was added and the mixture was stirred for 10min again. The reaction was stopped by the aqueous 1N HCl (10mL) and extracted with diethyl ether (2×10mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded 1phenylpentanone (150mg, 92percent). Stage 1: With morpholine, diisobutylaluminium hydride in tetrahydrofuran, hexane, Time= 3.16667h, T= 0 °C , Inert atmosphere Stage 2: in tetrahydrofuran, hexane, Time= 0.166667h, T= 0 °C , Inert atmosphere Jeon, Ah Ram; Kim, Min Eai; Park, Jae Kyo; Shin, Won Kyu; An, Duk Keun; Tetrahedron; vol. 70; nb. 29; (2014); p. 4420 - 4424 View in Reaxys

Rx-ID: 38749067 View in Reaxys 45/344 Yield 92 %

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Wu, Jie; Yang, Xiaoqing; He, Zhi; Mao, Xianwen; Hatton, T. Alan; Jamison, Timothy F.; Angewandte Chemie - International Edition; vol. 53; nb. 32; (2014); p. 8416 - 8420; Angew. Chem.; vol. 126; nb. 32; (2014); p. 8556 - 8560,5 View in Reaxys

O HO

Rx-ID: 38749068 View in Reaxys 46/344 Yield

Conditions & References Stage 1: With tert.-butyl lithium in tetrahydrofuran, pentane, Time= 0.5h, T= -78 °C Stage 2: With [2,2]bipyridinyl, (-)-menthol in tetrahydrofuran, pentane, Inert atmosphere Stage 3:Reagent/catalyst, Further stages Wu, Jie; Yang, Xiaoqing; He, Zhi; Mao, Xianwen; Hatton, T. Alan; Jamison, Timothy F.; Angewandte Chemie - International Edition; vol. 53; nb. 32; (2014); p. 8416 - 8420; Angew. Chem.; vol. 126; nb. 32; (2014); p. 8556 - 8560,5 View in Reaxys

Mg O

Rx-ID: 38749076 View in Reaxys 47/344 Yield 79 %

Conditions & References Stage 1: With iodine, lithium chloride in tetrahydrofuran, Inert atmosphere, Cooling with ice Stage 2: in tetrahydrofuran, Time= 0.0166667h, T= 20 °C , p= 5171.62Torr , Flow reactor Stage 3: With [2,2]bipyridinyl, (-)-menthol in tetrahydrofuran, diethyl ether, Time= 0.166667h, T= 20 °C , Inert atmosphere, Flow reactor Wu, Jie; Yang, Xiaoqing; He, Zhi; Mao, Xianwen; Hatton, T. Alan; Jamison, Timothy F.; Angewandte Chemie - International Edition; vol. 53; nb. 32; (2014); p. 8416 - 8420; Angew. Chem.; vol. 126; nb. 32; (2014); p. 8556 - 8560,5 View in Reaxys

Rx-ID: 42916898 View in Reaxys 48/344 Yield 36 %

Conditions & References GeneralProcedure for Conjugate Reduction General procedure: A flask equipped a magnetic stirring bar was charged with α,α-unsaturatedketone 1 (1.0 mmol), tosylhydrazine(1.1 mmol), K2CO3 (1.5 mmol),and dioxane (2 ml). The reaction mixture was stirredunder a nitrogen atmosphere at 110

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°Cfor 24 h. The reaction mixture was cooled to room temperature; the reaction mixture was extracted with diethylether (5×3 ml). The combined extracts was washed withbrine and dried over MgSO4, and the crude product was adsorbed ontosilica gel and purified by column chromatography (silica gel, petroleum ether:ethyl acetate 20:1) gave the pure saturated carbonyl compound 4. With potassium carbonate, toluene-4-sulfonic acid hydrazide in 1,4-dioxane, Time= 24h, T= 110 °C , Inert atmosphere, chemoselective reaction Zhou, Xiaomeng; Li, Xiaokang; Zhang, Wei; Chen, Junmin; Tetrahedron Letters; vol. 55; nb. 37; (2014); p. 5137 - 5140 View in Reaxys

Rx-ID: 42916899 View in Reaxys 49/344 Yield

Conditions & References Reaction Steps: 2 1: sodium hydroxide / water; ethanol / 4 h / 0 - 20 °C 2: toluene-4-sulfonic acid hydrazide; potassium carbonate / 1,4-dioxane / 24 h / 110 °C / Inert atmosphere With potassium carbonate, toluene-4-sulfonic acid hydrazide, sodium hydroxide in 1,4-dioxane, ethanol, water Zhou, Xiaomeng; Li, Xiaokang; Zhang, Wei; Chen, Junmin; Tetrahedron Letters; vol. 55; nb. 37; (2014); p. 5137 - 5140 View in Reaxys

O O

Rx-ID: 281500 View in Reaxys 50/344 Yield

Conditions & References With ammonia, sodium, anschliessend Behandeln mit Butylbromid Kharasch; Sternfeld; Mayo; Journal of Organic Chemistry; vol. 5; (1940); p. 362,375 View in Reaxys Reaction Steps: 3 1: 1.) BuLi / 1.) THF, -78 deg C 2.) -100 deg C 2: 59 percent / tetrahydrofuran / -78 °C 3: 79 percent / conc. hydrochloric acid / CHCl3 / Heating With hydrogenchloride, n-butyllithium in tetrahydrofuran, chloroform Jones, Raymond C. F.; Nichols, John R.; Tetrahedron Letters; vol. 31; nb. 12; (1990); p. 1771 - 1774 View in Reaxys Reaction Steps: 3 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere 1.2: 4 h / -78 - 20 °C / Inert atmosphere 2.1: tetrahydrofuran; diethyl ether / -78 °C / Inert atmosphere 3.1: hydrogenchloride / water; chloroform / 4 h / Reflux With hydrogenchloride, n-butyllithium in tetrahydrofuran, diethyl ether, hexane, chloroform, water Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935

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View in Reaxys

Li Cl

Rx-ID: 2705300 View in Reaxys 51/344 Yield 62 %

Conditions & References With copper(l) iodide in diethyl ether, Time= 0.25h, T= -78 °C Baylis, Christopher J.; Odle, Stanley W.; Tyman, John H. P.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 132 - 141 View in Reaxys

98 %Chromat.

Partial alkylation of acid chlorides to corresponding ketones The following experimental procedure for the partial reduction of benzoyl chloride to 1-phenylpentanone is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.11 mL, 1.25 mmol) and 10 mL THF. After cooling to 0 °C, DIBALH (1.2 mL, 1.0 M in hexane, 1.2 mmol) was added dropwise and stirred for 3 h at same temperature. To the reaction mixture was slowly added benzoyl chloride (0.116 mL, 1.0 mmol) and stirred for 10 min. Then, n-BuLi (1.25 mL, 1.6 M in hexane, 2.0 mmol) was added and the mixture was stirred for 10 min again. The reaction was stopped by aqueous 1 N HCl (10 mL) and extracted with diethyl ether (2 × 10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded 1-phenylpentanone (159 mg, 98percent). All products in Table 3 were confirmed by comparison with NMR data reported in the literature.8 Stage 1: With morpholine, diisobutylaluminium hydride in tetrahydrofuran, hexane, Time= 0.166667h, T= 0 °C , Inert atmosphere Stage 2: in tetrahydrofuran, hexane, Time= 0.166667h, T= 0 °C Park, Jae Kyo; Shin, Won Kyu; An, Duk Keun; Tetrahedron Letters; vol. 54; nb. 24; (2013); p. 3199 - 3203 View in Reaxys

Cl Zn (v2)

Rx-ID: 2709296 View in Reaxys 52/344 Yield 85 %

Conditions & References With palladium, triphenylphosphine in tetrahydrofuran, Time= 3h, T= 50 °C , Inert atmosphere, Green chemistry, Negishi Coupling, Catalytic behavior Wu, Wei-Yi; Lin, Tze-Chiao; Takahashi, Tamotsu; Tsai, Fu-Yu; Mou, Chung-Yuan; ChemCatChem; vol. 5; nb. 4; (2013); p. 1011 - 1019 View in Reaxys

90 % Chromat.

With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, benzene, Time= 0.5h, T= 25 °C Negishi, Ei-ichi; Bagheri, Vahid; Chatterjee, Sugata; Luo, Fen-Tair; Miller, Joseph A.; Stoll, A. Timothy; Tetrahedron Letters; vol. 24; nb. 47; (1983); p. 5181 - 5184 View in Reaxys

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O O

(v2)

Rx-ID: 11243523 View in Reaxys 53/344 Yield

Conditions & References Stage 1: With copper(l) iodide in tetrahydrofuran, Time= 0.25h, T= -20 °C Stage 2: With N,N,N,N,-tetramethylethylenediamine in tetrahydrofuran, Time= 0.333333h, T= 20 °C , Further stages. Title compound not separated from byproducts. Erdik, Ender; Pekel, Oezgen Oemuer; Journal of Organometallic Chemistry; vol. 693; nb. 2; (2008); p. 338 - 342 View in Reaxys With copper(l) iodide in tetrahydrofuran, Time= 0.333333h, T= 25 °C , Inert atmosphere, Overall yield = 67 percentChromat. Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.; Journal of Organometallic Chemistry; vol. 745-746; (2013); p. 235 - 241 View in Reaxys With copper(l) iodide in tetrahydrofuran, Time= 0.333333h, T= 25 °C , Inert atmosphere, Overall yield = 78 percentChromat. Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.; Journal of Organometallic Chemistry; vol. 745-746; (2013); p. 235 - 241 View in Reaxys

Rx-ID: 21952611 View in Reaxys 54/344 Yield

Conditions & References Reaction Steps: 3 1: 67 percent / MnO2 / CH2Cl2 / 20 °C 2: 59 percent / tetrahydrofuran / -78 °C 3: 79 percent / conc. hydrochloric acid / CHCl3 / Heating With hydrogenchloride, manganese(IV) oxide in tetrahydrofuran, dichloromethane, chloroform Jones, Raymond C. F.; Nichols, John R.; Tetrahedron Letters; vol. 31; nb. 12; (1990); p. 1771 - 1774 View in Reaxys Reaction Steps: 3 1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C 2: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 3: tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere With manganese(IV) oxide in tetrahydrofuran, hexane, dichloromethane Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935 View in Reaxys Reaction Steps: 3 1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C 2: tetrahydrofuran; diethyl ether / -78 °C / Inert atmosphere 3: hydrogenchloride / water; chloroform / 4 h / Reflux

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With hydrogenchloride, manganese(IV) oxide in tetrahydrofuran, diethyl ether, dichloromethane, chloroform, water Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935 View in Reaxys

Rx-ID: 21952650 View in Reaxys 55/344 Yield

Conditions & References Reaction Steps: 2 1: 59 percent / tetrahydrofuran / -78 °C 2: 79 percent / conc. hydrochloric acid / CHCl3 / Heating With hydrogenchloride in tetrahydrofuran, chloroform Jones, Raymond C. F.; Nichols, John R.; Tetrahedron Letters; vol. 31; nb. 12; (1990); p. 1771 - 1774 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 2: tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere in tetrahydrofuran, hexane Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran; diethyl ether / -78 °C / Inert atmosphere 2: hydrogenchloride / water; chloroform / 4 h / Reflux With hydrogenchloride in tetrahydrofuran, diethyl ether, chloroform, water Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935 View in Reaxys

Rx-ID: 35202584 View in Reaxys 56/344 Yield 77 %

Conditions & References Stage 1: With (tetrahydrofuran)Zr(2,4,6-trimethylphenyl-NPiPr2)3CoN2, phenylsilane, lithium iodide in tetrahydrofuran, Time= 24h, T= 65 °C , Inert atmosphere, Glovebox Stage 2: With hydrogenchloride in tetrahydrofuran, water Zhou, Wen; Marquard, Seth L.; Bezpalko, Mark W.; Foxman, Bruce M.; Thomas, Christine M.; Organometallics; vol. 32; nb. 6; (2013); p. 1766 - 1772 View in Reaxys

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Rx-ID: 35749761 View in Reaxys 57/344 Yield

Conditions & References With (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, oxygen in hexane, Time= 4h, T= 150 °C , p= 15001.5Torr Sheng, Wen-Bing; Jiang, Qing; Luo, Wei-Ping; Guo, Can-Cheng; Journal of Organic Chemistry; vol. 78; nb. 11; (2013); p. 5691 - 5693 View in Reaxys

Rx-ID: 35749766 View in Reaxys 58/344 Yield 76 %

F F N

B–

K+

Rx-ID: 35881371 View in Reaxys 59/344 Yield 99 %

Conditions & References With [2,2]bipyridinyl, palladium(II) trifluoroacetate, water, trifluoroacetic acid in tetrahydrofuran, Time= 36h, T= 80 °C , Inert atmosphere, Schlenk technique Wang, Xingyong; Liu, Miaochang; Xu, Long; Wang, Qingzong; Chen, Jiuxi; Ding, Jinchang; Wu, Huayue; Journal of Organic Chemistry; vol. 78; nb. 11; (2013); p. 5273 - 5281 View in Reaxys

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HO O

N N

Rx-ID: 36051840 View in Reaxys 60/344 Yield 79 %

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

N O N+

I–

Rx-ID: 36051854 View in Reaxys 61/344 Yield

Conditions & References Reaction Steps: 4 1.1: 20 h / Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere 3.1: tetrahydrofuran; diethyl ether / -78 °C / Inert atmosphere 4.1: hydrogenchloride / water; chloroform / 4 h / Reflux With hydrogenchloride, n-butyllithium in tetrahydrofuran, diethyl ether, hexane, chloroform, water Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935 View in Reaxys

N O

N+

I–

Rx-ID: 36051858 View in Reaxys 62/344 Yield 30 %

Conditions & References in tetrahydrofuran, hexane, Time= 0.5h, T= -78 °C , Inert atmosphere Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935

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View in Reaxys

Rx-ID: 36051870 View in Reaxys 63/344 Yield

Conditions & References Reaction Steps: 4 1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 1.2: -78 °C / Inert atmosphere 2.1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C 3.1: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 4.1: tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere With manganese(IV) oxide, n-butyllithium in tetrahydrofuran, hexane, dichloromethane Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935 View in Reaxys Reaction Steps: 4 1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 1.2: -78 °C / Inert atmosphere 2.1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C 3.1: tetrahydrofuran; diethyl ether / -78 °C / Inert atmosphere 4.1: hydrogenchloride / water; chloroform / 4 h / Reflux With hydrogenchloride, manganese(IV) oxide, n-butyllithium in tetrahydrofuran, diethyl ether, hexane, dichloromethane, chloroform, water Jones, Raymond C. F.; Nichols, John R.; Organic and Biomolecular Chemistry; vol. 11; nb. 35; (2013); p. 5926 - 5935 View in Reaxys

O O

Zn (v2)

Rx-ID: 36343799 View in Reaxys 64/344 Yield

Conditions & References With copper(l) iodide in tetrahydrofuran, Time= 0.333333h, T= 25 °C , Inert atmosphere, Solvent, Overall yield = 91 percentChromat. Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.; Journal of Organometallic Chemistry; vol. 745-746; (2013); p. 235 - 241 View in Reaxys

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HO B N

Rx-ID: 36367733 View in Reaxys 65/344 Yield

Conditions & References

94 %

Alkyl Aryl Ketones 3 and 2-Arylbenzofurans 4; General Procedure General procedure: To a Schlenk tube with a magnetic stirring bar were charged the respective nitrile 1 (0.4 mmol), arylboronic acid 2 (0.8 mmol), Pd(OAc)2 (5 molpercent), bpy (10 molpercent), TFA (10 equiv), THF (2 mL), and H2O (0.4 mL) under N2 atmosphere. The reaction mixture was stirred at 80 °C for 36 h. After cooling to r.t., the mixture was poured into EtOAc (5 mL), which was washed with sat. aq NaHCO3 (2*10 mL) and then brine (1*10 mL). After extracting the aqueous layer with EtOAc (3*10 mL), the combined organic layers were dried (Na2SO4), and evaporated under vacuum. The residue was purified by flash column chromatography (hexane–EtOAc) to afford the desired products 3 or 4. All known compounds afforded analytical data identical to those reported literature previously (see Supporting Information for further details). With [2,2]bipyridinyl, palladium diacetate, trifluoroacetic acid in tetrahydrofuran, water, Time= 36h, T= 80 °C , Schlenk technique, Inert atmosphere Wang, Xingyong; Wang, Xiaodong; Liu, Miaochang; Ding, Jinchang; Chen, Jiuxi; Wu, Huayue; Synthesis (Germany); vol. 45; nb. 16; (2013); p. 2241 - 2244; Art.No: SS-2013-F0255-OP View in Reaxys

H HO

NH 2 O

Rx-ID: 36884585 View in Reaxys 66/344 Yield

Conditions & References With [(C6H6)(PCy3)(CO)RuH]+BF4 -, cyclopentene in toluene, Time= 12h, T= 120 °C , Inert atmosphere, Schlenk technique

80 %

Kalutharage, Nishantha; Yi, Chae S.; Angewandte Chemie - International Edition; vol. 52; nb. 51; (2013); p. 13651 - 13655; Angew. Chem.; vol. 125; nb. 51; (2013); p. 13896 - 13900 View in Reaxys

Rx-ID: 37329650 View in Reaxys 67/344 Yield

Conditions & References With [Ir(1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidine)(1,5-cyclooctadiene)Cl], deuterium in dichloromethane, T= -78 - 25 °C , regioselective reaction Cochrane, Alison R.; Irvine, Stephanie; Kerr, William J.; Reid, Marc; Andersson, Shalini; Nilsson, Goeran N.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 56; nb. 9-10; (2013); p. 451 - 454 View in Reaxys

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Rx-ID: 10398039 View in Reaxys 68/344 Yield

Conditions & References With potassium hydroxide, acetone, N,N'-bis[o-(diphenylphosphino)benzylidene]-(1S,2S)-diaiminocyclohexane, bis(1,5-cyclooctadiene)diiridium(I) dichloride in isopropyl alcohol, Time= 20h, T= 25 °C Li, Yan-Yun; Zhang, Xue-Qin; Dong, Zhen-Rong; Shen, Wei-Yi; Chen, Gui; Gao, Jing-Xing; Organic Letters; vol. 8; nb. 24; (2006); p. 5565 - 5567 View in Reaxys With bis(1,5-cyclooctadiene)diiridium(I) dichloride, bis(triphenylphosphine)iminium chloride, acetone, potassium hydoxide, N,N'-bis[o-(diphenylphosphino)benzylidene]-(1S,2S)-diaiminocyclohexane in dichloromethane, water, isopropyl alcohol, Time= 24h, T= 28 °C , Resolution of racemate, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Zhang, Juanni; Yang, Xiangren; Zhou, Han; Li, Yanyun; Dong, Zhenrong; Gao, Jingxing; Green Chemistry; vol. 14; nb. 5; (2012); p. 1289 - 1292 View in Reaxys

O O

I (v2)

Rx-ID: 33552965 View in Reaxys 69/344 Yield

Conditions & References With bis(acetylacetonate)nickel(II), bathophenanthroline, magnesium chloride, zinc in N,N-dimethyl acetamide, T= 25 °C , Inert atmosphere Wu, Fan; Lu, Wenbin; Qian, Qun; Ren, Qinghua; Gong, Hegui; Organic Letters; vol. 14; nb. 12; (2012); p. 3044 - 3047 View in Reaxys

O O

Rx-ID: 33695852 View in Reaxys 70/344 Yield 9 %Chromat., 91 %Chromat.

Conditions & References Time= 0.5h, T= 0 °C , Photolysis, Inert atmosphere Takahashi, Hiroki; Ito, Yoshikatsu; Structural Chemistry; vol. 23; nb. 2; (2012); p. 441 - 449 View in Reaxys

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Rx-ID: 33695853 View in Reaxys 71/344 Yield 15 %Chromat., 85 %Chromat.

Conditions & References Time= 0.5h, T= 0 °C , Photolysis, Inert atmosphere Takahashi, Hiroki; Ito, Yoshikatsu; Structural Chemistry; vol. 23; nb. 2; (2012); p. 441 - 449 View in Reaxys

N N N

Rx-ID: 33722905 View in Reaxys 72/344 Yield 76 %

Conditions & References Representative procedure: To a solution of 1-(azidomethyl)-4-methoxybenzene (8a) (81 mg, 0.5 mmol) in MeCN (0.5 mL) was added PhI(OAc) (1) (483.1 mg, 1.5 mmol) at 0 °C. The resultant suspension was stirred vigorously while a solution of tBuOOH (2) (5.0-6.0 M in decane, 360 μL, 2.0 mmol) was added dropwise over 1 h. After the addition, the reaction mixture was stirred for 11 h followed by chromatography on silica gel with n-hexanes/EtOAc (10:1) to yield 4-methoxybenzonitrile (9a) as a yellow oil (55.3 mg, 83percent). Stage 1: With tert.-butylhydroperoxide, [bis(acetoxy)iodo]benzene in decane, acetonitrile, T= 0 °C Stage 2: With water in decane, acetonitrile Zhao, Yi; Chew, Xinying; Leung, Gulice Y.C.; Yeung, Ying-Yeung; Tetrahedron Letters; vol. 53; nb. 35; (2012); p. 4766 4769 View in Reaxys

Li HO

Rx-ID: 3551422 View in Reaxys 73/344 Yield 96 %

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

85 %

in tetrahydrofuran, Time= 1h, T= -20 °C Bures, Edward; Nieman, James A.; Yu, Shuyuan; Spinazze, Patrick G.; Bontront, Jean-Louis J.; Hunt, Ian R.; Rauk, Arvi; Keay, Brian A.; Journal of Organic Chemistry; vol. 62; nb. 25; (1997); p. 8750 - 8759 View in Reaxys With lithium bromide in diethyl ether, T= 0 °C , Product distribution

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Perraud, Robert; Handel, Henri; Pierre, Jean-Louis; Bulletin de la Societe Chimique de France; vol. 2; nb. 5-6; (1980); p. 283 - 288 View in Reaxys With deuteromethanol, 1) THF, -20 deg C, 1 h, Yield given. Multistep reaction Yu, Shuyuan; Keay, Brian A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1991); p. 2600 - 2601 View in Reaxys

Rx-ID: 26019872 View in Reaxys 74/344 Yield

Conditions & References With diethylzinc in dichloromethane, Time= 2h, T= 20 °C , Title compound not separated from byproducts. Li, Lezhen; Cai, Peijie; Guo, Qingxiang; Xue, Song; Journal of Organic Chemistry; vol. 73; nb. 9; (2008); p. 3516 - 3522 View in Reaxys General Procedure for CF3CO2ZnEt -Mediated Rearrangement of Bromohydrins General procedure: A 25 mL round-bottom flask was charged with dry methylene chloride (2 mL), and diethylzinc (0.3ml, 0.3 mmol) was added via syringe under an atmosphere of nitrogen at 0°C. Then trifluoroacetic acid (22.5 μL, 0.3 mmol) was added dropwise via syringe under nitrogen and the resulting mixture was stirred for additional 30 mins. Bromohydrins (0.5 mmol) was added to the reaction mixture and then the ice bath was removed. The solution was allowed to stir at room temperature until TLC indicated complete consumption of the starting bromohydrins. The reaction mixture was concentrated in vacuo, and purified by column chromatograph packed with silica gel using petroleum ether/ethyl acetate (50:1 to 10:1) as eluent to afford the pure products. With t-C4H9OZnEt in dichloromethane, Time= 4h, T= 20 °C , Inert atmosphere Wang, Zhihui; Li, Meiyi; Zhang, Wenqin; Jia, Jiangnan; Wang, Fei; Xue, Song; Tetrahedron Letters; vol. 52; nb. 45; (2011); p. 5968 - 5971 View in Reaxys

O O

Rx-ID: 30068418 View in Reaxys 75/344 Yield 8 %Spectr.

Conditions & References With chlorodicarbonyl(1,2,3,4,5-pentaphenylcyclopentadienyl)ruthenium(II), potassium tert-butylate, sodium carbonate in tetrahydrofuran, toluene, Time= 24h, T= 60 °C , Resolution of racemate, Molecular sieve, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Engstroem, Karin; Vallin, Michaela; Syren, Per-Olof; Hult, Karl; Baeckvall, Jan-E.; Organic and Biomolecular Chemistry; vol. 9; nb. 1; (2011); p. 81 - 82 View in Reaxys

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Rx-ID: 2937002 View in Reaxys 76/344 Yield 98 %

Conditions & References Stage 1: With iron(III) chloride in hexanes, Time= 3h, T= -78 °C , Inert atmosphere Stage 2: in hexanes, Time= 15h, T= -78 - 25 °C , Inert atmosphere Stage 3: With hydrogenchloride, water in hexanes Eisch, John J.; Sohn, Jane U.; Rabinowitz, Edon J.; European Journal of Organic Chemistry; nb. 15; (2010); p. 2971 - 2977 View in Reaxys

75 %

in diethyl ether, Time= 3h, T= 20 °C Cook, Lawrence S.; Wakefield, Basil J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 2392 - 2397 View in Reaxys

62 %

in diethyl ether, Time= 3h, Ambient temperature Beak, Peter; Pfeifer, Lance A.; Journal of Physical Organic Chemistry; vol. 10; nb. 7; (1997); p. 537 - 541 View in Reaxys

Rx-ID: 29565196 View in Reaxys 77/344 Yield 100 %

Conditions & References With oxygen, vanadium(V) oxychloride in ethyl acetate, 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: 29565197 View in Reaxys 78/344 Yield 91 %

Conditions & References With oxygen, vanadium(V) oxychloride 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

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(v2)

(v5)

Rx-ID: 29741438 View in Reaxys 79/344 Yield

Conditions & References

96 %

With bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran, T= 20 °C , Inert atmosphere Pena-Lopez, Miguel; Ayan-Varela, Miguel; Sarandeses, Luis A.; Perez Sestelo, Jose; Chemistry - A European Journal; vol. 16; nb. 32; (2010); p. 9905 - 9909 View in Reaxys

Br Mg

Rx-ID: 657788 View in Reaxys 80/344 Yield

Conditions & References

89 %

Stage 1: in 2-methyltetrahydrofuran, Time= 4h, Inert atmosphere, Reflux, Grignard reaction Stage 2: With water, ammonium chloride in 2-methyltetrahydrofuran, Inert atmosphere, chemoselective reaction Zhong, Weihui; Wu, Yaotiao; Zhang, Xingxian; Journal of Chemical Research; nb. 6; (2009); p. 370 - 373 View in Reaxys With diethyl ether, anschliessend Behandeln mit verd. wss. Schwefelsaeure Evans; Journal of the Chemical Society; (1936); p. 785,788 View in Reaxys OH

Rx-ID: 29032175 View in Reaxys 81/344 Yield

Conditions & References

22 %Spectr. With chloro(1,5-cyclooctadiene)rhodium(I) dimer, potassium tert-butylate, triphenylphosphine in tetrahydrofuran, Time= 18h, T= 40 °C , optical yield given as percent de Ahlsten, Nanna; Martin-Matute, Belen; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2657 - 2666 View in Reaxys

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V–

Li+ (v4)

Rx-ID: 28314543 View in Reaxys 82/344 Yield

Conditions & References

45 %, 55 %

Stage 1: in tetrahydrofuran, Time= 12h, T= 25 °C , Inert atmosphere Stage 2: With water, Acidic conditions Eisch, John J.; Fregene, Paul O.; European Journal of Organic Chemistry; nb. 26; (2008); p. 4482 - 4492 View in Reaxys

O N

Rx-ID: 11077978 View in Reaxys 83/344 Yield

Conditions & References

40 %, 30 %

Stage 1: With sodium methylate in methanol, T= 20 °C Stage 2: With sulfuric acid in methanol, T= 90 °C , Further stages. Simoneau, Christopher A.; Strohl, Alexis M.; Ganem, Bruce; Tetrahedron Letters; vol. 48; nb. 10; (2007); p. 1809 - 1811 View in Reaxys

OH H

Li O

Rx-ID: 2677851 View in Reaxys 84/344 Yield

Conditions & References

12 %, 68 %

Stage 1: in tetrahydrofuran, Time= 0.333333h, T= -78 °C Stage 2: With N-(tert-butyl)benzenesulfinimidoyl chloride in tetrahydrofuran, Time= 5h, T= -78 °C Crawford, James J.; Henderson, Kenneth W.; Kerr, William J.; Organic Letters; vol. 8; nb. 22; (2006); p. 5073 - 5076 View in Reaxys With vanadium(III) chloride in dichloromethane, Time= 16h, Heating, var. solvent, temp., time, Product distribution Hirao, Toshikazu; Misu, Daisuke; Agawa, Toshio; Journal of the American Chemical Society; vol. 107; nb. 24; (1985); p. 7179 - 7181 View in Reaxys O

SiH

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O Si

Rx-ID: 10105371 View in Reaxys 85/344 Yield

Conditions & References

59 %

With 1-methyl-pyrrolidin-2-one, platinum(IV) oxide, sodium acetate, Time= 1h, T= 70 °C Hamze, Abdallah; Provot, Olivier; Alami, Mouad; Brion, Jean-Daniel; Organic Letters; vol. 8; nb. 5; (2006); p. 931 - 934 View in Reaxys

(v2)

Mn Cl

Rx-ID: 10214243 View in Reaxys 86/344 Yield 94 %

Conditions & References With chloro-trimethyl-silane, [copper(I)(acetonitrile)2(PPh3)2](BF4) in tetrahydrofuran, T= 0 °C Deshmukh; Jadhav, Sunil; Anbhule; Mali; Suryawanshi; Journal of Chemical Research; nb. 4; (2006); p. 248 - 250 View in Reaxys

Li O

Rx-ID: 10417321 View in Reaxys 87/344 Yield 88 %

Conditions & References Stage 1: in tetrahydrofuran, hexane, Time= 0.341667h, T= -78 °C Stage 2: With N-(tert-butyl)benzenesulfinimidoyl chloride in tetrahydrofuran, Time= 5h, T= -78 - 20 °C Crawford, James J.; Henderson, Kenneth W.; Kerr, William J.; Organic Letters; vol. 8; nb. 22; (2006); p. 5073 - 5076 View in Reaxys

OH H

Rx-ID: 9779249 View in Reaxys 88/344

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Yield

Conditions & References

10 % Chromat., 60 % Chromat.

With sodium hypochlorite, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, T= 20 °C , pH= 8.5 - 9 Bright, Zack R.; Luyeye, Cedric R.; Morton, Angela Ste. Marie; Sedenko, Marina; Landolt, Robert G.; Bronzi, Matthew J.; Bohovic, Katherine M.; Gonser, M. W. Alex; Lapainis, Theodore E.; Hendrickson, William H.; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 684 - 687 View in Reaxys

NH 2

NH O

Rx-ID: 9867290 View in Reaxys 89/344 Yield

Conditions & References in tetrahydrofuran, hexane, Time= 1h, T= -78 °C Di Nunno, Leonardo; Scilimati, Antonio; Vitale, Paola; Tetrahedron; vol. 61; nb. 10; (2005); p. 2623 - 2630 View in Reaxys in tetrahydrofuran, hexane, Time= 8h, T= -78 °C Di Nunno, Leonardo; Scilimati, Antonio; Vitale, Paola; Tetrahedron; vol. 61; nb. 10; (2005); p. 2623 - 2630 View in Reaxys

O O N

Br–

P+

Rx-ID: 9876095 View in Reaxys 90/344 Yield 83 %

Conditions & References Stage 1: With n-butyllithium in tetrahydrofuran, hexane, T= -15 °C Stage 2: in tetrahydrofuran, hexane, T= -78 - 20 °C , Wittig reaction Stage 3: With hydrogenchloride in tetrahydrofuran, diethyl ether, hexane, T= 20 °C Murphy, John A.; Commeureuc, Aurelien G. J.; Snaddon, Thomas N.; McGuire, Thomas M.; Khan, Tanweer A.; Hisler, Kevin; Dewis, Mark L.; Carling, Robert; Organic Letters; vol. 7; nb. 7; (2005); p. 1427 - 1429 View in Reaxys

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Rx-ID: 10199322 View in Reaxys 91/344 Yield

Conditions & References With (CO)4(palladium)4(acetate)4, Time= 2h, T= 60 °C , Title compound not separated from byproducts Stolarov; Dobrokhotova; Kryukova; Kozitsyna; Gekhman; Vargaftik; Moiseev; Russian Chemical Bulletin; vol. 54; nb. 3; (2005); p. 803 - 806 View in Reaxys

n-BuCOCr(CO)5(1-)NMe4 (1+)

O H

Rx-ID: 10240813 View in Reaxys 92/344 Yield

Conditions & References

78 %, 8 %

With tris-(o-tolyl)phosphine, palladium diacetate in hexane, Time= 24h, T= 20 °C Yamane, Motoki; Kubota, Yuko; Narasaka, Koichi; Bulletin of the Chemical Society of Japan; vol. 78; nb. 2; (2005); p. 331 340 View in Reaxys

38 %, 20 %

With palladium diacetate, tris-(o-tolyl)phosphine in toluene, Time= 24h, T= 20 °C Yamane, Motoki; Kubota, Yuko; Narasaka, Koichi; Bulletin of the Chemical Society of Japan; vol. 78; nb. 2; (2005); p. 331 340 View in Reaxys O

O O

Rx-ID: 10394130 View in Reaxys 93/344

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Yield 41 % Chromat.

Conditions & References With aluminum oxide, T= 449.85 °C , Title compound not separated from byproducts Glinski; Koscik; Jerzak; Synoradzki; Polish Journal of Chemistry; vol. 79; nb. 6; (2005); p. 995 - 1001 View in Reaxys

6-t-butyl-12-p-tolyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azastibocine

Rx-ID: 13138355 View in Reaxys 94/344 Yield

Conditions & References Reaction Steps: 2 1.1: 35 percent / tetrahydrofuran / -78 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -15 °C 2.2: tetrahydrofuran; hexane / -78 - 20 °C 2.3: 83 percent / aq. HCl / tetrahydrofuran; hexane; diethyl ether / 20 °C With n-butyllithium in tetrahydrofuran, hexane, 2.2: Wittig reaction Murphy, John A.; Commeureuc, Aurelien G. J.; Snaddon, Thomas N.; McGuire, Thomas M.; Khan, Tanweer A.; Hisler, Kevin; Dewis, Mark L.; Carling, Robert; Organic Letters; vol. 7; nb. 7; (2005); p. 1427 - 1429 View in Reaxys Reaction Steps: 2 1: 92 percent / pyridine; CH2Cl2 / 1 h / 0 - 20 °C 2: 91 percent / tetrahydrofuran / 1 h / 0 °C in tetrahydrofuran, pyridine, dichloromethane Labeeuw, Olivier; Phansavath, Phannarath; Genet, Jean-Pierre; Tetrahedron Letters; vol. 45; nb. 38; (2004); p. 7107 - 7110 View in Reaxys

Rx-ID: 9246860 View in Reaxys 95/344 Yield 97 %

Conditions & References With cerium(III) sulfate, barium bromate in water, acetonitrile, Time= 6h, Heating Shaabani, Ahmad; Lee, Donald G.; Synthetic Communications; vol. 33; nb. 11; (2003); p. 1845 - 1854 View in Reaxys

85 %

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

55 % Chromat.

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

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O Si

Si Si O

N N

Rx-ID: 9641808 View in Reaxys 96/344 Yield

Conditions & References

22 %, 32 %, Stage 1: With N,N,N,N,-tetramethylethylenediamine in tetrahydrofuran, T= -78 - 0 °C 14 %, 14 % Stage 2: in tetrahydrofuran, Time= 0.25h, T= -78 °C , Further stages. Jozwiak, Andrzej; Brzezinski, Jacek Z.; Plotka, Mieczyslaw W.; Szczesniak, Aleksandra K.; Malinowski, Zbigniew; Epsztajn, Jan; European Journal of Organic Chemistry; nb. 15; (2004); p. 3254 - 3261 View in Reaxys

O Si

Si O

O N

Rx-ID: 9641818 View in Reaxys 97/344 Yield 49 %, 7 %, 16 %

Conditions & References Stage 1: With N,N,N,N,-tetramethylethylenediamine in tetrahydrofuran, T= -78 - 0 °C Stage 2: in tetrahydrofuran, Time= 0.25h, T= -78 °C , Further stages. Jozwiak, Andrzej; Brzezinski, Jacek Z.; Plotka, Mieczyslaw W.; Szczesniak, Aleksandra K.; Malinowski, Zbigniew; Epsztajn, Jan; European Journal of Organic Chemistry; nb. 15; (2004); p. 3254 - 3261 View in Reaxys

41/127

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O O N

Rx-ID: 9715673 View in Reaxys 98/344 Yield 91 %

Conditions & References in tetrahydrofuran, Time= 1h, T= 0 °C Labeeuw, Olivier; Phansavath, Phannarath; Genet, Jean-Pierre; Tetrahedron Letters; vol. 45; nb. 38; (2004); p. 7107 - 7110 View in Reaxys

Br O

Rx-ID: 5102235 View in Reaxys 99/344 Yield 91 %

Conditions & References Multistep reaction Bertini, Vincenzo; Pocci, Marco; Lucchesini, Francesco; Alfei, Silvana; De Munno, Angela; Synlett; nb. 6; (2003); p. 864 866 View in Reaxys 1,3-dithiane polymer supported synthesis, Yield given, Multistep reaction Bertini, Vincenzo; Lucchesini, Francesco; Pocci, Marco; De Munno, Angela; Tetrahedron Letters; vol. 39; nb. 50; (1998); p. 9263 - 9266 View in Reaxys

Rx-ID: 9300203 View in Reaxys 100/344 Yield 87 %

Conditions & References Stage 1: With indium(III) chloride in tetrahydrofuran, hexane, Time= 0.5h, T= -78 °C Stage 2: With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, hexane, Time= 3h, T= 66 °C , p= 760Torr Lee, Phil Ho; Lee, Sung Wook; Lee, Kooyeon; Organic Letters; vol. 5; nb. 7; (2003); p. 1103 - 1106 View in Reaxys

42/127

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S N+

F O–

Rx-ID: 9300242 View in Reaxys 101/344 Yield 72 %

Conditions & References in diethyl ether, Time= 3h, T= -78 - 20 °C Mutoh, Yuichiro; Murai, Toshiaki; Organic Letters; vol. 5; nb. 8; (2003); p. 1361 - 1364 View in Reaxys

O Se

S N+

F F

O–

Rx-ID: 9300243 View in Reaxys 102/344 Yield 26 %, 70 %

Conditions & References in diethyl ether, Time= 3h, T= -78 - 20 °C Mutoh, Yuichiro; Murai, Toshiaki; Organic Letters; vol. 5; nb. 8; (2003); p. 1361 - 1364 View in Reaxys

Mg O

Rx-ID: 9329060 View in Reaxys 103/344 Yield 51 % Chromat., 26 % Chromat.

Conditions & References With Tridecane, dichlorobis(trimethylphosphine)nickel in tetrahydrofuran, T= 60 °C Miller, Joseph A.; Dankwardt, John W.; Tetrahedron Letters; vol. 44; nb. 9; (2003); p. 1907 - 1910 View in Reaxys

S Mg N

Rx-ID: 9329065 View in Reaxys 104/344 Yield 53 % Chromat., 7 % Chromat.

43/127

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View in Reaxys

Na +

Zn (v2)

O–

Rx-ID: 9509339 View in Reaxys 105/344 Yield

Conditions & References

85 %

Stage 1: With chloroformic acid ethyl ester in tetrahydrofuran, Time= 0.25h, T= 20 °C Stage 2: With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, Time= 14h, T= 70 °C , Negishi-type cross-coupling Wang, Donghui; Zhang, Zhaoguo; Organic Letters; vol. 5; nb. 24; (2003); p. 4645 - 4648 View in Reaxys

I (v2)

Rx-ID: 9536661 View in Reaxys 106/344 Yield

Conditions & References With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, Heating, Negishi-type cross-coupling

86 %

Wang, Donghui; Zhang, Zhaoguo; Organic Letters; vol. 5; nb. 24; (2003); p. 4645 - 4648 View in Reaxys

Rx-ID: 9588964 View in Reaxys 107/344 Yield

Conditions & References

81 %

With dihydrogen peroxide, vanadia, Aliquat 336 in water, Time= 12h, Heating Li, Chunbao; Zheng, Pengwu; Li, Jie; Zhang, Hang; Cui, Yi; Shao, Qiyun; Ji, Xiujie; Zhang, Jian; Zhao, Pengying; Xu, Yanli; Angewandte Chemie - International Edition; vol. 42; nb. 41; (2003); p. 5063 - 5066 View in Reaxys

Rx-ID: 14300517 View in Reaxys 108/344

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Yield

Conditions & References Reaction Steps: 2 1: 95 percent / diethyl ether / 0.01 h / 20 °C 2: 26 percent / diethyl ether / 3 h / -78 - 20 °C in diethyl ether Mutoh, Yuichiro; Murai, Toshiaki; Organic Letters; vol. 5; nb. 8; (2003); p. 1361 - 1364 View in Reaxys

O Li

Rx-ID: 9125493 View in Reaxys 109/344 Yield

Conditions & References Stage 1: in tetrahydrofuran, Time= 1h, T= 0 °C Stage 2: With acetic acid in tetrahydrofuran, water, T= 0 °C , Further stages. Jackson, Mary M.; Leverett, Carolyn; Toczko, Jennifer F.; Roberts, John C.; Journal of Organic Chemistry; vol. 67; nb. 14; (2002); p. 5032 - 5035 View in Reaxys

O S

Rx-ID: 9183505 View in Reaxys 110/344 Yield 79 %

Conditions & References With o-iodoxybenzoic acid monohydrate in dimethyl sulfoxide, Time= 9h, T= 25 °C Wu, Yikang; Shen, Xin; Huang, Jia-Hui; Tang, Chao-Jun; Liu, He-Hua; Hu, Qi; Tetrahedron Letters; vol. 43; nb. 36; (2002); p. 6443 - 6445 View in Reaxys

Li2Ti(OiPr)4 O

Rx-ID: 9234989 View in Reaxys 111/344 Yield

Conditions & References

7 % Spectr., in tetrahydrofuran, Time= 24h, T= 25 °C 92 % Eisch, John J.; Gitua, John N.; European Journal of Inorganic Chemistry; nb. 12; (2002); p. 3091 - 3096 Spectr. View in Reaxys

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Rx-ID: 2068044 View in Reaxys 112/344 Yield

Conditions & References

90 %

With tri-n-butyl-tin hydride, indium(III) chloride in tetrahydrofuran, Time= 5h, T= 20 °C Inoue, Katsuyuki; Sawada, Akemi; Shibata, Ikuya; Baba, Akio; Tetrahedron Letters; vol. 42; nb. 28; (2001); p. 4661 - 4663 View in Reaxys in N,N,N,N,N,N-hexamethylphosphoric triamide, Ambient temperature, Irradiation, transient absorption spectra at various times after irradiation; other solvents, Rate constant, Mechanism Kimura, Norio; Takamuku, Setsuo; Bulletin of the Chemical Society of Japan; vol. 64; nb. 8; (1991); p. 2433 - 2437 View in Reaxys

Rx-ID: 2117026 View in Reaxys 113/344 Yield

Conditions & References

80 %

With gallium hydrogen dichloride, triethyl borane in tetrahydrofuran, Time= 9h, T= 0 °C Mikami, Satoshi; Fujita, Kazuya; Nakamura, Tomoaki; Yorimitsu, Hideki; Shinokubo, Hiroshi; Matsubara, Seijiro; Oshima, Koichiro; Organic Letters; vol. 3; nb. 12; (2001); p. 1853 - 1855 View in Reaxys in N,N,N,N,N,N-hexamethylphosphoric triamide, Ambient temperature, Irradiation, transient absorption spectra at various times after irradiation; other solvents, Rate constant, Mechanism Kimura, Norio; Takamuku, Setsuo; Bulletin of the Chemical Society of Japan; vol. 64; nb. 8; (1991); p. 2433 - 2437 View in Reaxys

Rx-ID: 8764543 View in Reaxys 114/344 Yield 20 % Chromat., 68 % Chromat.,

Conditions & References in tetrahydrofuran, Time= 24h, T= 20 °C , Product distribution, Further Variations: reaction times Nudelman; Garcia; Journal of Organic Chemistry; vol. 66; nb. 4; (2001); p. 1387 - 1394 View in Reaxys

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12 % Chromat.

Rx-ID: 8806680 View in Reaxys 115/344 Yield 88 %

Conditions & References With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 1.5h, T= 20 °C Ooi; Ooi, Takashi; Sugimoto; Sugimoto, Hayato; Maruoka; Maruoka, Keiji; Heterocycles; vol. 54; nb. 2; (2001); p. 593 596 View in Reaxys

O Si O I

Rx-ID: 8806685 View in Reaxys 116/344 Yield 91 %

O Si O I

Rx-ID: 8806687 View in Reaxys 117/344 Yield 80 %

47/127

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O Si O I

Rx-ID: 8806688 View in Reaxys 118/344 Yield 86 %

O Si I

Rx-ID: 8806699 View in Reaxys 119/344 Yield 96 %

O Si

Rx-ID: 8806705 View in Reaxys 120/344 Yield 77 %

Rx-ID: 8826416 View in Reaxys 121/344

48/127

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Yield

Conditions & References With titanium(II) diisopropoxide in tetrahydrofuran, Time= 12h, T= 25 °C Eisch, John J.; Gitua, John N.; Otieno, Peter O.; Shi, Xian; Journal of Organometallic Chemistry; vol. 624; nb. 1-2; (2001); p. 229 - 238 View in Reaxys

Rx-ID: 8567086 View in Reaxys 122/344 Yield

Conditions & References With potassium acetate, tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, Time= 3h, T= 65 °C , Substitution

75 %

Kabalka, George W.; Malladi, Rama R.; Tejedor, David; Kelley, Shane; Tetrahedron Letters; vol. 41; nb. 7; (2000); p. 999 1001 View in Reaxys

Li O

Rx-ID: 36626702 View in Reaxys 123/344 Yield 79 %

Conditions & References in tetrahydrofuran, methanol, hexane, Time= 24h, T= -78 - 0 °C , Inert atmosphere Orita, Akihiro; Yasui, Yutaka; Otera, Junzo; Organic Process Research and Development; vol. 4; nb. 5; (2000); p. 337 - 341 View in Reaxys

Rx-ID: 5210181 View in Reaxys 124/344 Yield 40 %

Conditions & References With caesium carbonate, tetrakis(triphenylphosphine) palladium(0) in toluene, T= 100 °C Haddach, Mustapha; McCarthy, James R.; Tetrahedron Letters; vol. 40; nb. 16; (1999); p. 3109 - 3112 View in Reaxys

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Rx-ID: 5220678 View in Reaxys 125/344 Yield

Conditions & References With Coprinus peroxidase (CiP), 2-methoxy-phenol in water, Time= 20h, T= 408 °C , phosphate buffer pH 7.0; enzyme-catalyzed kinetic resolution of chiral hydroperoxides in the presence and absence of guaiacol; selectivity; enantiomeric excess; CiPcatalyzed disproportionation; radical formation; mechanism; CiP-catalyzed sulfoxidation, Product distribution Adam, Waldemar; Mock-Knoblauch, Cordula; Saha-Moeller, Chantu R.; Journal of Organic Chemistry; vol. 64; nb. 13; (1999); p. 4834 - 4839 View in Reaxys

Br Sn

Rx-ID: 4830818 View in Reaxys 126/344 Yield 35 %

Conditions & References With tetrabutylammomium bromide in toluene, Time= 4h, T= 80 °C Yasuda, Makoto; Hayashi, Keiko; Katoh, Yasuhiro; Shibata, Ikuya; Baba, Akio; Journal of the American Chemical Society; vol. 120; nb. 4; (1998); p. 715 - 721 View in Reaxys

Rx-ID: 4830830 View in Reaxys 127/344 Yield 33 %

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Cl Br–

Mn (v2)

N+

Rx-ID: 4870562 View in Reaxys 128/344 Yield

Conditions & References

85 %

in tetrahydrofuran, Time= 2h, T= 20 °C Cahiez, Gerard; Razafintsalama, Lynah; Laboue, Blandine; Chau, Francois; Tetrahedron Letters; vol. 39; nb. 8; (1998); p. 849 - 852 View in Reaxys

N+

Cl (v2)

Mn O

Cl –

Rx-ID: 4870565 View in Reaxys 129/344 Yield

Conditions & References

85 %

in tetrahydrofuran, Time= 2h, T= 20 °C Cahiez, Gerard; Razafintsalama, Lynah; Laboue, Blandine; Chau, Francois; Tetrahedron Letters; vol. 39; nb. 8; (1998); p. 849 - 852 View in Reaxys

H O

O H

Rx-ID: 4915509 View in Reaxys 130/344 Yield

Conditions & References With n-butyllithium in Petroleum ether, Time= 30h, Product distribution, Mechanism Wiberg, Kenneth B.; Snoonian, John R.; Journal of Organic Chemistry; vol. 63; nb. 5; (1998); p. 1390 - 1401 View in Reaxys

Rx-ID: 5023159 View in Reaxys 131/344

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Yield

Conditions & References With water, silica gel, Yield given Ortiz-Marciales, Margarita; Tirado, Liz M.; Colon, Roberto; Ufret, Maria L.; Figueroa, Ruth; Lebron, Marisabel; DeJesus, Melvin; Martinez, Johanna; Malave, Tania; Synthetic Communications; vol. 28; nb. 21; (1998); p. 4067 - 4075 View in Reaxys

4-isopropyl-phenyl magnesium halide O

Rx-ID: 16709224 View in Reaxys 132/344 Yield

Conditions & References Reaction Steps: 2 1: 1) hexane, -78 deg C, 1 h; -78 deg C -> 25 deg C, 2) hexane, THF, -10 deg C 2: H2O, silica gel With water, silica gel Ortiz-Marciales, Margarita; Tirado, Liz M.; Colon, Roberto; Ufret, Maria L.; Figueroa, Ruth; Lebron, Marisabel; DeJesus, Melvin; Martinez, Johanna; Malave, Tania; Synthetic Communications; vol. 28; nb. 21; (1998); p. 4067 - 4075 View in Reaxys Reaction Steps: 2 1: CuBr / tetrahydrofuran / -78 - 0 °C 2: H2O, silica gel With water, silica gel, copper(I) bromide in tetrahydrofuran Ortiz-Marciales, Margarita; Tirado, Liz M.; Colon, Roberto; Ufret, Maria L.; Figueroa, Ruth; Lebron, Marisabel; DeJesus, Melvin; Martinez, Johanna; Malave, Tania; Synthetic Communications; vol. 28; nb. 21; (1998); p. 4067 - 4075 View in Reaxys

O HO

Li HO

Rx-ID: 3551423 View in Reaxys 133/344 Yield

Conditions & References in tetrahydrofuran, T= 67 °C , variation of condition; other carboxylic acids, Product distribution, Mechanism Einhorn; Luche; Tetrahedron Letters; vol. 32; nb. 24; (1991); p. 2771 - 2774 View in Reaxys With lithium bromide in diethyl ether, Ambient temperature, Product distribution Perraud, Robert; Handel, Henri; Pierre, Jean-Louis; Bulletin de la Societe Chimique de France; vol. 2; nb. 5-6; (1980); p. 283 - 288 View in Reaxys in tetrahydrofuran, Time= 0.5h, T= -78 °C , Mechanism Beak, Peter; Pfeifer, Lance A.; Journal of Physical Organic Chemistry; vol. 10; nb. 7; (1997); p. 537 - 541 View in Reaxys

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in tetrahydrofuran, Time= 0.5h, T= -78 °C , Title compound not separated from byproducts Beak, Peter; Pfeifer, Lance A.; Journal of Physical Organic Chemistry; vol. 10; nb. 7; (1997); p. 537 - 541 View in Reaxys

O O

Rx-ID: 4675563 View in Reaxys 134/344 Yield 68 %

Conditions & References T= 650 °C , p= 0.01Torr Aitken, R. Alan; Thomas, Andrew W.; Synlett; vol. 1997; nb. 3; (1997); p. 293 - 294 View in Reaxys

O O

Rx-ID: 4720291 View in Reaxys 135/344 Yield 10 % Spectr., 20 % Spectr.

Conditions & References in benzene-d6, Time= 1h, Ambient temperature, Irradiation, Title compound not separated from byproducts Diederichsen, Ulf; Curran, Dennis P.; Journal of Organometallic Chemistry; vol. 531; nb. 1-2; (1997); p. 9 - 12 View in Reaxys

Ge I

Rx-ID: 4720292 View in Reaxys 136/344 Yield 7 % Spectr.

Conditions & References in benzene-d6, Time= 1h, Ambient temperature, Irradiation Diederichsen, Ulf; Curran, Dennis P.; Journal of Organometallic Chemistry; vol. 531; nb. 1-2; (1997); p. 9 - 12 View in Reaxys

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Li 2H

Rx-ID: 4760971 View in Reaxys 137/344 Yield

Conditions & References in tetrahydrofuran, T= -78 °C , Title compound not separated from byproducts Beak, Peter; Pfeifer, Lance A.; Journal of Physical Organic Chemistry; vol. 10; nb. 7; (1997); p. 537 - 541 View in Reaxys

O–

Li+

Li O

Rx-ID: 4760974 View in Reaxys 138/344 Yield

Conditions & References in tetrahydrofuran, Time= 0.00833333h, T= -78 °C , Title compound not separated from byproducts Beak, Peter; Pfeifer, Lance A.; Journal of Physical Organic Chemistry; vol. 10; nb. 7; (1997); p. 537 - 541 View in Reaxys

O S

Rx-ID: 4841265 View in Reaxys 139/344 Yield

Conditions & References With Ra-Ni, pyridinium chlorochromate, 1.) EtOH, 70 deg C, 4 h, rt, 20 h, 2.) CH2Cl2, Yield given. Multistep reaction. Yields of byproduct given Pohmakotr, Manat; Thisayukta, Jirakorn; Tetrahedron Letters; vol. 38; nb. 38; (1997); p. 6759 - 6762 View in Reaxys

O S

54/127

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Rx-ID: 4841266 View in Reaxys 140/344 Yield

Conditions & References With Ra-Ni in ethanol, 70 deg C, 4 h, rt, 20 h Pohmakotr, Manat; Thisayukta, Jirakorn; Tetrahedron Letters; vol. 38; nb. 38; (1997); p. 6759 - 6762 View in Reaxys

I O

Rx-ID: 4982380 View in Reaxys 141/344 Yield

Conditions & References With bis(acetylacetonate)nickel(II) in tetrahydrofuran, T= 0 °C , other solvent, other educt, Product distribution Ichiyanagi, Tsuyoshi; Kuniyama, Satoru; Shimizu, Makoto; Fujisawa, Tamotsu; Chemistry Letters; nb. 11; (1997); p. 1149 - 1150 View in Reaxys

I O

Rx-ID: 4982381 View in Reaxys 142/344 Yield

Conditions & References

37 %, 10 %

With bis(acetylacetonate)nickel(II) in tetrahydrofuran, T= 0 °C Ichiyanagi, Tsuyoshi; Kuniyama, Satoru; Shimizu, Makoto; Fujisawa, Tamotsu; Chemistry Letters; nb. 11; (1997); p. 1149 - 1150 View in Reaxys

Rx-ID: 4990255 View in Reaxys 143/344 Yield 37 %, 10 %

Conditions & References With bis(acetylacetonate)nickel(II), methyl magnesium iodide in tetrahydrofuran, T= 0 °C

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Ichiyanagi, Tsuyoshi; Kuniyama, Satoru; Shimizu, Makoto; Fujisawa, Tamotsu; Chemistry Letters; nb. 11; (1997); p. 1149 - 1150 View in Reaxys

Rx-ID: 17069902 View in Reaxys 144/344 Yield

Conditions & References Reaction Steps: 2 1: 73 percent / ZnBr2 / CH2Cl2 / 48 h / Ambient temperature 2: 1.) Ra-Ni, 2.) PCC / 1.) EtOH, 70 deg C, 4 h, rt, 20 h, 2.) CH2Cl2 With Ra-Ni, pyridinium chlorochromate, zinc dibromide in dichloromethane Pohmakotr, Manat; Thisayukta, Jirakorn; Tetrahedron Letters; vol. 38; nb. 38; (1997); p. 6759 - 6762 View in Reaxys Reaction Steps: 2 1: 73 percent / ZnBr2 / CH2Cl2 / 48 h / Ambient temperature 2: Ra-Ni / ethanol / 70 deg C, 4 h, rt, 20 h With Ra-Ni, zinc dibromide in ethanol, dichloromethane Pohmakotr, Manat; Thisayukta, Jirakorn; Tetrahedron Letters; vol. 38; nb. 38; (1997); p. 6759 - 6762 View in Reaxys

Rx-ID: 17159803 View in Reaxys 145/344 Yield

Conditions & References Reaction Steps: 3 1: tert-butyllithium / diethyl ether / 0.75 h / -78 °C 2: PhCO2D, PhCO2H / tetrahydrofuran / 0.5 h / -78 °C 3: tetrahydrofuran / 0.01 h / -78 °C With benzoic-acid-d1, tert.-butyl lithium, benzoic acid in tetrahydrofuran, diethyl ether Beak, Peter; Pfeifer, Lance A.; Journal of Physical Organic Chemistry; vol. 10; nb. 7; (1997); p. 537 - 541 View in Reaxys

Rx-ID: 17163554 View in Reaxys 146/344

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Yield

Conditions & References Reaction Steps: 2 1: PhCO2D, PhCO2H / tetrahydrofuran / 0.5 h / -78 °C 2: tetrahydrofuran / 0.01 h / -78 °C With benzoic-acid-d1, benzoic acid in tetrahydrofuran Beak, Peter; Pfeifer, Lance A.; Journal of Physical Organic Chemistry; vol. 10; nb. 7; (1997); p. 537 - 541 View in Reaxys

OH O

copper oxide-chromium oxide catalyst O

Rx-ID: 17411621 View in Reaxys 147/344 Yield

Conditions & References Reaction Steps: 2 1: 87 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 15 min; 2.) warm up to RT, 1 h 2: 68 percent / 650 °C / 0.01 Torr With lithium diisopropyl amide in tetrahydrofuran Aitken, R. Alan; Thomas, Andrew W.; Synlett; vol. 1997; nb. 3; (1997); p. 293 - 294 View in Reaxys

Rx-ID: 4471203 View in Reaxys 148/344 Yield

Conditions & References in benzene, Irradiation, also in the presence of the butanethiol, Quantum yield Wagner, Peter J.; Sedon, James H.; Gudmundsdottir, Anna; Journal of the American Chemical Society; vol. 118; nb. 4; (1996); p. 746 - 754 View in Reaxys

O Br

Rx-ID: 4488943 View in Reaxys 149/344 Yield

Conditions & References in benzene, Irradiation, photokinetics, Quantum yield Wagner, Peter J.; Sedon, James H.; Gudmundsdottir, Anna; Journal of the American Chemical Society; vol. 118; nb. 4; (1996); p. 746 - 754 View in Reaxys

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Rx-ID: 4626201 View in Reaxys 150/344 Yield

Conditions & References

90 %

With bis-triphenylphosphine-palladium(II) chloride, oxygen in toluene, Heating Linderman, Russell J.; Siedlecki, James M.; Journal of Organic Chemistry; vol. 61; nb. 19; (1996); p. 6492 - 6493 View in Reaxys

O O O

O O

Rx-ID: 4626202 View in Reaxys 151/344 Yield

Conditions & References

42 %, 39 %, With bis-triphenylphosphine-palladium(II) chloride in toluene, Heating 57 % Linderman, Russell J.; Siedlecki, James M.; Journal of Organic Chemistry; vol. 61; nb. 19; (1996); p. 6492 - 6493 View in Reaxys

Cl HO

Rx-ID: 5065838 View in Reaxys 152/344 Yield 56 %

Conditions & References With naphthalene, lithium in tetrahydrofuran, Time= 0.25h, T= 0 - 20 °C , Alkylation Alonso, Francisco; Lorenzo, Emilio; Yus, Miguel; Journal of Organic Chemistry; vol. 61; nb. 17; (1996); p. 6058 - 6059

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View in Reaxys

decacarbonyldimanganese O

Rx-ID: 7159950 View in Reaxys 153/344 Yield

Conditions & References With N,N,N,N,N,N-hexamethylphosphoric triamide, Yield given. Multistep reaction Yamamoto, Hiroshi M.; Sakurai, Hidehiro; Narasaka, Koichi; Bulletin of the Chemical Society of Japan; vol. 69; nb. 1; (1996); p. 157 - 161 View in Reaxys

Li Cl

Rx-ID: 4084583 View in Reaxys 154/344 Yield

Conditions & References 1.) 0 deg C, THF/hexane, 30 min 2.) 0 deg C r.t., THF/hexane, 1 h, Yield given. Multistep reaction Han, Ying; Fang, Lei; Tao, Wen-Tian; Huang, Yao-Zeng; Tetrahedron Letters; vol. 36; nb. 8; (1995); p. 1287 - 1290 View in Reaxys

Li+ Cl

Ga –

Rx-ID: 4084732 View in Reaxys 155/344 Yield

Conditions & References

83 %

in tetrahydrofuran, hexane, Time= 1h, T= 0 °C , to room temperature Han, Ying; Fang, Lei; Tao, Wen-Tian; Huang, Yao-Zeng; Tetrahedron Letters; vol. 36; nb. 8; (1995); p. 1287 - 1290 View in Reaxys

–

Rx-ID: 4159819 View in Reaxys 156/344

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Yield

Conditions & References With 1,2-bis(4-methoxyphenyl)ethene, tetrabutylammonium acetate in acetonitrile, Irradiation Mathivanan, N.; Johnston, L. J.; Wayner, D.D.M.; Journal of Physical Chemistry; vol. 99; nb. 20; (1995); p. 8190 - 8195 View in Reaxys

–

O O

N P

Br N

Rx-ID: 1624807 View in Reaxys 157/344 Yield

Conditions & References Irradiation, Rate constant Kimura, Norio; Takamuku, Setsuo; Journal of the American Chemical Society; vol. 116; nb. 9; (1994); p. 4087 - 4088 View in Reaxys O –

O O P N

Rx-ID: 1624808 View in Reaxys 158/344 Yield

Conditions & References Irradiation, Rate constant Kimura, Norio; Takamuku, Setsuo; Journal of the American Chemical Society; vol. 116; nb. 9; (1994); p. 4087 - 4088 View in Reaxys O O NH

O Cl

Rx-ID: 1661988 View in Reaxys 159/344 Yield

Conditions & References With tetrakis(triphenylphosphine) palladium(0), tri-n-butyl-tin hydride, triphenylphosphine, lithium diisopropyl amide, diethylazodicarboxylate, Yield given. Multistep reaction. Yields of byproduct given Ye; Bhatt; Falck; Journal of the American Chemical Society; vol. 116; nb. 1; (1994); p. 1 - 5 View in Reaxys

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O S

Rx-ID: 3718290 View in Reaxys 160/344 Yield

Conditions & References With tert.-butyl lithium in tetrahydrofuran, T= -70 °C , Yield given. Yields of byproduct given Satoh, Tsuyoshi; Itoh, Norifumi; Gengyo, Kaoru; Takada, Sae; Asakawa, Naoyuki; et al.; Tetrahedron; vol. 50; nb. 41; (1994); p. 11839 - 11852 View in Reaxys

O S

Rx-ID: 3718291 View in Reaxys 161/344 Yield

O O

Rx-ID: 3945850 View in Reaxys 162/344 Yield 66 % Chromat., 12 % Chromat., 22 % Chromat.

Conditions & References With lithium in tetrahydrofuran, Time= 2h, Ambient temperature, Irradiation, other n-butyl halides, var. time and frequency of sonication, Product distribution Danhui, Yang; Einhorn, Jacques; Einhorn, Cathy; Aurell, M. Jose; Luche, Jean-Louis; Journal of the Chemical Society, Chemical Communications; nb. 15; (1994); p. 1815 - 1816 View in Reaxys

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O–

Li+

Rx-ID: 3956131 View in Reaxys 163/344 Yield 94 % Chromat., 3 % Chromat.

Conditions & References With lithium in tetrahydrofuran, Time= 0.75h, Ambient temperature, Irradiation Danhui, Yang; Einhorn, Jacques; Einhorn, Cathy; Aurell, M. Jose; Luche, Jean-Louis; Journal of the Chemical Society, Chemical Communications; nb. 15; (1994); p. 1815 - 1816 View in Reaxys

O HO

Cl HO

Rx-ID: 3995111 View in Reaxys 164/344 Yield 66 % Chromat., 18 % Chromat.

Conditions & References With lithium in tetrahydrofuran, Time= 1.5h, Ambient temperature, Irradiation Danhui, Yang; Einhorn, Jacques; Einhorn, Cathy; Aurell, M. Jose; Luche, Jean-Louis; Journal of the Chemical Society, Chemical Communications; nb. 15; (1994); p. 1815 - 1816 View in Reaxys

O– Li+ O

Rx-ID: 18187649 View in Reaxys 165/344 Yield

Conditions & References Reaction Steps: 2 1: 3 percent Chromat. / Li / tetrahydrofuran / 0.75 h / Ambient temperature; Irradiation 2: 66 percent Chromat. / Li / tetrahydrofuran / 1.5 h / Ambient temperature; Irradiation With lithium in tetrahydrofuran Danhui, Yang; Einhorn, Jacques; Einhorn, Cathy; Aurell, M. Jose; Luche, Jean-Louis; Journal of the Chemical Society, Chemical Communications; nb. 15; (1994); p. 1815 - 1816 View in Reaxys Reaction Steps: 2 1: 40 percent Chromat. / nBuI, Li / tetrahydrofuran / 3.17 h / Ambient temperature; Irradiation 2: 66 percent Chromat. / Li / tetrahydrofuran / 1.5 h / Ambient temperature; Irradiation With 1-iodo-butane, lithium in tetrahydrofuran Danhui, Yang; Einhorn, Jacques; Einhorn, Cathy; Aurell, M. Jose; Luche, Jean-Louis; Journal of the Chemical Society, Chemical Communications; nb. 15; (1994); p. 1815 - 1816

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View in Reaxys

polymer-PPh2 (1+)-CH2-Ph*Br(1-) O

Rx-ID: 18393771 View in Reaxys 166/344 Yield

Conditions & References Reaction Steps: 2 1: 44 percent / 1.) LDA / tetrahydrofuran / 0.42 h / -65 °C 2: 4 eq. t-BuLi / tetrahydrofuran / -70 °C With tert.-butyl lithium, lithium diisopropyl amide in tetrahydrofuran Satoh, Tsuyoshi; Itoh, Norifumi; Gengyo, Kaoru; Takada, Sae; Asakawa, Naoyuki; et al.; Tetrahedron; vol. 50; nb. 41; (1994); p. 11839 - 11852 View in Reaxys Reaction Steps: 2 1: 38 percent / 1.) LDA / tetrahydrofuran / 0.42 h / -65 °C 2: 4 eq. t-BuLi / tetrahydrofuran / -70 °C With tert.-butyl lithium, lithium diisopropyl amide in tetrahydrofuran Satoh, Tsuyoshi; Itoh, Norifumi; Gengyo, Kaoru; Takada, Sae; Asakawa, Naoyuki; et al.; Tetrahedron; vol. 50; nb. 41; (1994); p. 11839 - 11852 View in Reaxys

O I–

N O

N+

Rx-ID: 1673901 View in Reaxys 167/344 Yield 66 %

Conditions & References in tetrahydrofuran, Time= 0.75h, T= -78 °C Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

I–

N+

Rx-ID: 1675172 View in Reaxys 168/344 Yield 85 %

Conditions & References in tetrahydrofuran, Time= 0.75h, T= -78 °C

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Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

I–

N+

O O

Rx-ID: 1675175 View in Reaxys 169/344 Yield

Conditions & References

77 %

in tetrahydrofuran, Time= 0.75h, T= -78 °C Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

I–

N+

Rx-ID: 1675176 View in Reaxys 170/344 Yield

Conditions & References

60 %

Li N

N O F HN O

F HO F F F

Rx-ID: 1750904 View in Reaxys 171/344 Yield

Conditions & References With foscarnet, 1.) ether, hexane, a) -78 deg C, 15 min., b) 0 deg C, 30 min., 2.) ether, hexane, a) 0 deg C, 1 h, b) RT, 5 h, Multistep reaction. Yields of byproduct given

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Reinecke, Manfred G.; Chen, Lao-Jer; Acta Chemica Scandinavica; vol. 47; nb. 3; (1993); p. 318 - 322 View in Reaxys With foscarnet, 1.) ether, hexane, a) -78 deg C, 15 min., b) 0 deg C, 30 min., 2.) ether, hexane, a) 0 deg C, 1 h, b) RT, 5 h, Yield given. Multistep reaction. Title compound not separated from byproducts Reinecke, Manfred G.; Chen, Lao-Jer; Acta Chemica Scandinavica; vol. 47; nb. 3; (1993); p. 318 - 322 View in Reaxys

F N

N O F HN

F HO F F F

Rx-ID: 1750910 View in Reaxys 172/344 Yield

Conditions & References With n-butyllithium, 1.) ether, hexane, a) -78 deg C, 15 min., b) 0 deg C, 30 min., 2.) ether, hexane, a) 0 deg C, 1 h, b) RT, 5 h, Multistep reaction. Yields of byproduct given Reinecke, Manfred G.; Chen, Lao-Jer; Acta Chemica Scandinavica; vol. 47; nb. 3; (1993); p. 318 - 322 View in Reaxys

F O

F F

Rx-ID: 1750911 View in Reaxys 173/344 Yield

Conditions & References With hydrogenchloride, n-butyllithium, Multistep reaction Reinecke, Manfred G.; Chen, Lao-Jer; Acta Chemica Scandinavica; vol. 47; nb. 3; (1993); p. 318 - 322 View in Reaxys

O O

Mg Cl

Rx-ID: 2705210 View in Reaxys 174/344 Yield

Conditions & References With ethanol, 1) THF, -78 deg C, 18 h, 2) r.t., 24 h, Yield given. Multistep reaction. Yields of byproduct given

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Kauffmann, Thomas; Voss, Karl-Uwe; Neiteler, Gabriele; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1453 - 1460 View in Reaxys

O (v2)

O Cl

Rx-ID: 2707487 View in Reaxys 175/344 Yield

Conditions & References With ethanol, 1) THF, -78 deg C, 18 h, 2) r.t., 24 h, Yield given. Multistep reaction. Yields of byproduct given Kauffmann, Thomas; Voss, Karl-Uwe; Neiteler, Gabriele; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1453 - 1460 View in Reaxys

N+ N N

I–

Rx-ID: 3640112 View in Reaxys 176/344 Yield 85 %, 80 %

Conditions & References With n-butyllithium in tetrahydrofuran, Time= 0.75h, T= -78 °C Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

nBu4FeLi2 Cl

Rx-ID: 7159952 View in Reaxys 177/344 Yield

Conditions & References With ethanol, 1) THF, -78 deg C, 18 h, 2) r.t., 24 h, Yield given. Multistep reaction Kauffmann, Thomas; Voss, Karl-Uwe; Neiteler, Gabriele; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1453 - 1460 View in Reaxys

O O

Bu3FeLi Cl

Rx-ID: 7160262 View in Reaxys 178/344

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Yield

–O

N+

Rx-ID: 18731453 View in Reaxys 179/344 Yield

Conditions & References Reaction Steps: 2 1: 88 percent / acetone / 12 h / Heating 2: 66 percent / tetrahydrofuran / 0.75 h / -78 °C in tetrahydrofuran, acetone Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

(S)-2-chloro-butyric acid Cl

Rx-ID: 18741561 View in Reaxys 180/344 Yield

Conditions & References Reaction Steps: 3 1: 68 percent / K2CO3 / CH2Cl2 / 6 h / Heating 2: 80 percent / acetone / 24 h / Ambient temperature 3: 77 percent / tetrahydrofuran / 0.75 h / -78 °C With potassium carbonate in tetrahydrofuran, dichloromethane, acetone Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys Reaction Steps: 3 1: 83 percent / K2CO3 / CH2Cl2 / 6 h / Heating 2: 90 percent / ethyl acetate / 24 h / Ambient temperature 3: 60 percent / tetrahydrofuran / 0.75 h / -78 °C With potassium carbonate in tetrahydrofuran, dichloromethane, ethyl acetate Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys Reaction Steps: 2 1: 57 percent / K2CO3 / CH2Cl2 / 1.) room temp., 15 min, 2.) reflux, 6 h 2: 85 percent / tetrahydrofuran / 0.75 h / -78 °C With potassium carbonate in tetrahydrofuran, dichloromethane

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Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys Reaction Steps: 2 1: 57 percent / K2CO3 / CH2Cl2 / 1.) room temp., 15 min, 2.) reflux, 6 h 2: 85 percent / n-BuLi / tetrahydrofuran / 0.75 h / -78 °C With n-butyllithium, potassium carbonate in tetrahydrofuran, dichloromethane Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys Reaction Steps: 3 1: 83 percent / K2CO3 / CH2Cl2 / 6 h / Heating 2: 95 percent / ethyl acetate / 24 h / Ambient temperature 3: 85 percent / tetrahydrofuran / 0.75 h / -78 °C With potassium carbonate in tetrahydrofuran, dichloromethane, ethyl acetate Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys Reaction Steps: 3 1: 83 percent / K2CO3 / CH2Cl2 / 6 h / Heating 2: 95 percent / ethyl acetate / 24 h / Ambient temperature 3: 85 percent / n-BuLi / tetrahydrofuran / 0.75 h / -78 °C With n-butyllithium, potassium carbonate in tetrahydrofuran, dichloromethane, ethyl acetate Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

–O

N N+

Rx-ID: 18753680 View in Reaxys 181/344 Yield

Conditions & References Reaction Steps: 2 1: 95 percent / ethyl acetate / 24 h / Ambient temperature 2: 85 percent / tetrahydrofuran / 0.75 h / -78 °C in tetrahydrofuran, ethyl acetate Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys Reaction Steps: 2 1: 95 percent / ethyl acetate / 24 h / Ambient temperature 2: 85 percent / n-BuLi / tetrahydrofuran / 0.75 h / -78 °C With n-butyllithium in tetrahydrofuran, ethyl acetate Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

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N N+

O O–

Rx-ID: 18754800 View in Reaxys 182/344 Yield

Conditions & References Reaction Steps: 2 1: 80 percent / acetone / 24 h / Ambient temperature 2: 77 percent / tetrahydrofuran / 0.75 h / -78 °C in tetrahydrofuran, acetone Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

N O– N+

Rx-ID: 18756237 View in Reaxys 183/344 Yield

Conditions & References Reaction Steps: 2 1: 90 percent / ethyl acetate / 24 h / Ambient temperature 2: 60 percent / tetrahydrofuran / 0.75 h / -78 °C in tetrahydrofuran, ethyl acetate Heras, Maria A. de las; Molina, Andres; Vaquero, Juan J.; Navio, Jose L. Garcia; Alvarez-Builla, Julio; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5862 - 5865 View in Reaxys

Cl Mg

Rx-ID: 2707482 View in Reaxys 184/344 Yield 85 %

Conditions & References With lithium tetrachloromanganate(II) in tetrahydrofuran, Time= 0.166667h, T= 0 °C Cahiez, Gerard; Tetrahedron Letters; vol. 33; nb. 31; (1992); p. 4439 - 4442 View in Reaxys With zinc(II) chloride, (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride, 1) THF, 2 hr, r.t. 2) THF a) 2 hr 0 deg C b) 2 hr , 23 deg C, Yield given. Multistep reaction Grey, Roger A.; Journal of Organic Chemistry; vol. 49; nb. 12; (1984); p. 2288 - 2289 View in Reaxys

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Sb Cl

Rx-ID: 2707969 View in Reaxys 185/344 Yield 92 %

Conditions & References in tetrahydrofuran, Ambient temperature Zhang, Li-Jun; Huang, Yao-Zeng; Jiang, Hong-Xia; Duan-Mu, Jun; Liao, Yi; Journal of Organic Chemistry; vol. 57; nb. 2; (1992); p. 774 - 777 View in Reaxys

Rx-ID: 2709981 View in Reaxys 186/344 Yield 25 %, 62 %

O S

Rx-ID: 2776192 View in Reaxys 187/344 Yield

Conditions & References With tert.-butyl lithium in tetrahydrofuran, T= -60 °C , Yield given. Yields of byproduct given Satoh, Tsuyoshi; Itoh, Norifumi; Gengyo, Kaoru; Yamakawa, Koji; Tetrahedron Letters; vol. 33; nb. 49; (1992); p. 7543 7546 View in Reaxys

Cl +Mg

Cl –

Rx-ID: 2909594 View in Reaxys 188/344

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Yield

Conditions & References

85 %

With lithium tetrachloromanganate(II) in tetrahydrofuran, Time= 0.166667h, T= 0 - 10 °C Cahiez, Gerard; Tetrahedron Letters; vol. 33; nb. 31; (1992); p. 4439 - 4442 View in Reaxys

aminoguanidine salt O

Rx-ID: 19686918 View in Reaxys 189/344 Yield

Conditions & References Reaction Steps: 2 2: t-BuLi / tetrahydrofuran / -60 °C With tert.-butyl lithium in tetrahydrofuran Satoh, Tsuyoshi; Itoh, Norifumi; Gengyo, Kaoru; Yamakawa, Koji; Tetrahedron Letters; vol. 33; nb. 49; (1992); p. 7543 7546 View in Reaxys

Si N N O

Rx-ID: 1818350 View in Reaxys 190/344 Yield

Conditions & References With 2,2,6,6-tetramethyl-piperidine, sec.-butyllithium, 1) THF, dry ice bath, 0.5 h, 2) THF, ice cooling, 1 h, Yield given. Multistep reaction. Yields of byproduct given Whitney, Scott E.; Rickborn, Bruce; Journal of Organic Chemistry; vol. 56; (1991); p. 3058 - 3063 View in Reaxys

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N Cl Si

Si N N O

Rx-ID: 1818352 View in Reaxys 191/344 Yield

Conditions & References With 2,2,6,6-tetramethyl-piperidine, sec.-butyllithium, solvent:1a) THF, dry ice bath, b) ice cooling, Yield given. Multistep reaction. Yields of byproduct given Whitney, Scott E.; Rickborn, Bruce; Journal of Organic Chemistry; vol. 56; (1991); p. 3058 - 3063 View in Reaxys

N N O

Rx-ID: 1818368 View in Reaxys 192/344 Yield

Conditions & References With n-butyllithium, water, 1) THF, dry ice bath, 0.5 h, 2) THF, ice cooling, 1 h, Yield given. Multistep reaction. Yields of byproduct given Whitney, Scott E.; Rickborn, Bruce; Journal of Organic Chemistry; vol. 56; (1991); p. 3058 - 3063 View in Reaxys With n-butyllithium, water, 1) THF, 0.5 h, 2) THF, 1 h, Multistep reaction. Yields of byproduct given Whitney, Scott E.; Rickborn, Bruce; Journal of Organic Chemistry; vol. 56; (1991); p. 3058 - 3063 View in Reaxys

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With n-butyllithium, water, 1) THF, dry ice bath, 0.5 h, 2) ice cooling, THF, 1 h, Yield given. Multistep reaction. Yields of byproduct given Whitney, Scott E.; Rickborn, Bruce; Journal of Organic Chemistry; vol. 56; (1991); p. 3058 - 3063 View in Reaxys

N Li

Rx-ID: 1673414 View in Reaxys 193/344 Yield 31 %

Conditions & References in tetrahydrofuran, hexane, Time= 0.5h, T= -78 °C Beak, Peter; Brown, Roger A.; Journal of Organic Chemistry; vol. 47; nb. 1; (1982); p. 34 - 46 View in Reaxys With lanthanum(lll) triflate, 1.) Et2O, -78 deg C then up to 0 deg C, 2.) -30 deg C, 30 min, Yield given. Multistep reaction Collins, Scott; Hong, Yaping; Hoover, Gordon J.; Veit, Jennifer R.; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3565 - 3568 View in Reaxys With lithium bromide, lanthanum(lll) triflate, ether, -78 deg C, 30 min, Yield given. Multistep reaction Collins, Scott; Hong, Yaping; Tetrahedron Letters; vol. 28; nb. 38; (1987); p. 4391 - 4394 View in Reaxys

Rx-ID: 1970376 View in Reaxys 194/344 Yield

Conditions & References With Cumene hydroperoxide in o-xylene, Time= 40h, T= 120 °C , Yield given. Yields of byproduct given Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

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Rx-ID: 2012178 View in Reaxys 195/344 Yield

Conditions & References With Cumene hydroperoxide, Time= 10h, T= 120 °C , Yield given. Further byproducts given. Yields of byproduct given Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

H+

–C

Rx-ID: 2230771 View in Reaxys 196/344 Yield

Conditions & References

79 %

With hydrogenchloride in chloroform, Heating Jones, Raymond C. F.; Nichols, John R.; Tetrahedron Letters; vol. 31; nb. 12; (1990); p. 1771 - 1774 View in Reaxys

(v2)

Cl –

Li+

Rx-ID: 2707412 View in Reaxys 197/344 Yield 77 %

Conditions & References in tetrahydrofuran, Time= 18h, -70 deg C to r.t. Kauffmann, Thomas; Laarmann, Barbara; Menges, Detlef; Voss, Karl-Uwe; Wingbermuehle, Dorothea; Tetrahedron Letters; vol. 31; nb. 4; (1990); p. 507 - 510 View in Reaxys

(v2)

Br–

Cl –

Mg2+

Rx-ID: 2707446 View in Reaxys 198/344

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Yield 94 %

Rx-ID: 21796678 View in Reaxys 199/344 Yield

Conditions & References Reaction Steps: 2 1: cumene hydroperoxide / 10 h / 120 °C 2: cumene hydroperoxide / o-xylene / 40 h / 120 °C With Cumene hydroperoxide in o-xylene Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

Cu (v1)

Rx-ID: 2707477 View in Reaxys 200/344 Yield 100 %

Conditions & References With lithium iodide in various solvent(s), -78 deg C, 0.5 h, 0 deg C, 0.5 h Bertz, Steven H.; Dabbagh, Gary; Tetrahedron; vol. 45; nb. 2; (1989); p. 425 - 434 View in Reaxys

Cl Mn (v2)

Rx-ID: 2707993 View in Reaxys 201/344 Yield 90 %

Conditions & References in tetrahydrofuran, T= -10 - 20 °C Cahiez, Gerard; Laboue, Blandine; Tetrahedron Letters; vol. 30; nb. 52; (1989); p. 7369 - 7372 View in Reaxys

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O O

Rx-ID: 2924937 View in Reaxys 202/344 Yield 60 %

Conditions & References in tetrahydrofuran, diethyl ether, hexane, cyclohexane, 1) -78 deg C, 1 h; 2) from -78 deg C to room temperature, 2 h Hlasta, Dennis J.; Court, John J.; Tetrahedron Letters; vol. 30; nb. 14; (1989); p. 1773 - 1776 View in Reaxys

O O

–O

S O

Rx-ID: 3021224 View in Reaxys 203/344 Yield 84 % Chromat.

Conditions & References With potassium superoxide in acetonitrile, Time= 6h, T= -35 °C Kim, Yong Hae; Kim, Kyoung Soo; Lee, Hyeon Kyu; Tetrahedron Letters; vol. 30; nb. 46; (1989); p. 6357 - 6360 View in Reaxys

Rx-ID: 3878720 View in Reaxys 204/344 Yield

Conditions & References With rhodium(II) acetate in toluene, T= 102 °C , Product distribution Doyle, Michael P.; High, Kenneth G.; Oon, Su-Min; Osborn, Antonio K.; Tetrahedron Letters; vol. 30; nb. 23; (1989); p. 3049 - 3052 View in Reaxys

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Rx-ID: 3878721 View in Reaxys 205/344 Yield

Conditions & References in toluene, T= 102 °C , Further byproducts given Doyle, Michael P.; High, Kenneth G.; Oon, Su-Min; Osborn, Antonio K.; Tetrahedron Letters; vol. 30; nb. 23; (1989); p. 3049 - 3052 View in Reaxys

O Se

(C4H9)2CuLi

O O

Rx-ID: 7159949 View in Reaxys 206/344 Yield 79 %

Conditions & References in benzene, Time= 0.166667h, T= 25 °C Nishiyama, Yutaka; Katsuura, Akio; Okamoto, Youji; Hamanaka, Sawako; Chemistry Letters; (1989); p. 1825 - 1826 View in Reaxys

(v5)

Rx-ID: 1781783 View in Reaxys 207/344 Yield 6 %, 45 %, 47 %

Conditions & References With tetrakis(triphenylphosphine)platinum in 1,4-dioxane, Time= 24h, T= 130 °C , several catalysts and conditions investigated, Product distribution, Mechanism Kondo, Teruyuki; Tsuji, Yasushi; Watanabe, Yoshihisa; Journal of Organometallic Chemistry; vol. 345; (1988); p. 397 - 404 View in Reaxys

6 %, 45 %, 47 %

With tetrakis(triphenylphosphine)platinum in 1,4-dioxane, T= 130 °C Kondo, Teruyuki; Tsuji, Yasushi; Watanabe, Yoshihisa; Journal of Organometallic Chemistry; vol. 345; (1988); p. 397 - 404 View in Reaxys

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O I Cl

Rx-ID: 2705584 View in Reaxys 208/344 Yield

Conditions & References Yield given. Multistep reaction Knochel, Paul; Yeh, Ming Chang P.; Berk, Scott C.; Talbert Jason; Journal of Organic Chemistry; vol. 53; nb. 10; (1988); p. 2390 - 2392 View in Reaxys

1.) disodium tetracarbonylferrat O

Rx-ID: 7159947 View in Reaxys 209/344 Yield

Conditions & References 1.) N-methyl-2-pyrrolidone, PPh3, r.t, 2 h; 2.) C6H6, THF, Pd(PPh3)4, ZnCl2, r.t., 3 h, Yield given. Multistep reaction Koga, Teruyoshi; Makinouchi, Shinako; Okukado, Nobuhisa; Chemistry Letters; (1988); p. 1141 - 1144 View in Reaxys

N O

Rx-ID: 1673496 View in Reaxys 210/344 Yield

Conditions & References With hydrogenchloride, ether, room temp., 4h, Yield given. Multistep reaction Tominaga, Yoshinori; Kohra, Shinya; Hosomi, Akira; Tetrahedron Letters; vol. 28; nb. 14; (1987); p. 1529 - 1532 View in Reaxys

S Li

Rx-ID: 1800631 View in Reaxys 211/344 Yield

Conditions & References With hydrogenchloride, 1.) ether, room temp., 4h, Yield given. Multistep reaction Tominaga, Yoshinori; Kohra, Shinya; Hosomi, Akira; Tetrahedron Letters; vol. 28; nb. 14; (1987); p. 1529 - 1532

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View in Reaxys

O N N

Rx-ID: 2567199 View in Reaxys 212/344 Yield

Conditions & References With potassium carbonate, 3-chloro-benzenecarboperoxoic acid, 1.) CH2Cl2; 2.) CH2Cl2, 3 h, Product distribution Ohta, Shunsaku; Hayakawa, Satoshi; Nishimura, Kazuko; Okamoto, Masao; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 3; (1987); p. 1058 - 1069 View in Reaxys Reaction Steps: 2 1: ethyl acetate 2: 10 percent potassium carbonate / benzene With potassium carbonate in ethyl acetate, benzene Ohta, Shunsaku; Hayakawa, Satoshi; Nishimura, Kazuko; Okamoto, Masao; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 3; (1987); p. 1058 - 1069 View in Reaxys Reaction Steps: 2 1: ethyl acetate / 2 h / Heating 2: K2CO3 / benzene / 2 h / 60 °C With potassium carbonate in ethyl acetate, benzene Ohta, Shunsaku; Hayakawa, Satoshi; Nishimura, Kazuko; Okamoto, Masao; Tetrahedron Letters; vol. 25; nb. 30; (1984); p. 3251 - 3254 View in Reaxys Reaction Steps: 2 1: ethyl acetate / 2 h / Heating 2: 86 percent / aq. ethanol / 72 h / Heating in ethanol, ethyl acetate Ohta, Shunsaku; Hayakawa, Satoshi; Nishimura, Kazuko; Okamoto, Masao; Tetrahedron Letters; vol. 25; nb. 30; (1984); p. 3251 - 3254 View in Reaxys

N I– HO

N+

O N N

Rx-ID: 2567200 View in Reaxys 213/344 Yield 86 %, 63 %

Conditions & References With methyl iodide in ethyl acetate, Time= 72h, Heating Ohta, Shunsaku; Hayakawa, Satoshi; Nishimura, Kazuko; Okamoto, Masao; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 3; (1987); p. 1058 - 1069

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View in Reaxys

I–

N+

O N N+

Rx-ID: 2633680 View in Reaxys 214/344 Yield 86 %, 63 %

Conditions & References in ethanol, Time= 72h, Heating Ohta, Shunsaku; Hayakawa, Satoshi; Nishimura, Kazuko; Okamoto, Masao; Tetrahedron Letters; vol. 25; nb. 30; (1984); p. 3251 - 3254 View in Reaxys With potassium carbonate in benzene, Yield given Ohta, Shunsaku; Hayakawa, Satoshi; Nishimura, Kazuko; Okamoto, Masao; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 3; (1987); p. 1058 - 1069 View in Reaxys

Rx-ID: 2707888 View in Reaxys 215/344 Yield 99 %

Conditions & References With tetrakis(triphenylphosphine) palladium(0) in benzene, Time= 6h, Heating, different acid chlorides, tetra-alkyl-lead derivative, ratios of reactant, catalyst, solvents, reaction temperature and times, Product distribution Yamada, Jun-ichi; Yamamoto, Yoshinori; Journal of the Chemical Society, Chemical Communications; nb. 17; (1987); p. 1302 - 1303 View in Reaxys

99 %

With tetrakis(triphenylphosphine) palladium(0) in benzene, Time= 6h, Heating Yamada, Jun-ichi; Yamamoto, Yoshinori; Journal of the Chemical Society, Chemical Communications; nb. 17; (1987); p. 1302 - 1303 View in Reaxys

Li(CH3SOCH2Cun-Bu) Cl

Rx-ID: 7159951 View in Reaxys 216/344 Yield 90 %

Conditions & References in tetrahydrofuran, Time= 1h, T= -78 °C

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Johnson, Carl R.; Dhanoa, Daljit S.; Journal of Organic Chemistry; vol. 52; nb. 10; (1987); p. 1885 - 1888 View in Reaxys

O N

Rx-ID: 1608146 View in Reaxys 217/344 Yield

Conditions & References

68 %

in tetrahydrofuran, dichloromethane, T= 0 °C Miyasaka, Tadayo; Monobe, Hideaki; Noguchi, Shunsaku; Chemistry Letters; (1986); p. 449 - 452 View in Reaxys O

O HO

O OH

Rx-ID: 1673103 View in Reaxys 218/344 Yield 9 %, 42 %, 31 %

Conditions & References With bis(tetra-n-butylammonium) tetrakis(benzenethiolato-.mu.3-sulfidoiron) in diethyl ether, hexane, Time= 20h, Ambient temperature Inoue, Hiroo; Nagata, Tadashi; Journal of the Chemical Society, Chemical Communications; nb. 15; (1986); p. 1177 - 1178 View in Reaxys

9 %, 42 %, 31 %

With bis(tetra-n-butylammonium) tetrakis(benzenethiolato-.mu.3-sulfidoiron) in diethyl ether, Time= 20h, Ambient temperature Inoue, Hiroo; Nagata, Tadashi; Journal of the Chemical Society, Chemical Communications; nb. 15; (1986); p. 1177 - 1178 View in Reaxys

O Si

Rx-ID: 1673454 View in Reaxys 219/344 Yield 72 %

Conditions & References in tetrahydrofuran, diethyl ether, Time= 1h, T= 0 °C Itsuno, Shinichi; Miyazaki, Koji; Ito, Koichi; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 3033 - 3036 View in Reaxys

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O HO

O OH

Rx-ID: 1673515 View in Reaxys 220/344 Yield 6 %, 15 %, 42 %

O N Li

Rx-ID: 1673575 View in Reaxys 221/344 Yield 81 %

Conditions & References in tetrahydrofuran, diethyl ether, Time= 1h, T= -78 °C Itsuno, Shinichi; Miyazaki, Koji; Ito, Koichi; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 3033 - 3036 View in Reaxys

O N N

Rx-ID: 1673577 View in Reaxys 222/344 Yield

Conditions & References T= 0 °C Itsuno, Shinichi; Miyazaki, Koji; Ito, Koichi; Tetrahedron Letters; vol. 27; nb. 26; (1986); p. 3033 - 3036 View in Reaxys

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O N

Rx-ID: 1673578 View in Reaxys 223/344 Yield 80 %

O (v2)

Cu – Li+

Rx-ID: 2069287 View in Reaxys 224/344 Yield 97 %

Conditions & References in tetrahydrofuran, diethyl ether, Time= 0.5h, T= -78 °C Sasaki, Kazuaki; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio; Chemistry Letters; (1986); p. 977 - 978 View in Reaxys

O S

Rx-ID: 2584553 View in Reaxys 225/344 Yield

Conditions & References With mercury(II) diacetate, 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature, Yield given. Multistep reaction Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

Rx-ID: 2681332 View in Reaxys 226/344 Yield 39 %, 15 %

Conditions & References With lithium (1R,2S,5R)-menthoxide in methyl cyclohexane, T= -60 - 0 °C , effect of lithium alkoxides and reactant ratios, Product distribution

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Screttas, Constantinos G.; Steele, Barry R.; Journal of Organometallic Chemistry; vol. 317; (1986); p. 137 - 144 View in Reaxys 39 % Chromat., 15 % Chromat.

With lithium 1-phenylpentyloxide in methyl cyclohexane Screttas, Constantinos G.; Steele, Barry R.; Journal of Organometallic Chemistry; vol. 317; (1986); p. 137 - 144 View in Reaxys

O O O O

Rx-ID: 3155909 View in Reaxys 227/344 Yield

Conditions & References in diphenylether, T= 147.2 °C , Ea, log A, other temp., Thermodynamic data, Kinetics, Rate constant Ito, Yoshikatsu; Tone, Mutsuo; Yokoya, Hiroaki; Matsuura, Teruo; Schuster, Gary B.; Journal of Organic Chemistry; vol. 51; nb. 12; (1986); p. 2240 - 2245 View in Reaxys

O O

Rx-ID: 3155911 View in Reaxys 228/344 Yield 2 % Chromat., 97 % Chromat.

Conditions & References With zinc tetraphenylporphyrin in various solvent(s), Time= 10h, other cyclic diperoxides, CoTPP, p-substituted ZnTPP, added Ph2SO, Ph2S, var. solvents, time, temperature, Rate constant, Product distribution, Mechanism Ito, Yoshikatsu; Tone, Mutsuo; Yokoya, Hiroaki; Matsuura, Teruo; Schuster, Gary B.; Journal of Organic Chemistry; vol. 51; nb. 12; (1986); p. 2240 - 2245 View in Reaxys

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Rx-ID: 20749939 View in Reaxys 229/344 Yield

Conditions & References Reaction Steps: 4 1: 89 percent / butyl-lithium / tetrahydrofuran; hexane / 0 - 20 °C 2: 75 percent / butyl-lithium, TMEDA / hexane / 0 °C 3: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 4: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With n-butyllithium, N,N,N,N,-tetramethylethylenediamine, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys Reaction Steps: 4 1: 89 percent / butyl-lithium / tetrahydrofuran; hexane / 0 - 20 °C 2: 85 percent / butyl-lithium, TMEDA / hexane / 0 °C 3: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 4: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With n-butyllithium, N,N,N,N,-tetramethylethylenediamine, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys Reaction Steps: 6 1: 89 percent / butyl-lithium / tetrahydrofuran; hexane / 0 - 20 °C 2: 93 percent / m-chloroperbenzoic acid / CH2Cl2 / -23 °C 3: 63 percent / butyl-lithium / hexane; tetrahydrofuran / 0 °C 4: 77 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating 5: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 6: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With lithium aluminium tetrahydride, n-butyllithium, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

O S

Rx-ID: 20750772 View in Reaxys 230/344 Yield

Conditions & References Reaction Steps: 5 1: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 1 h / 0 °C 2: 63 percent / butyl-lithium / hexane; tetrahydrofuran / 0 °C

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3: 77 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating 4: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 5: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With lithium aluminium tetrahydride, n-butyllithium, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

O S

Rx-ID: 20754279 View in Reaxys 231/344 Yield

Conditions & References Reaction Steps: 3 1: 75 percent / butyl-lithium, TMEDA / hexane / 0 °C 2: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 3: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With n-butyllithium, N,N,N,N,-tetramethylethylenediamine, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys Reaction Steps: 3 1: 85 percent / butyl-lithium, TMEDA / hexane / 0 °C 2: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 3: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With n-butyllithium, N,N,N,N,-tetramethylethylenediamine, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys Reaction Steps: 5 1: 93 percent / m-chloroperbenzoic acid / CH2Cl2 / -23 °C 2: 63 percent / butyl-lithium / hexane; tetrahydrofuran / 0 °C 3: 77 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating 4: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 5: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With lithium aluminium tetrahydride, n-butyllithium, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

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Rx-ID: 20754770 View in Reaxys 232/344 Yield

Conditions & References Reaction Steps: 5 1: 95 percent / ethanol 2: 89 percent / butyl-lithium / tetrahydrofuran; hexane / 0 - 20 °C 3: 75 percent / butyl-lithium, TMEDA / hexane / 0 °C 4: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 5: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With n-butyllithium, N,N,N,N,-tetramethylethylenediamine, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, ethanol, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys Reaction Steps: 5 1: 95 percent / ethanol 2: 89 percent / butyl-lithium / tetrahydrofuran; hexane / 0 - 20 °C 3: 85 percent / butyl-lithium, TMEDA / hexane / 0 °C 4: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 5: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With n-butyllithium, N,N,N,N,-tetramethylethylenediamine, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, ethanol, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys Reaction Steps: 7 1: 95 percent / ethanol 2: 89 percent / butyl-lithium / tetrahydrofuran; hexane / 0 - 20 °C 3: 93 percent / m-chloroperbenzoic acid / CH2Cl2 / -23 °C 4: 63 percent / butyl-lithium / hexane; tetrahydrofuran / 0 °C 5: 77 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating 6: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 7: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With lithium aluminium tetrahydride, n-butyllithium, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, ethanol, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

Rx-ID: 20756991 View in Reaxys 233/344

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Yield

Conditions & References Reaction Steps: 5 1: m-chloroperbenzoic acid / CH2Cl2 2: 48 percent / butyl-lithium / hexane; tetrahydrofuran / 1 h / 0 °C 3: 77 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating 4: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 5: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With lithium aluminium tetrahydride, n-butyllithium, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

Rx-ID: 20757277 View in Reaxys 234/344 Yield

Conditions & References Reaction Steps: 2 1: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 2: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

O S

Rx-ID: 20757456 View in Reaxys 235/344 Yield

Conditions & References Reaction Steps: 3 1: 1.) lithium naphthalenide 2: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 3: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With mercury(II) diacetate, naphthalen-1-yl-lithium, 3-chloro-benzenecarboperoxoic acid in dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

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O S O

Rx-ID: 20765086 View in Reaxys 236/344 Yield

Conditions & References Reaction Steps: 4 1: 48 percent / butyl-lithium / hexane; tetrahydrofuran / 1 h / 0 °C 2: 77 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating 3: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 4: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With lithium aluminium tetrahydride, n-butyllithium, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

O S

Rx-ID: 20768201 View in Reaxys 237/344 Yield

Conditions & References Reaction Steps: 3 1: 77 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating 2: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 3: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With lithium aluminium tetrahydride, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

Si O

S O O

Rx-ID: 20776608 View in Reaxys 238/344 Yield

Conditions & References Reaction Steps: 4 1: 63 percent / butyl-lithium / hexane; tetrahydrofuran / 0 °C 2: 77 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating 3: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C

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4: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature With lithium aluminium tetrahydride, n-butyllithium, mercury(II) diacetate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, hexane, dichloromethane Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 195 - 204 View in Reaxys

Br Mg

Br–

+Mg

Rx-ID: 1607755 View in Reaxys 239/344 Yield

Conditions & References With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride, iron(III)-acetylacetonate, 1) tetrahydrofurane, room temperature, 2) 0 deg C, Yield given. Multistep reaction Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 26; nb. 30; (1985); p. 3595 - 3598 View in Reaxys

O Br Mg

Rx-ID: 1607810 View in Reaxys 240/344 Yield

Conditions & References

85 %

With iron(III)-acetylacetonate in tetrahydrofuran, T= 0 °C Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 26; nb. 30; (1985); p. 3595 - 3598 View in Reaxys O

O O HO

Rx-ID: 1673804 View in Reaxys 241/344 Yield

Conditions & References in hexane, T= 0 °C , various organometallic compounds, various products by a SET mechanism, Mechanism, Product distribution Hendrickson, W. H.; MacDonald, W. D.; Howard, S. T.; Coligado, E. J.; Tetrahedron Letters; vol. 26; nb. 25; (1985); p. 2939 - 2942

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View in Reaxys O O O Li

Rx-ID: 1674153 View in Reaxys 242/344 Yield

Conditions & References

30 %, 36 %, in hexane, Time= 2h, T= 0 °C 26 %, 22 % Hendrickson, W. H.; MacDonald, W. D.; Howard, S. T.; Coligado, E. J.; Tetrahedron Letters; vol. 26; nb. 25; (1985); p. 2939 - 2942 View in Reaxys O

Li I

Rx-ID: 2117022 View in Reaxys 243/344 Yield

Conditions & References

25 %, 20 %, in tetrahydrofuran, T= 0 °C , Var.: -78 deg C 12 % Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys

HO I

Rx-ID: 2117025 View in Reaxys 244/344 Yield

Conditions & References

66 %, 7 % With tert.-butyl lithium in tetrahydrofuran, T= -78 °C , Var.: 0 deg C Chromat., 6 % Chromat. Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990

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View in Reaxys 25 %, 20 %, With tert.-butyl lithium in tetrahydrofuran, T= 0 °C 12 % Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys O

Rx-ID: 2255977 View in Reaxys 245/344 Yield 14 %, 2 %, 9 %, 86 %

Conditions & References in diethyl ether, Time= 2h, T= 0 °C Hendrickson, W. H.; MacDonald, W. D.; Howard, S. T.; Coligado, E. J.; Tetrahedron Letters; vol. 26; nb. 25; (1985); p. 2939 - 2942 View in Reaxys

Br Mg

Rx-ID: 2677718 View in Reaxys 246/344 Yield 54 %

Conditions & References With vanadium(III) chloride, 1.) dichloromethane/ether, -78 deg C, 2 h; 2.) toluene, reflux, 16 h Hirao, Toshikazu; Misu, Daisuke; Agawa, Toshio; Journal of the American Chemical Society; vol. 107; nb. 24; (1985); p. 7179 - 7181 View in Reaxys

Br–

+Mg

Rx-ID: 21470381 View in Reaxys 247/344 Yield

Conditions & References Reaction Steps: 2 1: 87 percent / dichloro<1,2-bis(diphenylphosphino)ethane>nickel(II) / tetrahydrofuran / Ambient temperature 2: 85 percent / tris(acetylacetonate)iron(III) / tetrahydrofuran / 0 °C With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride, iron(III)-acetylacetonate in tetrahydrofuran

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Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 26; nb. 30; (1985); p. 3595 - 3598 View in Reaxys

Rx-ID: 21553948 View in Reaxys 248/344 Yield

Conditions & References Reaction Steps: 4 2: pyridinium chlorochromate 3: NaI / acetone 4: 20 percent / tetrahydrofuran / 0 °C / Var.: -78 deg C With pyridinium chlorochromate, sodium iodide in tetrahydrofuran, acetone Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys Reaction Steps: 4 2: pyridinium chlorochromate 3: NaI / acetone 4: 20 percent / t-BuLi / tetrahydrofuran / 0 °C With tert.-butyl lithium, pyridinium chlorochromate, sodium iodide in tetrahydrofuran, acetone Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys

Rx-ID: 21555617 View in Reaxys 249/344 Yield

Conditions & References Reaction Steps: 2 1: NaI / acetone 2: 20 percent / tetrahydrofuran / 0 °C / Var.: -78 deg C With sodium iodide in tetrahydrofuran, acetone Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys Reaction Steps: 2 1: NaI / acetone 2: 20 percent / t-BuLi / tetrahydrofuran / 0 °C With tert.-butyl lithium, sodium iodide in tetrahydrofuran, acetone Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys

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Rx-ID: 21555643 View in Reaxys 250/344 Yield

Conditions & References Reaction Steps: 3 1: pyridinium chlorochromate 2: NaI / acetone 3: 20 percent / tetrahydrofuran / 0 °C / Var.: -78 deg C With pyridinium chlorochromate, sodium iodide in tetrahydrofuran, acetone Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys Reaction Steps: 3 1: pyridinium chlorochromate 2: NaI / acetone 3: 20 percent / t-BuLi / tetrahydrofuran / 0 °C With tert.-butyl lithium, pyridinium chlorochromate, sodium iodide in tetrahydrofuran, acetone Cooke, Manning P.; Houpis, Ioannis N.; Tetrahedron Letters; vol. 26; nb. 41; (1985); p. 4987 - 4990 View in Reaxys

Br Mg

Rx-ID: 609384 View in Reaxys 251/344 Yield 90 %

Conditions & References With iron(III)-acetylacetonate in tetrahydrofuran, Time= 0.166667h, Ambient temperature, a mild method for ketone praparation Fiandanese, V.; Marchese, G.; Martina, V.; Ronzini, L.; Tetrahedron Letters; vol. 25; nb. 42; (1984); p. 4805 - 4808 View in Reaxys

90 %

With iron(III)-acetylacetonate in tetrahydrofuran, Time= 0.166667h, Ambient temperature Fiandanese, V.; Marchese, G.; Martina, V.; Ronzini, L.; Tetrahedron Letters; vol. 25; nb. 42; (1984); p. 4805 - 4808 View in Reaxys With diethyl ether Gastambide; Annales de Chimie (Cachan, France); vol. <12>9; (1954); p. 257,305 View in Reaxys

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Rx-ID: 1673039 View in Reaxys 252/344 Yield

Conditions & References

80 %

in tetrahydrofuran, T= 0 °C Wattanasin, S.; Kathawala, F.G.; Tetrahedron Letters; vol. 25; nb. 8; (1984); p. 811 - 814 View in Reaxys

Rx-ID: 1984713 View in Reaxys 253/344 Yield

Conditions & References

3 % Chromat., 50 % Chromat.

With lithium dimethylcuprate in diethyl ether, Time= 1h, T= 0 °C , or (CH3)2CuLi*LiBr; variations of times, solvent, Mechanism, Product distribution Bertz, Steven H.; Dabbagh, Gary; Cook, James M.; Honkan, Vidya; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1739 - 1743 View in Reaxys

O–

O S

O N N+

Rx-ID: 2639006 View in Reaxys 254/344 Yield

Conditions & References With potassium carbonate in benzene, Time= 2h, T= 60 °C , Yield given Ohta, Shunsaku; Hayakawa, Satoshi; Nishimura, Kazuko; Okamoto, Masao; Tetrahedron Letters; vol. 25; nb. 30; (1984); p. 3251 - 3254 View in Reaxys

Rx-ID: 2852810 View in Reaxys 255/344

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Yield

Conditions & References

63 %

With N,N,N,N,-tetramethylethylenediamine, tert.-butyl lithium in hexane, T= -5 °C Trimitsis, G.; Beers, S.; Ridella, J.; Carlon, M.; Cullin, D.; et al.; Journal of the Chemical Society, Chemical Communications; nb. 16; (1984); p. 1088 - 1089 View in Reaxys

Rx-ID: 3805169 View in Reaxys 256/344 Yield

Conditions & References With hydrogenchloride, 1.) THF, ether, 4 h, reflux, Yield given. Multistep reaction Olah, George A.; Surya Prakash, G. K.; Arvanaghi, Massoud; Synthesis; nb. 3; (1984); p. 228 - 230 View in Reaxys

Zn(CN)2 O

Rx-ID: 18531175 View in Reaxys 257/344 Yield

Conditions & References Reaction Steps: 2 1: KH, NEt3 / tetrahydrofuran 2: 63 percent / tBuLi, TMEDA / hexane / -5 °C With N,N,N,N,-tetramethylethylenediamine, tert.-butyl lithium, potassium hydride, triethylamine in tetrahydrofuran, hexane Trimitsis, G.; Beers, S.; Ridella, J.; Carlon, M.; Cullin, D.; et al.; Journal of the Chemical Society, Chemical Communications; nb. 16; (1984); p. 1088 - 1089 View in Reaxys

O 5-benzoyl-O 1,O 2-isopropyliden-α-D-arabinofuranose Cl

Rx-ID: 21348514 View in Reaxys 258/344 Yield

Conditions & References Reaction Steps: 3 1: 81 percent / pyridine / Ambient temperature 2: 52 percent / NaH / dimethylformamide / 60 h 3: 80 percent / KOH / ethanol; H2O / Heating With potassium hydroxide, sodium hydride in pyridine, ethanol, water, N,N-dimethyl-formamide McEwen, William E.; Grossi, Anthony V.; MacDonald, Russell J.; Stamegna, Andrew P.; Journal of Organic Chemistry; vol. 45; nb. 7; (1980); p. 1301 - 1308

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View in Reaxys Reaction Steps: 2 1: pyridine / CHCl3 / 1 h / Ambient temperature 2: 84 percent / tetrahydrofuran / 1 h / 0 °C With pyridine in tetrahydrofuran, chloroform Nahm, Steven; Weinreb, Steven M.; Tetrahedron Letters; vol. 22; nb. 39; (1981); p. 3815 - 3818 View in Reaxys Reaction Steps: 2 1: pyridine / CHCl3 / 1 h / Ambient temperature 2: 91 percent / tetrahydrofuran / 1 h / 0 °C With pyridine in tetrahydrofuran, chloroform Nahm, Steven; Weinreb, Steven M.; Tetrahedron Letters; vol. 22; nb. 39; (1981); p. 3815 - 3818 View in Reaxys Reaction Steps: 2 1: triethylamine / petroleum ether / 0.75 h / 0 °C 2: 80 percent / tetrahydrofuran / 0 °C With triethylamine in tetrahydrofuran, Petroleum ether Wattanasin, S.; Kathawala, F.G.; Tetrahedron Letters; vol. 25; nb. 8; (1984); p. 811 - 814 View in Reaxys

Li (v1)

Rx-ID: 1778770 View in Reaxys 259/344 Yield 95 %

Conditions & References in diethyl ether, hexane, Time= 0.5h, T= -78 °C Kim, Sunggak; Lee, Jae In; Journal of Organic Chemistry; vol. 48; nb. 15; (1983); p. 2608 - 2610 View in Reaxys

Pd (v2)

2 P

Rx-ID: 2432693 View in Reaxys 260/344 Yield

Conditions & References With triphenylphosphine in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 6h, T= 65 °C

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Labadie, Jeff W.; Tueting, David; Stille, J. K.; Journal of Organic Chemistry; vol. 48; nb. 24; (1983); p. 4634 - 4642 View in Reaxys

O O

Rx-ID: 2707598 View in Reaxys 261/344 Yield 14 %, 36 %

Conditions & References With benzoylchlorobis(triphenylphosphine)palladium(II) in chloroform, Time= 18h, T= 65 °C Labadie, Jeff W.; Tueting, David; Stille, J. K.; Journal of Organic Chemistry; vol. 48; nb. 24; (1983); p. 4634 - 4642 View in Reaxys

Rx-ID: 2707793 View in Reaxys 262/344 Yield 85 %

Conditions & References With benzoylchlorobis(triphenylphosphine)palladium(II) in chloroform, Time= 40h, T= 65 °C Labadie, Jeff W.; Tueting, David; Stille, J. K.; Journal of Organic Chemistry; vol. 48; nb. 24; (1983); p. 4634 - 4642 View in Reaxys With benzylchlorobis(triphenylphosphine)pa.. in chloroform, T= 65 °C , other solvent; competition with Bu3SnPh; relative reaction rates of benzoyl chloride with organotins Labadie,J.W.; Stille,J.K.; Journal of the American Chemical Society; vol. 105; (1983); p. 6129 View in Reaxys

O O

Rx-ID: 2707931 View in Reaxys 263/344 Yield

Conditions & References With PdCl(COPh)(PPh3)2 in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 12h, T= 65 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Labadie, Jeff W.; Tueting, David; Stille, J. K.; Journal of Organic Chemistry; vol. 48; nb. 24; (1983); p. 4634 - 4642 View in Reaxys

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O H

Rx-ID: 2709363 View in Reaxys 264/344 Yield

Conditions & References

6 %, 19 %, 43 %

With benzoylchlorobis(triphenylphosphine)palladium(II) in chloroform, Time= 72h, T= 65 °C Labadie, Jeff W.; Tueting, David; Stille, J. K.; Journal of Organic Chemistry; vol. 48; nb. 24; (1983); p. 4634 - 4642 View in Reaxys

Rx-ID: 2937001 View in Reaxys 265/344 Yield

Conditions & References

6 % Chromat., 21 % Chromat.

in hexane, Time= 4h, Heating, Product distribution Richey, Herman G.; Erickson, Wayne F.; Journal of Organic Chemistry; vol. 48; nb. 23; (1983); p. 4349 - 4357 View in Reaxys

Li H 2N

NH 2

Rx-ID: 3551053 View in Reaxys 266/344 Yield

Conditions & References

15 % Chro- in hexane, Time= 4h, Heating, various temperatures, Product distribution mat., 2 % Richey, Herman G.; Erickson, Wayne F.; Journal of Organic Chemistry; vol. 48; nb. 23; (1983); p. 4349 - 4357 Chromat., 25 % Chro- View in Reaxys mat., 14 % Chromat., 3 % Chromat.

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O HO

Rx-ID: 3552599 View in Reaxys 267/344 Yield

Conditions & References With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride in tetrahydrofuran, Time= 24h, Ambient temperature, Yield given. Yields of byproduct given Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 24; nb. 34; (1983); p. 3677 - 3680 View in Reaxys

H 2N

Rx-ID: 3747227 View in Reaxys 268/344 Yield

Conditions & References

7 % Chromat., 13 % Chromat., 7 % Chromat., 12 % Chromat.

in hexane, Time= 4h, Heating, various temperatures, Product distribution

7 % Chromat., 13 % Chromat., 7 % Chromat., 12 % Chromat.

in hexane, 1.) ice bath, 2.) reflux, 4 h

Richey, Herman G.; Erickson, Wayne F.; Journal of Organic Chemistry; vol. 48; nb. 23; (1983); p. 4349 - 4357 View in Reaxys

N H

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N H

Rx-ID: 4263000 View in Reaxys 269/344 Yield

Conditions & References

0.7 g, 23 %, in pyridine, benzene, Time= 0.25h, Heating 63 % Cook, Lawrence S.; Venayak, Narinder D.; Wakefield, Basil J.; Journal of Chemical Research, Miniprint; nb. 8; (1983); p. 1813 - 1822 View in Reaxys

H N

N H

Rx-ID: 4266906 View in Reaxys 270/344 Yield 22 %, 44 %

Conditions & References With bromine in chloroform Cook, Lawrence S.; Venayak, Narinder D.; Wakefield, Basil J.; Journal of Chemical Research, Miniprint; nb. 8; (1983); p. 1813 - 1822 View in Reaxys

Rx-ID: 7159945 View in Reaxys 271/344 Yield

Conditions & References Deuchert,K. et al.; Chemische Berichte; vol. 112; (1979); p. 2045 - 2061 View in Reaxys Stork,G.; Maldonado,L.; Journal of the American Chemical Society; vol. 93; (1971); p. 5286 - 5287 View in Reaxys Posner,G.H. et al.; Journal of the American Chemical Society; vol. 94; (1972); p. 5106 - 5108 View in Reaxys Hegedus,L.S. et al.; Journal of the American Chemical Society; vol. 97; (1975); p. 5448 - 5452 View in Reaxys Compagnon,P.-L. et al.; Bulletin de la Societe Chimique de France; (1975); p. 779 - 782 View in Reaxys Pornet,J.; Miginiac,L.; Bulletin de la Societe Chimique de France; (1975); p. 841 - 845 View in Reaxys Pornet,J.; Miginiac,L.; Bulletin de la Societe Chimique de France; (1975); p. 1849 - 1854 View in Reaxys Kofron,W.G. et al.; Journal of Organic Chemistry; vol. 27; (1962); p. 2737 - 2741 View in Reaxys Gassman,P.G.; Richmond,G.D.; Journal of Organic Chemistry; vol. 31; (1966); p. 2355 - 2357

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View in Reaxys Negishi,E. et al.; Journal of Organic Chemistry; vol. 40; (1975); p. 1676 - 1677 View in Reaxys Pittman,C.U.; Hanes,R.M.; Journal of Organic Chemistry; vol. 42; (1977); p. 1194 - 1197 View in Reaxys Meyers,A.I. et al.; Journal of Organic Chemistry; vol. 43; (1978); p. 1372 - 1379 View in Reaxys Milstein,D.; Stille,J.K.; Journal of Organic Chemistry; vol. 44; (1979); p. 1613 - 1618 View in Reaxys Huenig,S.; Wehner,G.; Synthesis; (1975); p. 180 - 182 View in Reaxys Richey,H.G. et al.; Tetrahedron Letters; nb. 24; (1971); p. 2187 - 2190 View in Reaxys Ohno,A. et al.; Tetrahedron Letters; (1972); p. 4993 - 4996 View in Reaxys Gauthier,R. et al.; Journal of Organometallic Chemistry; vol. 140; (1977); p. 245 - 255 View in Reaxys Cuvigny; Normant; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 265; (1967); p. 245 View in Reaxys Cuvigny; Normant; Bulletin de la Societe Chimique de France; (1968); p. 4990 View in Reaxys Patent; Stetter et al.; US4014889; (1977) View in Reaxys Yamaguchi et al.; Chemistry and Industry (London, United Kingdom); (1972); p. 380 View in Reaxys Olah et al.; Synthesis; (1977); p. 677 View in Reaxys Araki et al.; Bulletin of the Chemical Society of Japan; vol. 47; (1974); p. 1777 View in Reaxys Abe et al.; Chemistry Letters; (1977); p. 645 View in Reaxys Schuikin et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1964); p. 694; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1964); p. 747 View in Reaxys Lee; Tetrahedron Letters; (1966); p. 5669,5672 View in Reaxys Berlin et al.; Journal of Organic Chemistry; vol. 30; (1965); p. 226,227 View in Reaxys Cookson; Farquharson; Tetrahedron Letters; (1979); p. 1255 View in Reaxys Hegedus et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 3040 View in Reaxys Saigo et al.; Chemistry Letters; (1976); p. 769,770 View in Reaxys Parham; Jones; Journal of Organic Chemistry; vol. 41; nb. 7; (1976); p. 1187,1189 View in Reaxys Parham; Sayed; Journal of Organic Chemistry; vol. 39; (1974); p. 2051 View in Reaxys Forrester et al.; Journal of the Chemical Society, Chemical Communications; (1976); p. 677 View in Reaxys Bergbreiter; Killough; Journal of Organic Chemistry; vol. 41; (1976); p. 2750 View in Reaxys Levine; Karten; Journal of Organic Chemistry; vol. 41; nb. 7; (1976); p. 1176,1178 View in Reaxys Ito et al.; Tetrahedron Letters; (1979); p. 2253,2254 View in Reaxys Denney; Kindsgrab; Journal of Organic Chemistry; vol. 28; (1963); p. 1133 View in Reaxys Turowa-Poljak et al.; Neftekhimiya; vol. 4; (1964); p. 603; ; p. 240 View in Reaxys

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Granito; Schultz; Journal of Organic Chemistry; vol. 28; (1963); p. 879 View in Reaxys Miyaura et al.; Tetrahedron Letters; (1977); p. 173 View in Reaxys House et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 3067,3072 View in Reaxys Cahiez et al.; Synthesis; (1977); p. 130 View in Reaxys Sawa et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 4183,4187 View in Reaxys Milstein; Stille; Journal of the American Chemical Society; vol. 100; (1978); p. 3636 View in Reaxys Barnhardt; McEwen; Journal of the American Chemical Society; vol. 89; (1967); p. 7009,7012 View in Reaxys Panasenko et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 26; (1977); p. 425; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 26; (1977); p. 470 View in Reaxys Turova-Polyak et al.; Moscow University Chemistry Bulletin (English Translation); vol. 22; nb. 3; (1967); p. 49; ; p. 68 View in Reaxys Patent; Goedecke AG; DE1593890; (1973); ; vol. 80; nb. 36840 View in Reaxys Tanaka; Tetrahedron Letters; (1979); p. 2601 View in Reaxys Kosugi et al.; Chemistry Letters; (1977); p. 1423 View in Reaxys Attanasi; Gasperoni; Gazzetta Chimica Italiana; vol. 108; (1978); p. 137 View in Reaxys Mukaiyama et al.; Bulletin of the Chemical Society of Japan; vol. 41; (1968); p. 1491 View in Reaxys Fauvarque et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 275; (1972); p. 511,513 View in Reaxys Emptoz et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 273; (1971); p. 1543 View in Reaxys Godet; Pereyre; Journal of Organometallic Chemistry; vol. 77; (1974); p. C1 View in Reaxys Kupin; Petrow; J. Gen. Chem. USSR (Engl. Transl.); vol. 31; (1961); p. 2958,2758; ; vol. 57; nb. 2125; (1962) View in Reaxys Bagnell et al.; Australian Journal of Chemistry; vol. 28; (1975); p. 821 View in Reaxys Iwanowa et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 3109,3148 View in Reaxys Morcillo et al.; Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica; vol. 60; (1964); p. 199,203 View in Reaxys Kurts et al.; Journal of Organometallic Chemistry; vol. 17; (1969); p. P21 View in Reaxys Michel et al.; Bulletin de la Societe Chimique de France; (1968); p. 4898 View in Reaxys Buchanan; Davis; Journal of the Chemical Society [Section] C: Organic; (1967); p. 1340 View in Reaxys Barltrop; Coyle; Journal of the American Chemical Society; vol. 90; (1968); p. 6584 View in Reaxys Piekarski et al.; Bulletin de la Societe Chimique de France; (1968); p. 4063 View in Reaxys These aldehydes and ketones are set forth for exemplification and are not to be construed as limiting the scope of this invention. benzaldehyde, ... acetophenone, 4-fluoroacetophenone,

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1-phenyl-2-propanone, 1-(4-imidazo-1-yl)phenylethanone, 1-phenyl-1-pentanone, diphenyl methanone (4-chlorophenyl)phenyl methanone, phenyl-2-pyridyl methanone, ... Patent; Schering Corporation; US4376769; (1983); (A) English View in Reaxys

phenylmagnesium halide O

Rx-ID: 7297732 View in Reaxys 272/344 Yield

Conditions & References With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride in tetrahydrofuran, Time= 72h, Ambient temperature, Yield given. Yields of byproduct given Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 24; nb. 34; (1983); p. 3677 - 3680 View in Reaxys

n-Butylmagnesium halide HO

Rx-ID: 7366640 View in Reaxys 273/344 Yield

Conditions & References in tetrahydrofuran, Time= 24h, Ambient temperature, Yield given. Yields of byproduct given Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 24; nb. 34; (1983); p. 3677 - 3680 View in Reaxys

Phenylmagnesium halide HO

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Rx-ID: 8539950 View in Reaxys 274/344 Yield

Phenylmagnesium halide O

Rx-ID: 10600617 View in Reaxys 275/344 Yield

Conditions & References in tetrahydrofuran, Time= 72h, Ambient temperature, Yield given. Yields of byproduct given Fiandanese, V.; Marchese, G.; Ronzini, L.; Tetrahedron Letters; vol. 24; nb. 34; (1983); p. 3677 - 3680 View in Reaxys

I N

Rx-ID: 1673084 View in Reaxys 276/344 Yield

Conditions & References Multistep reaction Marks, Maurice J.; Walborsky, Harry M.; Journal of Organic Chemistry; vol. 47; nb. 1; (1982); p. 52 - 56 View in Reaxys

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N H

Rx-ID: 1673085 View in Reaxys 277/344 Yield

Conditions & References 1.) hexane, RT, 30 min, 2.) -70 deg, 2.5 h, Multistep reaction Marks, Maurice J.; Walborsky, Harry M.; Journal of Organic Chemistry; vol. 47; nb. 1; (1982); p. 52 - 56 View in Reaxys

(v2)

Cu –

Li+

Rx-ID: 1984703 View in Reaxys 278/344 Yield

Conditions & References

65 %

Ambient temperature, overnight Johnson, Carl R.; Dhanoa, Daljit S.; Journal of the Chemical Society, Chemical Communications; nb. 6; (1982); p. 358 - 359 View in Reaxys

O HO O

HO HO

Rx-ID: 2155774 View in Reaxys 279/344 Yield

Conditions & References

0.01 mol, 0.19 mol, 0.20 mol, 0.18 mol

in n-heptane, T= 98 °C , Further byproducts given Lefort, D.; Nedelec, J. Y.; Tetrahedron; vol. 38; nb. 17; (1982); p. 2681 - 2686 View in Reaxys

O HO O O

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HO HO HO

Rx-ID: 2155775 View in Reaxys 280/344 Yield 0.01 mol, 0.19 mol, 0.20 mol, 0.18 mol, 0.01 mol

Conditions & References in n-heptane, T= 98 °C , Mechanism, Product distribution Lefort, D.; Nedelec, J. Y.; Tetrahedron; vol. 38; nb. 17; (1982); p. 2681 - 2686 View in Reaxys

Li+

Cu – (v2)

Rx-ID: 2712494 View in Reaxys 281/344 Yield 100 % Chromat.

Conditions & References in diethyl ether, T= 0 °C Bertz, Steven H.; Dabbagh, Gary; Villacorta, G. M.; Journal of the American Chemical Society; vol. 104; nb. 21; (1982); p. 5824 - 5826 View in Reaxys

Li O (v2)

N (v4)

Rx-ID: 2712495 View in Reaxys 282/344 Yield 98 % Chromat.

Li+ N Cl

Cu – (v2)

Rx-ID: 2712511 View in Reaxys 283/344 Yield 98 % Chromat.

Conditions & References in diethyl ether, T= 0 °C

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Bertz, Steven H.; Dabbagh, Gary; Villacorta, G. M.; Journal of the American Chemical Society; vol. 104; nb. 21; (1982); p. 5824 - 5826 View in Reaxys Li

(v2)

(v4)

Rx-ID: 2712546 View in Reaxys 284/344 Yield 97 % Chromat.

Li O

(v2)

(v3)

Rx-ID: 2712559 View in Reaxys 285/344 Yield 100 % Chromat.

Conditions & References in diethyl ether, T= -50 °C Bertz, Steven H.; Dabbagh, Gary; Villacorta, G. M.; Journal of the American Chemical Society; vol. 104; nb. 21; (1982); p. 5824 - 5826 View in Reaxys Li

(v2)

(v4)

Rx-ID: 2712608 View in Reaxys 286/344 Yield 100 % Chromat.

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O Cl

Li+

S O

Cu – (v2)

Rx-ID: 2714028 View in Reaxys 287/344 Yield

Conditions & References

90 %

With ammonium chloride in tetrahydrofuran, Time= 0.25h, T= -78 °C Johnson, Carl R.; Dhanoa, Daljit S.; Journal of the Chemical Society, Chemical Communications; nb. 6; (1982); p. 358 - 359 View in Reaxys

Li+

Cu –

S O

(v2)

Rx-ID: 2714035 View in Reaxys 288/344 Yield

Conditions & References

91 %

HO O P O O

Rx-ID: 3580082 View in Reaxys 289/344 Yield

Conditions & References With sodium hydroxide in ethanol, Time= 1h, Yield given Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys

H N

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Rx-ID: 4078667 View in Reaxys 290/344 Yield

Conditions & References

21 %, 42 %

Time= 0.5h, T= 300 °C Cook, Lawrence S.; Prudhoe, Gordon; Venayak, Narinder D.; Wakefield, Basil J.; Journal of Chemical Research, Miniprint; nb. 5; (1982); p. 1357 - 1367 View in Reaxys

21 %, 42 %

Time= 0.5h, T= 300 °C , other substrates, Product distribution, Mechanism Cook, Lawrence S.; Prudhoe, Gordon; Venayak, Narinder D.; Wakefield, Basil J.; Journal of Chemical Research, Miniprint; nb. 5; (1982); p. 1357 - 1367 View in Reaxys

Rx-ID: 18012943 View in Reaxys 291/344 Yield

Conditions & References Reaction Steps: 2 1: 67 percent / hexane / Ambient temperature 2: 0.5 h / 300 °C / other substrates in hexane Cook, Lawrence S.; Prudhoe, Gordon; Venayak, Narinder D.; Wakefield, Basil J.; Journal of Chemical Research, Miniprint; nb. 5; (1982); p. 1357 - 1367 View in Reaxys

Si O O P O

O O

Rx-ID: 19026239 View in Reaxys 292/344 Yield

Conditions & References Reaction Steps: 3 1: 1.) LDA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, hexane, -78 deg C, 0.8 h 2: p-toluenesulfonic acid / methanol; H2O / 0.67 h / Heating 3: 1 M NaOH / ethanol / 1 h

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With sodium hydroxide, toluene-4-sulfonic acid, lithium diisopropyl amide in methanol, ethanol, water Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys

oxygen O

Rx-ID: 19035990 View in Reaxys 293/344 Yield

Conditions & References Reaction Steps: 4 1: 91 percent / benzene / 6 h / Ambient temperature 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, hexane, -78 deg C, 0.8 h 3: p-toluenesulfonic acid / methanol; H2O / 0.67 h / Heating 4: 1 M NaOH / ethanol / 1 h With sodium hydroxide, toluene-4-sulfonic acid, lithium diisopropyl amide in methanol, ethanol, water, benzene Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys Reaction Steps: 4 1: 1.) Na 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, hexane, -78 deg C, 0.8 h 3: p-toluenesulfonic acid / methanol; H2O / 0.67 h / Heating 4: 1 M NaOH / ethanol / 1 h With sodium hydroxide, sodium, toluene-4-sulfonic acid, lithium diisopropyl amide in methanol, ethanol, water Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys

O P O

O O

Rx-ID: 19050831 View in Reaxys 294/344 Yield

Conditions & References Reaction Steps: 2 1: p-toluenesulfonic acid / methanol; H2O / 0.67 h / Heating 2: 1 M NaOH / ethanol / 1 h With sodium hydroxide, toluene-4-sulfonic acid in methanol, ethanol, water Sekine, Mitsuo; Nakajima, Masashi; Kume, Akiko; Hashizume, Akio; Hata, Tsujiaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 1; (1982); p. 224 - 238 View in Reaxys

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Si I

Rx-ID: 1781642 View in Reaxys 295/344 Yield

Conditions & References

35 %

With potassium fluoride in N,N,N,N,N,N-hexamethylphosphoric triamide Schinzer, Dieter; Heathcock, Clayton H.; Tetrahedron Letters; vol. 22; nb. 20; (1981); p. 1881 - 1884 View in Reaxys

Rx-ID: 1782059 View in Reaxys 296/344 Yield

Conditions & References

99 %

With nickel dichloride, zinc in N,N-dimethyl-formamide, Time= 5h, T= 50 °C Onaka, Makoto; Matsuoka, Yoshio; Mukaiyama, Teruaki; Chemistry Letters; (1981); p. 531 - 534 View in Reaxys

(v2)

Cu – Li+

Rx-ID: 1807646 View in Reaxys 297/344 Yield

Conditions & References

99 %

With nitrogen in diethyl ether, -78 deg C to r.t. Kim, Sunggak; Lee, Jae In; Chung, Bong Young; Journal of the Chemical Society, Chemical Communications; nb. 23; (1981); p. 1231 - 1232 View in Reaxys

O O

Rx-ID: 2038060 View in Reaxys 298/344 Yield 91 %

Conditions & References in tetrahydrofuran, Time= 1h, T= 0 °C

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Nahm, Steven; Weinreb, Steven M.; Tetrahedron Letters; vol. 22; nb. 39; (1981); p. 3815 - 3818 View in Reaxys

O Br

O N

Rx-ID: 2706485 View in Reaxys 299/344 Yield

Conditions & References With n-butyllithium, 1) 20 min, -100 deg C, 2) THF, 30 min, -100 deg C, Yield given. Multistep reaction. Yields of byproduct given Parham; Bradsher; Edgar; Journal of Organic Chemistry; vol. 46; nb. 6; (1981); p. 1057 - 1061 View in Reaxys

O S O

Rx-ID: 2827943 View in Reaxys 300/344 Yield

Conditions & References

0.34 %

With aluminium amalgam in tetrahydrofuran, water, Time= 0.25h Baylis, Christopher J.; Odle, Stanley W.; Tyman, John H. P.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 132 - 141 View in Reaxys

Rx-ID: 3878722 View in Reaxys 301/344 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 20h, T= 150 - 154 °C , other solvents, other temperatures, Product distribution Liu, Michael T. H.; Palmer, Glenn E.; Chishti, Najmul H.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 53 - 57 View in Reaxys

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Rx-ID: 3878726 View in Reaxys 302/344 Yield

Conditions & References With 3-chloro-benzenecarboperoxoic acid in diethyl ether, Time= 0.833333h, T= 20 °C , Irradiation, other solvents, Product distribution, Mechanism Liu, Michael T. H.; Palmer, Glenn E.; Chishti, Najmul H.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 53 - 57 View in Reaxys

O O

Rx-ID: 20582363 View in Reaxys 303/344 Yield

Conditions & References Reaction Steps: 2 1: 77 percent / sodium hydride / dimethylsulfoxide / 0.5 h 2: 0.34 percent / aluminium amalgam / tetrahydrofuran; H2O / 0.25 h With aluminium amalgam, sodium hydride in tetrahydrofuran, water, dimethyl sulfoxide Baylis, Christopher J.; Odle, Stanley W.; Tyman, John H. P.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 132 - 141 View in Reaxys

O O

Rx-ID: 1720598 View in Reaxys 304/344

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Yield

Conditions & References in trichlorofluoromethane, T= 21 °C , other temperatures; kinetics, Ea, ECL, ΔE, Ed; chemiluminiscent thermolysis of α-peroxylactones, Rate constant, Quantum yield, Thermodynamic data Turro, Nicolas J.; Chow, Ming-Fea; Journal of the American Chemical Society; vol. 102; nb. 15; (1980); p. 5058 - 5064 View in Reaxys

O N

N O

Rx-ID: 1842180 View in Reaxys 305/344 Yield

Conditions & References

34 %, 16 %, With ozone in tetrachloromethane, T= -20 °C , Yield given. Further byproducts given 13 % Ito, Yoshikatsu; Yokoya, Hiroaki; Umehara, Yasutoshi; Matsuura, Teruo; Bulletin of the Chemical Society of Japan; vol. 53; nb. 8; (1980); p. 2407 - 2408 View in Reaxys

O N

N O

Rx-ID: 1842181 View in Reaxys 306/344 Yield

Conditions & References

34 %, 16 %, With ozone in tetrachloromethane, T= -20 °C 13 %, 20 % Ito, Yoshikatsu; Yokoya, Hiroaki; Umehara, Yasutoshi; Matsuura, Teruo; Bulletin of the Chemical Society of Japan; vol. 53; nb. 8; (1980); p. 2407 - 2408 View in Reaxys 34 %, 16 %, With ozone in tetrachloromethane, T= -20 °C , Yield given. Further byproducts given 13 % Ito, Yoshikatsu; Yokoya, Hiroaki; Umehara, Yasutoshi; Matsuura, Teruo; Bulletin of the Chemical Society of Japan; vol. 53; nb. 8; (1980); p. 2407 - 2408

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View in Reaxys

H N N

Rx-ID: 2438087 View in Reaxys 307/344 Yield 100 %

Conditions & References With copper(II) sulfate in tetrahydrofuran, methanol, water, Time= 2.5h, Heating Attanasi, Orazio; Gasperoni, Simonetta; Carletti, Claudio; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 6; (1980); p. 1063 - 1066 View in Reaxys

Si O

Rx-ID: 2592654 View in Reaxys 308/344 Yield

Conditions & References With aqueous acid, Yield given Ager, David J.; Tetrahedron Letters; vol. 21; (1980); p. 4759 - 4762 View in Reaxys

N O

Rx-ID: 2604496 View in Reaxys 309/344 Yield 80 %

Conditions & References With potassium hydroxide in ethanol, water, Heating McEwen, William E.; Grossi, Anthony V.; MacDonald, Russell J.; Stamegna, Andrew P.; Journal of Organic Chemistry; vol. 45; nb. 7; (1980); p. 1301 - 1308 View in Reaxys

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H N

NH N

N H

Rx-ID: 2937004 View in Reaxys 310/344 Yield

Conditions & References

40 %, 4 %, in diethyl ether, Time= 16h, T= 20 °C , other solvents, temperature, time, reagents ratio, Product distribution 20 %, 13 %, Cook, Lawrence S.; Wakefield, Basil J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic 33 % Chemistry (1972-1999); (1980); p. 2392 - 2397 View in Reaxys

H N

NH N

N H

Rx-ID: 2937006 View in Reaxys 311/344 Yield

Conditions & References

29 %, 29 %, in diethyl ether, Time= 3h, T= -20 °C 10 %, 10 % Cook, Lawrence S.; Wakefield, Basil J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 2392 - 2397 View in Reaxys

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O S N

Rx-ID: 3267510 View in Reaxys 312/344 Yield

Conditions & References

90 %

With copper(II) sulfate in tetrahydrofuran, methanol, water, Time= 5h, Heating Attanasi, Orazio; Gasperoni, Simonetta; Carletti, Claudio; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 6; (1980); p. 1063 - 1066 View in Reaxys

N N

O O

Rx-ID: 3662913 View in Reaxys 313/344 Yield 55 % Spectr.

Conditions & References With oxygen, 5,15,10,20-tetraphenylporphyrin in trichlorofluoromethane, T= -78 °C , Irradiation Ito, Yoshikatsu; Yokoya, Hiroaki; Kyono, Kazuaki; Yamamura, Soichiro; Yamada, Yutaka; Matsuura, Teruo; Journal of the Chemical Society, Chemical Communications; nb. 19; (1980); p. 898 - 900 View in Reaxys

O O

Rx-ID: 3664426 View in Reaxys 314/344 Yield

Conditions & References in trichlorofluoromethane, T= -30 °C , other objects of study: activation energy, triplet-excitation yield (3α), Rate constant, Thermodynamic data Ito, Yoshikatsu; Yokoya, Hiroaki; Kyono, Kazuaki; Yamamura, Soichiro; Yamada, Yutaka; Matsuura, Teruo; Journal of the Chemical Society, Chemical Communications; nb. 19; (1980); p. 898 - 900 View in Reaxys

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N O

Rx-ID: 21367385 View in Reaxys 315/344 Yield

Conditions & References Reaction Steps: 2 1: 52 percent / NaH / dimethylformamide / 60 h 2: 80 percent / KOH / ethanol; H2O / Heating With potassium hydroxide, sodium hydride in ethanol, water, N,N-dimethyl-formamide McEwen, William E.; Grossi, Anthony V.; MacDonald, Russell J.; Stamegna, Andrew P.; Journal of Organic Chemistry; vol. 45; nb. 7; (1980); p. 1301 - 1308 View in Reaxys

O Br

Rx-ID: 907666 View in Reaxys 316/344 Yield

Conditions & References in N,N,N,N,N,N-hexamethylphosphoric triamide Huet,F. et al.; Tetrahedron; vol. 29; (1973); p. 479 - 485 View in Reaxys

Br Mg

Rx-ID: 1259666 View in Reaxys 317/344 Yield

Conditions & References in N,N,N,N,N,N-hexamethylphosphoric triamide Huet,F. et al.; Tetrahedron; vol. 29; (1973); p. 479 - 485 View in Reaxys

O S

Rx-ID: 589852 View in Reaxys 318/344

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Yield

Conditions & References With methanol, cobalt Badger et al.; Journal of the Chemical Society; (1959); p. 440,442 View in Reaxys With ethanol, nickel Blicke; Sheets; Journal of the American Chemical Society; vol. 71; (1949); p. 4010 View in Reaxys

Raney cobalt S

O O

Rx-ID: 5480483 View in Reaxys 319/344 Yield

Conditions & References Badger; Sasse; Journal of the Chemical Society; (1957); p. 3862,3867 View in Reaxys Blicke; Sheets; Journal of the American Chemical Society; vol. 71; (1949); p. 4010 View in Reaxys Badger et al.; Journal of the Chemical Society; (1959); p. 440,442 View in Reaxys

Raney nickel S

O O

Rx-ID: 5480484 View in Reaxys 320/344 Yield

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Br Mg N

Rx-ID: 762971 View in Reaxys 321/344 Yield

Conditions & References With diethyl ether Potschinok; Pompa; ; vol. 16; nb. 8; (1957); p. 129,131; ; (1959); p. 11289 View in Reaxys

Rx-ID: 225190 View in Reaxys 322/344 Yield

Conditions & References With boron trifluoride, benzene Olah; Kuhn; Chemische Berichte; vol. 89; (1956); p. 864 View in Reaxys

Cl N O

Rx-ID: 76998 View in Reaxys 323/344 Yield

Conditions & References With pyridine Hebbelynck; Martin; Bulletin des Societes Chimiques Belges; vol. 60; (1951); p. 54,65 View in Reaxys

Br–

+Mg

Rx-ID: 220486 View in Reaxys 324/344 Yield

Conditions & References With diethyl ether, Eintragen des Reaktionsgemisches in Eis und wss. HCl und Kochen der erhaltenen wss. Loesung Hauser; Humphlett; Weiss; Journal of the American Chemical Society; vol. 70; (1948); p. 426 View in Reaxys

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Shriner; Turner; Journal of the American Chemical Society; vol. 52; (1930); p. 1267 View in Reaxys

Rx-ID: 266933 View in Reaxys 325/344 Yield

Conditions & References McElvain; Kent; Stevens; Journal of the American Chemical Society; vol. 68; (1946); p. 1922,1924 View in Reaxys

Rx-ID: 510022 View in Reaxys 326/344 Yield

Conditions & References With sodium hydroxide McElvain; Kent; Stevens; Journal of the American Chemical Society; vol. 68; (1946); p. 1922,1924 View in Reaxys

Rx-ID: 847689 View in Reaxys 327/344 Yield

Conditions & References With aluminium trichloride Williams; Dickert; Krynitsky; Journal of the American Chemical Society; vol. 63; (1941); p. 2511 View in Reaxys

Al Cl

Rx-ID: 7061727 View in Reaxys 328/344

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Yield

Conditions & References zuletzt auf dem Wasserbad Williams; Dickert; Krynitsky; Journal of the American Chemical Society; vol. 63; (1941); p. 2511 View in Reaxys

Rx-ID: 22207682 View in Reaxys 329/344 Yield

Conditions & References Reaction Steps: 2 2: AlCl3 With aluminium trichloride Williams; Dickert; Krynitsky; Journal of the American Chemical Society; vol. 63; (1941); p. 2511 View in Reaxys

H N N

Rx-ID: 597659 View in Reaxys 330/344 Yield

Conditions & References With diethyl ether, Schuetteln des Reaktionsprodukts mit verd. wss. Schwefelsaeure Adamson; Kenner; Journal of the Chemical Society; (1939); p. 181,185 View in Reaxys H 2N

Mg O

compound C32H53Cl2N9O2(?) NH 2

Rx-ID: 8272782 View in Reaxys 331/344 Yield

Conditions & References Erwaermen des vom Aether befreiten Reaktionsgemisches in Benzol auf dem Dampfbad und anschliessend Behandeln mit Eis und NH4Cl

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Biquard; Bulletin de la Societe Chimique de France; vol. <5>5; (1938); p. 209,211 View in Reaxys O O H

aqueous Ba(OH)2

HO O O

Rx-ID: 8258731 View in Reaxys 332/344 Yield

Conditions & References Lutz; Stuart; Journal of the American Chemical Society; vol. 58; (1936); p. 1885,1887, 1889; Journal of the American Chemical Society; vol. 61; (1939); p. 1465,1467, 1469 View in Reaxys

Rx-ID: 455672 View in Reaxys 333/344 Yield

Conditions & References T= 300 °C Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys T= 300 °C Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys

oxygen

HO HO

Rx-ID: 7447481 View in Reaxys 334/344 Yield

Conditions & References T= 130 °C

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Dupont; Chavanne; Bulletin des Societes Chimiques Belges; vol. 42; (1933); p. 537 View in Reaxys

Rx-ID: 22124508 View in Reaxys 335/344 Yield

Conditions & References Reaction Steps: 2 1: KOH 2: 300 °C With potassium hydroxide Lauer; Spielman; Journal of the American Chemical Society; vol. 55; (1933); p. 4923,4927 View in Reaxys

O O

platinum

Rx-ID: 7981314 View in Reaxys 336/344 Yield

Conditions & References und Behandeln des erhaltenen Gemisches mit wss.NaOH dann Erwaermen des Reaktionsprodukts mit K2Cr2O7 und wss.H2SO4.Hydrogenation Roll; Adams; Journal of the American Chemical Society; vol. 53; (1931); p. 3469,3474 View in Reaxys

CrO3 O H

Rx-ID: 7981312 View in Reaxys 337/344 Yield

Conditions & References Liepins; ; vol. 1; (1930); p. 145,208; Chem. Zentralbl.; vol. 102; nb. I; (1931); p. 2619 View in Reaxys

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CrO3 O

Rx-ID: 7981313 View in Reaxys 338/344 Yield

Conditions & References Liepins; ; vol. 1; (1930); p. 145,208; Chem. Zentralbl.; vol. 102; nb. I; (1931); p. 2619 View in Reaxys

2-amino-1-phenyl-pentanol-(1) O

Rx-ID: 7159948 View in Reaxys 339/344 Yield

Conditions & References With cis-nitrous acid Tiffeneau; Levy; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 183; (1926); p. 970 View in Reaxys

O N

NH 2

Rx-ID: 7981311 View in Reaxys 340/344 Yield

Conditions & References Tiffeneau; Levy; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 183; (1926); p. 970 View in Reaxys

Rx-ID: 632780 View in Reaxys 341/344 Yield

Conditions & References With sodium amide, xylene Haller; Bauer; Annales de Chimie (Cachan, France); vol. <8> 28; (1913); p. 407; Annales de Chimie (Cachan, France); vol. <9> 1; (1914); p. 27 View in Reaxys

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Rx-ID: 758047 View in Reaxys 342/344 Yield

Conditions & References T= 430 - 490 °C , beim Leiten ueberFe2O3 Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 157; (1913); p. 221; Bulletin de la Societe Chimique de France; vol. <4> 15; (1914); p. 325 View in Reaxys

α-benzoyl-n-valeric acid ethyl ester O

Rx-ID: 7159946 View in Reaxys 343/344 Yield

Conditions & References With potassium hydroxide Perkin; Calman; Journal of the Chemical Society; vol. 49; (1886); p. 160 View in Reaxys

diluted alcoholic potash O

Rx-ID: 7542770 View in Reaxys 344/344 Yield

Conditions & References Perkin; Calman; Journal of the Chemical Society; vol. 49; (1886); p. 160 View in Reaxys

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