2-Phenylcyclohexanone [C12H14O] by Asch

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1. Query

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Date

139 reactions in Reaxys

2018-01-23 08h:44m:11s (EST)

139 reactions in Reaxys

2018-01-23 08h:44m:26s (EST)

Search as: As drawn 2. Query

(1. Query) AND itemno in (1)

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Rx-ID: 363123 View in Reaxys 1/139 Yield

Conditions & References

91 %

With boron trifluoride diethyl etherate in dichloromethane, Time= 1h, T= 20 °C , Inert atmosphere, regioselective reaction Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814 View in Reaxys With sulfuric acid Boeeseken; Chemische Berichte; vol. 56; (1923); p. 2410; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 687 View in Reaxys Le Brazidec; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 159; (1914); p. 775,776; Bulletin de la Societe Chimique de France; vol. <4> 17; (1915); p. 108,109 View in Reaxys

OH racemate

Rx-ID: 2199019 View in Reaxys 2/139 Yield 99 %

Conditions & References With peracetic acid, 2,4-dimethylpentane-2,4-diol cyclic chromate in tetrachloromethane, dichloromethane, Time= 0.5h, T= 0 °C Corey, E. J.; Barrette, Ernie-Paul; Magriotis, Plato A.; Tetrahedron Letters; vol. 26; nb. 48; (1985); p. 5855 - 5858 View in Reaxys

99 %

With sodium hypochlorite, 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, Time= 0.333333h, T= 0 °C , Inert atmosphere, Reagent/catalyst Sasano, Yusuke; Nishiyama, Tomohiro; Tomizawa, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Heterocycles; vol. 87; nb. 10; (2013); p. 2109 - 2118 View in Reaxys

98 %

With water, Dess-Martin periodane in dichloromethane, Time= 1.2h Meyer, Stephanie D.; Schreiber, Stuart L.; Journal of Organic Chemistry; vol. 59; nb. 24; (1994); p. 7549 - 7552 View in Reaxys

97 %

Stage 1: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate, T= 80 °C Stage 2: With sodium carbonate, sodium thiosulfate in water Younai, Ashkaan; Fettinger, James C.; Shaw, Jared T.; Tetrahedron; vol. 68; nb. 22; (2012); p. 4320 - 4327 View in Reaxys

96 %

With pyridine, chromium(VI) oxide in dichloromethane Barentsen, Helma M.; Talman, Edger G.; Piet, Dennis P.; Cornelisse, Jan; Tetrahedron; vol. 51; nb. 27; (1995); p. 7469 - 7494 View in Reaxys

78 %

With Dess-Martin periodane in dichloromethane, water, Time= 0.5h Wappes, Ethan A.; Nakafuku, Kohki M.; Nagib, David A.; Journal of the American Chemical Society; vol. 139; nb. 30; (2017); p. 10204 - 10207

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View in Reaxys With chromium(VI) oxide in acetic acid Zhou, Hui; Moberg, Christina; Journal of the American Chemical Society; vol. 134; nb. 38; (2012); p. 15992 15999 View in Reaxys

Cl Mg

Rx-ID: 33715201 View in Reaxys 3/139 Yield

Conditions & References Reaction Steps: 2 1.1: tetrahydrofuran / 2.67 h / 0 - 20 °C / Inert atmosphere 1.2: 0 °C 1.3: 16 h / 125 °C 2.1: dimethylsulfide; dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 2.2: 0 °C 2.3: 20 °C / Inert atmosphere With dimethylsulfide, dimethylsulfide borane complex in tetrahydrofuran Reichle, Markus A.; Breit, Bernhard; Angewandte Chemie - International Edition; vol. 51; nb. 23; (2012); p. 5730 5734 View in Reaxys Reaction Steps: 2 1: copper(l) chloride / tetrahydrofuran / 0 °C / Inert atmosphere 2: chromium(VI) oxide / acetic acid With chromium(VI) oxide, copper(l) chloride in tetrahydrofuran, acetic acid Zhou, Hui; Moberg, Christina; Journal of the American Chemical Society; vol. 134; nb. 38; (2012); p. 15992 15999 View in Reaxys Reaction Steps: 2 1.1: tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 20 °C / Inert atmosphere With boron trifluoride diethyl etherate in tetrahydrofuran, dichloromethane Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814 View in Reaxys Reaction Steps: 2 1.1: tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 20 °C / Inert atmosphere With boron trifluoride diethyl etherate in tetrahydrofuran, dichloromethane Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814 View in Reaxys

O O

Rx-ID: 34117106 View in Reaxys 4/139

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Yield

Conditions & References Reaction Steps: 2 1: copper(l) chloride / tetrahydrofuran / 0 °C / Inert atmosphere 2: chromium(VI) oxide / acetic acid With chromium(VI) oxide, copper(l) chloride in tetrahydrofuran, acetic acid Zhou, Hui; Moberg, Christina; Journal of the American Chemical Society; vol. 134; nb. 38; (2012); p. 15992 15999 View in Reaxys Reaction Steps: 2 1.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 20 °C 1.2: 8 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 10 h / 20 °C With copper(l) iodide, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, dimethyl sulfoxide Kano, Taichi; Hayashi, Yumi; Maruoka, Keiji; Journal of the American Chemical Society; vol. 135; nb. 19; (2013); p. 7134 - 7137 View in Reaxys Reaction Steps: 2 1: copper(l) iodide / diethyl ether / 7.5 h / 0 - 20 °C 2: Dess-Martin periodane / dichloromethane; water / 0.5 h With copper(l) iodide, Dess-Martin periodane in diethyl ether, dichloromethane, water Wappes, Ethan A.; Nakafuku, Kohki M.; Nagib, David A.; Journal of the American Chemical Society; vol. 139; nb. 30; (2017); p. 10204 - 10207 View in Reaxys

Br Mg

Rx-ID: 35527893 View in Reaxys 5/139 Yield

Conditions & References Reaction Steps: 2 1.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 20 °C 1.2: 8 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 10 h / 20 °C With copper(l) iodide, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, dimethyl sulfoxide Kano, Taichi; Hayashi, Yumi; Maruoka, Keiji; Journal of the American Chemical Society; vol. 135; nb. 19; (2013); p. 7134 - 7137 View in Reaxys Reaction Steps: 2 1: copper(l) iodide / diethyl ether / 7.5 h / 0 - 20 °C 2: Dess-Martin periodane / dichloromethane; water / 0.5 h With copper(l) iodide, Dess-Martin periodane in diethyl ether, dichloromethane, water Wappes, Ethan A.; Nakafuku, Kohki M.; Nagib, David A.; Journal of the American Chemical Society; vol. 139; nb. 30; (2017); p. 10204 - 10207 View in Reaxys

O HO

Rx-ID: 45848141 View in Reaxys 6/139

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Yield

Conditions & References Reaction Steps: 2 1.1: tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 20 °C / Inert atmosphere With boron trifluoride diethyl etherate in tetrahydrofuran, dichloromethane Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814 View in Reaxys

O HO

Rx-ID: 45848142 View in Reaxys 7/139 Yield

Conditions & References Reaction Steps: 2 1.1: tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 20 °C / Inert atmosphere With boron trifluoride diethyl etherate in tetrahydrofuran, dichloromethane Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814 View in Reaxys

Rx-ID: 45848156 View in Reaxys 8/139 Yield

Conditions & References

20 %, 65 %

With boron trifluoride diethyl etherate in dichloromethane, Time= 2h, T= 20 °C , Inert atmosphere, regioselective reaction Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814 View in Reaxys

Rx-ID: 308873 View in Reaxys 9/139 Yield 88 %

Conditions & References With pivaloyl chloride, dimethyl sulfoxide, triethylamine in dichloromethane, Time= 1h, T= -78 - 20 °C Dubey, Abhishek; Kandula, Subba Rao V.; Kumar, Pradeep; Synthetic Communications; vol. 38; nb. 5; (2008); p. 746 - 753 View in Reaxys With chromic acid, acetic acid v. Braun; Gruber; Kirschbaum; Chemische Berichte; vol. 55; (1922); p. 3672 View in Reaxys

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With 1,10-Phenanthroline, oxygen, potassium carbonate, copper(l) chloride in benzene, Time= 2h, Heating, Yield given Jallabert, C.; Riviere, H.; Tetrahedron; vol. 36; nb. 82; (1980); p. 1191 - 1194 View in Reaxys With chromium(VI) oxide, sulfuric acid in acetone Nishiyama; Park; Itoh; Tetrahedron Asymmetry; vol. 3; nb. 8; (1992); p. 1029 - 1034 View in Reaxys With Dess-Martin periodane in dichloromethane, T= 20 °C Pinard, Emmanuel; Ceccarelli, Simona M.; Stalder, Henri; Alberati, Daniela; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 2; (2006); p. 349 - 353 View in Reaxys With silica gel, pyridinium chlorochromate in dichloromethane, Time= 14h, T= 20 °C , Inert atmosphere Poe, Sarah L.; Morken, James P.; Angewandte Chemie - International Edition; vol. 50; nb. 18; (2011); p. 4189 4192 View in Reaxys With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 10h, T= 20 °C Kano, Taichi; Hayashi, Yumi; Maruoka, Keiji; Journal of the American Chemical Society; vol. 135; nb. 19; (2013); p. 7134 - 7137 View in Reaxys 3 : Embodiment 3 The 1.76g2-phenyl-cyclohexanol, 0.05mol percent (relative to the substrate 2-phenyl-cyclohexanol) aza jin'gang alkane nitroxyl radical (II), 0.5mol percent (relative to the substrate 2-phenyl-cyclohexanol) trichloro oxygen vanadium, 5 ml acetonitrile is added to the reactor, the charge air pressure is 0.5 MPa, in the 80 °C running 20h then cooled to room temperature. Sampling by the use of gas chromatography analysis, 2-phenyl-cyclohexanol conversion 99.7percent, 2-phenyl-cyclohexanone selectivity of 99.8percent. With 1-methyl-2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl, oxovanadium(IV) sulfate, oxygen in acetonitrile, Time= 20h, T= 80 °C , p= 3750.38Torr Patent; Dalian University of Technology; Du, zhongtian; Tang, yangyang; Sun, xiaowan; (5 pag.); CN105541526; (2016); (A) Chinese View in Reaxys

Rx-ID: 6524247 View in Reaxys 10/139 Yield 99 %

Conditions & References General procedure: In the reaction path shown in the above equation,Oxidation reaction was carried out using l-menthol as a substrate.Well, l-mento(156 mg, 1.00 mmol),4-oxa-5-azahomoadamantane(1.53 mg, 10 [mu] mol),Hydrogen carbonate sodium(NaHCO3, 167.7, 2.00 mmol)Was dissolved in dichloromethane(CH2Cl2, 5 mL) and cooled with ice(TCCA, 122.1 mg, 0.50 m) was added to the reaction solution.Mol) were added and reacted at the same temperature. With trichloroisocyanuric acid, 4-oxa-5-azahomoadamantane, sodium hydrogencarbonate in dichloromethane, Time= 1.5h, T= 0 °C Patent; Tohoku University; Iwabuchi, Yoshiharu; Sasano, Yusuke; Murakami, Keiichi; (21 pag.); JP6054900; (2016); (B2) Japanese View in Reaxys Herstellung von 2-Phenyl-<2-14 C>cyclohexanon

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Schaeffer; Collins; Journal of the American Chemical Society; vol. 72; (1956); p. 124,130 View in Reaxys Rosenmund,P. et al.; Chemische Berichte; vol. 103; (1970); p. 496 - 509 View in Reaxys Kuehne,M.E.; Journal of the American Chemical Society; vol. 84; (1962); p. 837 - 847 View in Reaxys House,H.O. et al.; Journal of the American Chemical Society; vol. 94; (1972); p. 8471 - 8475 View in Reaxys Crouzet,J.; Giral,L.; Bulletin de la Societe Chimique de France; (1968); p. 4842 - 4850 View in Reaxys Leyendecker,F. et al.; Bulletin de la Societe Chimique de France; (1970); p. 549 - 555 View in Reaxys Caubere,P. et al.; Bulletin de la Societe Chimique de France; (1971); p. 302 - 307 View in Reaxys Shono,T. et al.; Chemistry Letters; (1976); p. 1319 - 1322 View in Reaxys Woods,F. et al.; Journal of Organic Chemistry; vol. 26; (1961); p. 309 - 312 View in Reaxys Tomboulian,P.; Journal of Organic Chemistry; vol. 26; (1961); p. 2652 - 2656 View in Reaxys Sundberg,R.J.; Bukowick,P.A.; Journal of Organic Chemistry; vol. 33; nb. 11; (1968); p. 4098 - 4102 View in Reaxys House,H.O. et al.; Journal of Organic Chemistry; vol. 43; (1978); p. 700 - 710 View in Reaxys Birch et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1973); p. 1882,1891 View in Reaxys Battistini et al.; Gazzetta Chimica Italiana; vol. 107; (1977); p. 153 View in Reaxys Mandrou et al.; Bulletin de la Societe Chimique de France; (1962); p. 1551 View in Reaxys Salesskaja; Nezezkaja; Journal of Organic Chemistry USSR (English Translation); vol. 5; (1969); p. 1563; Zhurnal Organicheskoi Khimii; vol. 5; (1969); p. 1605 View in Reaxys Heaney; Ley; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1974); p. 2693 View in Reaxys Farberov et al.; Journal of Organic Chemistry USSR (English Translation); vol. 10; (1974); p. 48,51; Zhurnal Organicheskoi Khimii; vol. 10; (1974); p. 50 View in Reaxys Sacks; Fuchs; Synthesis; (1976); p. 456 View in Reaxys Caubere et al.; Tetrahedron; vol. 29; (1973); p. 1857,1858,1860,1861 View in Reaxys Sawaki; Ogata; Journal of the American Chemical Society; vol. 97; (1975); p. 6983,6984-6989 View in Reaxys Villieras et al.; Synthesis; (1979); p. 968 View in Reaxys Guyon; Villa; Bulletin de la Societe Chimique de France; (1975); p. 2593,2594, 2598 View in Reaxys Kern et al.; Makromolekulare Chemie; vol. 42; (1960); p. 177,186 View in Reaxys Prayer et al.; Australian Journal of Chemistry; vol. 31; (1978); p. 1989,1991, 1997 View in Reaxys Sacks; Fuchs; Journal of the American Chemical Society; vol. 97; (1975); p. 7373 View in Reaxys Yoshitake; Yakugaku Zasshi; vol. 83; (1963); p. 532,540; ; vol. 59; nb. 7407; (1963) View in Reaxys Botteron; Wood; Journal of Organic Chemistry; vol. 30; (1965); p. 3871,3874 View in Reaxys Dimmock; Turner; Canadian Journal of Pharmaceutical Sciences; vol. 9; (1974); p. 33,34-35

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View in Reaxys Crouzet et al.; Bulletin de la Societe Chimique de France; (1967); p. 3722 View in Reaxys Laurent; Villa; Bulletin de la Societe Chimique de France; (1969); p. 249 View in Reaxys Sisti; Journal of Organic Chemistry; vol. 33; (1968); p. 453 View in Reaxys 189 : 2-phenylcyclohexanone, oxime STR195 EXAMPLE 189 2-phenylcyclohexanone, oxime STR195 A sample of 2-phenylcyclohexanone (Aldrich, 10.4 g, 60 mmol) was converted to the title compound by the method of EXAMPLE 24 using 7.2 g (104 mmol) of hydroxylamine hydrochloride and 8.4 g (102 mmol) of NaOAc in a mixture of 75 mL of EtOH and 75 mL of water. The procedure produced 11.0 g (97percent) of the title material as a white solid. Patent; G. D. Searle and Co.; US5854234; (1998); (A1) English View in Reaxys Patent; G.D. Searle and Co.; US6046211; (2000); (A1) English View in Reaxys Exemplary of such ketones, the following are representative: ... 2-Methylcyclohexanone; 2-Methylcyclopentanone; 2,5-Dimethylcyclopentanone; 2,6-Dimethylcyclohexanone; and 2-Phenylcyclohexanone. Patent; Rhone-Poulenc Chimie; US4983767; (1991); (A1) English View in Reaxys

Rx-ID: 29766610 View in Reaxys 11/139 Yield 100 %

Conditions & References With (S)-2′-(diphenylphosphino)-1,1′-binaphthyl-2-ol, isopropyl alcohol, scandium tris(trifluoromethanesulfonate) in dichloromethane, Time= 12h, T= 20 °C , Inert atmosphere Cheon, Cheol Hong; Imahori, Tatsushi; Yamamoto, Hisashi; Chemical Communications; vol. 46; nb. 37; (2010); p. 6980 - 6982 View in Reaxys With silver tetrafluoroborate, (R)-BINAP(AuCl)2 in dichloromethane, 2,2,2-trifluoroethanol, Time= 12h, T= 20 °C , Inert atmosphere Cheon, Cheol Hong; Kanno, Osamu; Toste, F. Dean; Journal of the American Chemical Society; vol. 133; nb. 34; (2011); p. 13248 - 13251 View in Reaxys

84 %Spectr.

With 7-bromonaphthalen-2-ol, phenol in (2)H8-toluene, Time= 20h, UV-irradiation, Reagent/catalyst Das, Anjan; Banerjee, Tanmay; Hanson, Kenneth; Chemical Communications; vol. 52; nb. 7; (2016); p. 1350 1353 View in Reaxys

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Rx-ID: 33715210 View in Reaxys 12/139 Yield

Rx-ID: 41969643 View in Reaxys 13/139 Yield

Conditions & References

76 %Spectr.

With 7-bromonaphthalen-2-ol, phenol in (2)H8-toluene, Time= 20h, UV-irradiation Das, Anjan; Banerjee, Tanmay; Hanson, Kenneth; Chemical Communications; vol. 52; nb. 7; (2016); p. 1350 1353 View in Reaxys

Rx-ID: 41969644 View in Reaxys 14/139 Yield 68 %Spectr.

Conditions & References With 7-bromonaphthalen-2-ol, phenol in (2)H8-toluene, Time= 20h, UV-irradiation Das, Anjan; Banerjee, Tanmay; Hanson, Kenneth; Chemical Communications; vol. 52; nb. 7; (2016); p. 1350 1353 View in Reaxys

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Rx-ID: 41969645 View in Reaxys 15/139 Yield

Conditions & References

64 %Spectr.

Yield

Conditions & References With hydrogen, Time= 10h, T= 200 °C , p= 9000.9Torr , Reagent/catalyst Dong, Peng; Lu, Guo-Ping; Cai, Chun; New Journal of Chemistry; vol. 40; nb. 2; (2016); p. 1605 - 1609 View in Reaxys

Rx-ID: 42973317 View in Reaxys 17/139 Yield

Conditions & References Reaction Steps: 3 1.1: n-butyllithium / hexane / 2 h / -78 - 23 °C 2.1: benzene / 1 h / -78 - 23 °C 3.1: tetrahydrofuran / 44 h / 23 °C 3.2: 19 h / Reflux With n-butyllithium in tetrahydrofuran, hexane, benzene Jacobs, Brian P.; Wolczanski, Peter T.; Lobkovsky, Emil B.; Inorganic Chemistry; vol. 55; nb. 9; (2016); p. 4223 4232 View in Reaxys

–

N Li+ O

Rx-ID: 42973329 View in Reaxys 18/139 Yield

Conditions & References Reaction Steps: 2 1.1: benzene / 1 h / -78 - 23 °C 2.1: tetrahydrofuran / 44 h / 23 °C 2.2: 19 h / Reflux in tetrahydrofuran, benzene Jacobs, Brian P.; Wolczanski, Peter T.; Lobkovsky, Emil B.; Inorganic Chemistry; vol. 55; nb. 9; (2016); p. 4223 4232 View in Reaxys

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(v3) – N

(v3)

N–

Fe 2+ (v4)

(v3)

Rx-ID: 42973347 View in Reaxys 19/139 Yield

Conditions & References Stage 1: in tetrahydrofuran, Time= 44h, T= 23 °C Stage 2: in tetrahydrofuran, water, Time= 19h, Reflux Jacobs, Brian P.; Wolczanski, Peter T.; Lobkovsky, Emil B.; Inorganic Chemistry; vol. 55; nb. 9; (2016); p. 4223 4232 View in Reaxys

Rx-ID: 43555662 View in Reaxys 20/139 Yield 27 %, 37 %

Conditions & References With chloropyridinecobaloxime(III), water, 9-(2-mesityl)-10-methylacridinium perchlorate in acetonitrile, Time= 24h, T= 20 °C , Inert atmosphere, Schlenk technique, Irradiation, Wacker Oxidation Zhang, Guoting; Hu, Xia; Chiang, Chien-Wei; Yi, Hong; Pei, Pengkun; Singh, Atul K.; Lei, Aiwen; Journal of the American Chemical Society; vol. 138; nb. 37; (2016); p. 12037 - 12040 View in Reaxys

Rx-ID: 279574 View in Reaxys 21/139 Yield 84 %

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

70 %

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

66 %

Stage 1: With dimethylsulfide, dimethylsulfide borane complex in tetrahydrofuran, Time= 3h, T= 0 - 20 °C , Inert atmosphere Stage 2: With water, sodium hydroxide in tetrahydrofuran, T= 0 °C Stage 3: With pyridinium chlorochromate in dichloromethane, T= 20 °C , Inert atmosphere Reichle, Markus A.; Breit, Bernhard; Angewandte Chemie - International Edition; vol. 51; nb. 23; (2012); p. 5730 5734

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View in Reaxys With formic acid, dihydrogen peroxide, T= 40 °C Goldschmidt; Veer; Recueil des Travaux Chimiques des Pays-Bas; vol. 67; (1948); p. 489,506 View in Reaxys With Perbenzoic acid Filler et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 658,661 View in Reaxys With borane-THF, 4 A molecular sieve, pyridinium chlorochromate, 1.) THF, 2 deg C, 1 h, 2.) CH2Cl2, reflux, 3 h, Yield given. Multistep reaction Parish, Edward J.; Parish, Sarawanee; Honda, Hiroshi; Synthetic Communications; vol. 20; nb. 21; (1990); p. 3265 - 3271 View in Reaxys With lithium borohydride, sodium dichromate, sulfuric acid, boron trifluoride diethyl etherate, 1.) ethyl ether, 25-30 deg C, 2 h; 2.) water, ethyl ether, reflux, 2 h, Yield given. Multistep reaction Brown, Herbert C.; Garg, Chandra P.; Tetrahedron; vol. 42; nb. 20; (1986); p. 5511 - 5514 View in Reaxys With borane-THF, 4 A molecular sieve, tripropylammonium fluorochromate (VI), 1.) THF, 2 deg C, 1 h, 2.) CH2Cl2, reflux, 3 h, Yield given. Multistep reaction Parish, Edward J.; Ktzito, Stephen A.; Sun, Hang; Journal of Chemical Research - Part S; nb. 2; (1997); p. 64 65 View in Reaxys Reaction Steps: 3 1: 60 percent / OsO4, N-methylmorpholine N-oxide 2: 100 percent / pyridine 3: 68 percent / Et2AlSPh / hexane; CH2Cl2 / 0.5 h / 0 °C With pyridine, osmium(VIII) oxide, diethylaluminum benzenethiolate, 4-methylmorpholine N-oxide in hexane, dichloromethane Kanemoto, Shigekazu; Morizawa, Yoshitomi; Oshima, Koichiro; Nozaki, Hitosi; Bulletin of the Chemical Society of Japan; vol. 55; nb. 12; (1982); p. 3941 - 3942 View in Reaxys Reaction Steps: 2 1: HgO; diethyl ether; iodine 2: dimethylbenzylamine / Behandeln des Reaktionsprodukts mit verd. Schwefelsaeure With N,N'-dimethylbenzylamine, diethyl ether, iodine, mercury(II) oxide Le Brazidec; Bulletin de la Societe Chimique de France; vol. <4> 17; (1915); p. 101 View in Reaxys Reaction Steps: 2 1: borane-THF / 0 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 80 °C With borane-THF, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate Younai, Ashkaan; Fettinger, James C.; Shaw, Jared T.; Tetrahedron; vol. 68; nb. 22; (2012); p. 4320 - 4327 View in Reaxys Reaction Steps: 2 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C / Schlenk technique; Inert atmosphere 2: [Pd2H2(1,3-bis(diphenylphosphino)propane)3](TfO)2 / tetrahydrofuran / 4 h / 85 °C / Schlenk technique; Inert atmosphere; Glovebox With [Pd2H2(1,3-bis(diphenylphosphino)propane)3](TfO)2, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, dichloromethane

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Vyas, Devendra J.; Larionov, Evgeny; Besnard, Celine; Guenee, Laure; Mazet, Clement; Journal of the American Chemical Society; vol. 135; nb. 16; (2013); p. 6177 - 6183 View in Reaxys

I O

Rx-ID: 2340329 View in Reaxys 22/139 Yield

Conditions & References

10 %

With potassium tert-butylate in dimethyl sulfoxide, Time= 0.166667h, T= 70 °C , Microwave irradiation, Inert atmosphere Soria-Castro, Silvia M.; Caminos, Daniel A.; Penenory, Alicia B.; RSC Advances; vol. 4; nb. 34; (2014); p. 17490 - 17497 View in Reaxys With potassium tert-butylate, iron(II) chloride, 1.) DMSO, RT, 20 min, 2.) DMSO, RT, 20 min, Yield given. Multistep reaction Galli, Carlo; Gentili, Patrizia; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 6; (1993); p. 1135 - 1140 View in Reaxys

OH racemate

Rx-ID: 28591271 View in Reaxys 23/139 Yield

Conditions & References With (1S,3R,4S,5R,7R)-N-hydroxy-4-benzyl-1-isopropyl-2-azaadamantane, sodium hydrogencarbonate in dichloromethane, Time= 3h, T= -40 °C , Resolution of racemate, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Tomizawa, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Organic Letters; vol. 11; nb. 8; (2009); p. 1828 1831 View in Reaxys With (1R,3S,5S,7R,8S)-N-hydroxy-8-benzyl-1-methyl-2-azaadamantane, sodium hydrogencarbonate in dichloromethane, Time= 24h, T= -40 °C , Resolution of racemate, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Tomizawa, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Organic Letters; vol. 11; nb. 8; (2009); p. 1828 1831 View in Reaxys Typical procedure for kinetic resolution of alcohol General procedure: To a mixture of recemic-5 (15.3 mg, 0.093 mmol), (R,R)-1 (2.1 mg, 9.3 μmol, 10 mol percent), and K2CO3 (38.6 mg, 0.28 mmol, 3.0 equiv) in DCM (1.5 mL) was added PIFA (31.8 mg, 0.074 mmol, 0.8 equiv) at 0 °C. The resulting mixture was stirred at the same temperature for 6 h. The reaction was quenched with saturated aq. Na2S2O3 and extracted with CHCl3. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give a residue. The yield of the corresponding ketone was determined by 1H NMR integration with sorbic acid (10.3 mg, 0.093 mmol) as an internal standard. The residue was purified by prep. TLC (AcOEt/n–hexane = 1/5) to give recovered 5, whose ee and absolute configuration were determined by HPLC analysis with a chiral stationary phase (See Supplementary data). With C10H16NO5, potassium carbonate, bis-[(trifluoroacetoxy)iodo]benzene in dichloromethane, T= 0 °C , Resolution of racemate

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Hamada, Shohei; Wada, Yoshiyuki; Sasamori, Takahiro; Tokitoh, Norihiro; Furura, Takumi; Kawabata, Takeo; Tetrahedron Letters; vol. 55; nb. 11; (2014); p. 1943 - 1945 View in Reaxys With sodium hypochlorite, C17H22NO, sodium hydrogencarbonate, Time= 3h, T= 0 °C , Resolution of racemate, Inert atmosphere, Reagent/catalyst, Temperature, stereoselective reaction Tomizawa, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Organic Letters; vol. 16; nb. 18; (2014); p. 4968 4968 View in Reaxys

OH SR OH racemate

Rx-ID: 40165600 View in Reaxys 24/139 Yield

Conditions & References With trichloroisocyanuric acid, (1R,3S,6R,7S,8R)-7-benzyl-3-n-buthyl-4-oxa-5-azahomoadamantane, sodium hydrogencarbonate in dichloromethane, Time= 3h, T= -40 °C , Resolution of racemate, Inert atmosphere, stereoselective reaction Tomizawa, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Organic Letters; vol. 16; nb. 18; (2014); p. 4968 4968 View in Reaxys

OH racemate

Rx-ID: 40165608 View in Reaxys 25/139 Yield

Conditions & References With trichloroisocyanuric acid, (1R,3S,6R,7S,8R)-7-benzyl-3-methyl-4-oxa-5-azahomoadamantane, sodium hydrogencarbonate in dichloromethane, Time= 3h, T= -40 °C , Resolution of racemate, Inert atmosphere, Reagent/catalyst, Temperature, stereoselective reaction Tomizawa, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Organic Letters; vol. 16; nb. 18; (2014); p. 4968 4968 View in Reaxys

Rx-ID: 1752586 View in Reaxys 26/139 Yield 89 %

Conditions & References With palladium diacetate, tributylphosphine in tert-butyl alcohol, Time= 3.5h, Heating Kulasegaram, Sanjitha; Kulawiec, Robert J.; Journal of Organic Chemistry; vol. 62; nb. 19; (1997); p. 6547 - 6561 View in Reaxys

88 %

With indium(III) chloride in tetrahydrofuran, Time= 0.666667h, T= 25 °C , Rearrangement Ranu, Brindaban C.; Jana, Umasish; Journal of Organic Chemistry; vol. 63; nb. 23; (1998); p. 8212 - 8216 View in Reaxys

87 %

With Dowex-50W in water, Time= 0.5h, Heating, other 1-aryl-1,2-epoxides, Product distribution Ranu, Brindaban C.; Chakraborty, Rupak; Synthetic Communications; vol. 20; nb. 12; (1990); p. 1751 - 1756

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View in Reaxys 87 %

With Dowex-50W in water, Time= 0.5h, Heating Ranu, Brindaban C.; Chakraborty, Rupak; Synthetic Communications; vol. 20; nb. 12; (1990); p. 1751 - 1756 View in Reaxys

78 %

With pentacarbonyliron in benzene, Time= 6h, Irradiation Kobayashi, Tomoshige; Nitta, Makoto; Chemistry Letters; (1982); p. 325 - 328 View in Reaxys

73 %

With lithium perchlorate in diethyl ether, Time= 0.75h, T= 0 °C Sudha; Malola Narasimhan; Geetha Saraswathy; Sankararaman; Journal of Organic Chemistry; vol. 61; nb. 5; (1996); p. 1877 - 1879 View in Reaxys

62 %

With [Pd2H2(1,3-bis(diphenylphosphino)propane)3](TfO)2 in tetrahydrofuran, Time= 4h, T= 85 °C , Schlenk technique, Inert atmosphere, Glovebox Vyas, Devendra J.; Larionov, Evgeny; Besnard, Celine; Guenee, Laure; Mazet, Clement; Journal of the American Chemical Society; vol. 135; nb. 16; (2013); p. 6177 - 6183 View in Reaxys

62 %

With C45H104P6Pd2 in tetrahydrofuran, T= 85 - 140 °C Mazet, Clement; Chimia; vol. 67; nb. 9; (2013); p. 658 - 662 View in Reaxys

O S

O O

Rx-ID: 35959386 View in Reaxys 27/139 Yield

Conditions & References

70 %

With potassium phosphate, bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)], N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine in tert-butyl alcohol, T= 110 °C , Inert atmosphere, Glovebox Alsabeh, Pamela G.; Stradiotto, Mark; Angewandte Chemie - International Edition; vol. 52; nb. 28; (2013); p. 7242 - 7246; Angew. Chem.; vol. 125; nb. 28; (2013); p. 7383 - 7387 View in Reaxys

Rx-ID: 36708168 View in Reaxys 28/139 Yield 99 %

Conditions & References With sodium hypochlorite, 3-methyl-4-oxa-5-azahomoadamantane, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, Time= 0.333333h, T= 0 °C , Inert atmosphere Sasano, Yusuke; Murakami, Keiichi; Nishiyama, Tomohiro; Kwon, Eunsang; Iwabuchi, Yoshiharu; Angewandte Chemie - International Edition; vol. 52; nb. 48; (2013); p. 12624 - 12627; Angew. Chem.; vol. 125; nb. 48; (2013); p. 12856 - 12859,4 View in Reaxys

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O O

S O

Rx-ID: 33464920 View in Reaxys 29/139 Yield

Conditions & References Reaction Steps: 3 1: potassium thioacetate / N,N-dimethyl-formamide 2: borane-THF / 0 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 80 °C With borane-THF, potassium thioacetate, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate, N,N-dimethyl-formamide Younai, Ashkaan; Fettinger, James C.; Shaw, Jared T.; Tetrahedron; vol. 68; nb. 22; (2012); p. 4320 - 4327 View in Reaxys

OH racemate

Rx-ID: 33464927 View in Reaxys 30/139 Yield

Conditions & References Reaction Steps: 4 1: pyridine / 0 °C 2: potassium thioacetate / N,N-dimethyl-formamide 3: borane-THF / 0 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 80 °C With pyridine, borane-THF, potassium thioacetate, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate, N,N-dimethyl-formamide Younai, Ashkaan; Fettinger, James C.; Shaw, Jared T.; Tetrahedron; vol. 68; nb. 22; (2012); p. 4320 - 4327 View in Reaxys

O Cl Mg

Rx-ID: 33667041 View in Reaxys 31/139 Yield 63 %

Conditions & References Experimental procedure: General procedure: To a solution of ketone 1 (0.50 mmol) and isoxazolidine (0.75 mmol) in dry CH2Cl2 (5.0 mL) was added triphenylaluminum (1.0 mmol) dropwise at 0 °C. After stirring at room temperature for 8-16 h, the reaction was quenched by the addition of water. The resulting suspension was filtered and the filtrate was extracted with CHCl3. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by either flash column chromatography or PTLC to give 3. Stage 1: With aluminum (III) chloride in tetrahydrofuran Stage 2: With isoxazolidine in tetrahydrofuran, dichloromethane, T= 0 - 20 °C Miyoshi, Tetsuya; Sato, Shohei; Tanaka, Hiroya; Hasegawa, Chihiro; Ueda, Masafumi; Miyata, Okiko; Tetrahedron Letters; vol. 53; nb. 32; (2012); p. 4188 - 4191 View in Reaxys

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O Cl

Rx-ID: 9593944 View in Reaxys 32/139 Yield

Conditions & References

86 %

With sodium t-butanolate, [(IPr)Pd(acac)Cl] in toluene, Time= 2h, T= 60 °C Navarro, Oscar; Marion, Nicolas; Scott, Natalie M.; Gonzalez, Juan; Amoroso, Dino; Bell, Andrew; Nolan, Steven P.; Tetrahedron; vol. 61; nb. 41; (2005); p. 9716 - 9722 View in Reaxys

86 %

12 :Example 12 α-Phenylcyclohexanone (Table 2, entry 3). The procedure afforded 150 mg (86 percent) of the title compound. With sodium t-butanolate, [(IPr)Pd(acac)Cl] in toluene, Time= 2h, T= 60 °C , Product distribution / selectivity Patent; PROMERUS LLC; WO2006/128097; (2006); (A1) English View in Reaxys

70 %

With trans-[1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene]PdCl2(NC5H5), sodium t-butanolate in tetrahydrofuran, Time= 5h, T= 70 °C , Inert atmosphere Cao, Changsheng; Wang, Lingling; Cai, Zhengyuan; Zhang, Lingqiao; Guo, Jin; Pang, Guangsheng; Shi, Yanhui; European Journal of Organic Chemistry; nb. 8; (2011); p. 1570 - 1574 View in Reaxys With sodium amide Zhao, Kejun; Wang, Yongfeng; Zhao, Linxiang; Ji, Zhizhong; Li, Dan; Tisdale, Michael J.; Schwalbe, Carl H.; Farmaco; vol. 59; nb. 5; (2004); p. 373 - 379 View in Reaxys

Rx-ID: 10387611 View in Reaxys 33/139 Yield

Conditions & References

75 %

With tri-tert-butyl phosphine, tributyltin fluoride, tris(dibenzylideneacetone)dipalladium (0) in benzene, Time= 21h, Heating Iwama, Tetsuo; Rawal, Viresh H.; Organic Letters; vol. 8; nb. 25; (2006); p. 5725 - 5728 View in Reaxys With tris-(dibenzylideneacetone)dipalladium(0), tributyltin fluoride, triethylamine, tri tert-butylphosphoniumtetrafluoroborate in benzene, Time= 24h, T= 80 °C , Inert atmosphere Beck, Elizabeth M.; Hyde, Alan M.; Jacobsen, Eric N.; Organic Letters; vol. 13; nb. 16; (2011); p. 4260 - 4263 View in Reaxys

N O

Rx-ID: 30417715 View in Reaxys 34/139 Yield

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

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Miyoshi, Tetsuya; Miyakawa, Takayuki; Ueda, Masafumi; Miyata, Okiko; Angewandte Chemie - International Edition; vol. 50; nb. 4; (2011); p. 928 - 931 View in Reaxys

Rx-ID: 30813664 View in Reaxys 35/139 Yield

Conditions & References Reaction Steps: 2 1.1: iodine; magnesium / tetrahydrofuran / 14 h / 66 °C / Inert atmosphere 1.2: 6 h / 20 °C / Inert atmosphere 2.1: silica gel; pyridinium chlorochromate / dichloromethane / 14 h / 20 °C / Inert atmosphere With iodine, silica gel, magnesium, pyridinium chlorochromate in tetrahydrofuran, dichloromethane Poe, Sarah L.; Morken, James P.; Angewandte Chemie - International Edition; vol. 50; nb. 18; (2011); p. 4189 4192 View in Reaxys

Rx-ID: 30813707 View in Reaxys 36/139 Yield

Cl HO S O

Rx-ID: 32046890 View in Reaxys 37/139 Yield

Conditions & References

92 %

Stage 1: With tert-butylmagnesium chloride in tetrahydrofuran, T= -45 °C , Inert atmosphere Stage 2: With isopropylmagnesium chloride in tetrahydrofuran, T= -45 - 20 °C , Inert atmosphere Fukuda, Shigehiko; Tsuji, Kazuhito; Musashi, Jun; Nonaka, Ryo; Kimura, Tsutomu; Satoh, Tsuyoshi; Synthesis; nb. 22; (2011); p. 3615 - 3626; Art.No: F71511SS View in Reaxys

O S

Rx-ID: 32046927 View in Reaxys 38/139

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Yield

Conditions & References Reaction Steps: 3 1.1: N-chloro-succinimide / tetrachloromethane / 15 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / Inert atmosphere; Cooling 2.2: Inert atmosphere; Cooling 3.1: tert-butylmagnesium chloride / tetrahydrofuran / -45 °C / Inert atmosphere 3.2: -45 - 20 °C / Inert atmosphere With N-chloro-succinimide, tert-butylmagnesium chloride, lithium diisopropyl amide in tetrahydrofuran, tetrachloromethane Fukuda, Shigehiko; Tsuji, Kazuhito; Musashi, Jun; Nonaka, Ryo; Kimura, Tsutomu; Satoh, Tsuyoshi; Synthesis; nb. 22; (2011); p. 3615 - 3626; Art.No: F71511SS View in Reaxys

Cl S O

Rx-ID: 32046960 View in Reaxys 39/139 Yield

Conditions & References Reaction Steps: 2 1.1: lithium diisopropyl amide / tetrahydrofuran / Inert atmosphere; Cooling 1.2: Inert atmosphere; Cooling 2.1: tert-butylmagnesium chloride / tetrahydrofuran / -45 °C / Inert atmosphere 2.2: -45 - 20 °C / Inert atmosphere With tert-butylmagnesium chloride, lithium diisopropyl amide in tetrahydrofuran Fukuda, Shigehiko; Tsuji, Kazuhito; Musashi, Jun; Nonaka, Ryo; Kimura, Tsutomu; Satoh, Tsuyoshi; Synthesis; nb. 22; (2011); p. 3615 - 3626; Art.No: F71511SS View in Reaxys

Rx-ID: 32629657 View in Reaxys 40/139 Yield

Conditions & References

90 %

With [Ir(COD)((4S)-iPr-Phox)]tetrakis[(3,5-trifluoromethyl)phenyl]borate, hydrogen, N-ethyl-N,N-diisopropylamine in toluene, Time= 8h, T= 20 °C , p= 75007.5Torr , Autoclave Semeniuchenko, Volodymyr; Exner, Thomas E.; Khilya, Volodymyr; Groth, Ulrich; Applied Organometallic Chemistry; vol. 25; nb. 11; (2011); p. 804 - 809 View in Reaxys

Rx-ID: 29663108 View in Reaxys 41/139 Yield 51 %, 20 %, 22 %

Conditions & References With 1,3-dimethyl-2-imidazolidinone, toluene-4-sulfonic acid in dichloromethane, Time= 2h, T= 20 °C , regioselective reaction Chapman, Helen A.; Herbal, Karim; Motherwell, William B.; Synlett; nb. 4; (2010); p. 595 - 598; Art.No: D37609ST View in Reaxys

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B O

Rx-ID: 28530119 View in Reaxys 42/139 Yield

Conditions & References With diisopropylamine in 1,2-dichloro-ethane, Time= 18h, T= 60 °C , Inert atmosphere Peng, Cheng; Zhang, Wei; Yan, Guobing; Wang, Jianbo; Organic Letters; vol. 11; nb. 7; (2009); p. 1667 - 1670 View in Reaxys

OH racemate

Rx-ID: 28591273 View in Reaxys 43/139 Yield

Conditions & References With (1S,3R,4S,5R,7R)-N-hydroxy-4-benzyl-1-n-butyl-2-azaadamantane, sodium hydrogencarbonate in dichloromethane, Time= 3h, T= -40 °C , Resolution of racemate, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Tomizawa, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Organic Letters; vol. 11; nb. 8; (2009); p. 1828 1831 View in Reaxys

CrO 3 OH

Rx-ID: 28819266 View in Reaxys 44/139 Yield

Conditions & References

66 %

Stage 1: in dichloromethane, T= 20 °C , Inert atmosphere Stage 2: in dichloromethane, Time= 0.25h, T= 20 °C , Inert atmosphere Balamurugan, Rengarajan; Gudla, Vanajakshi; Organic Letters; vol. 11; nb. 14; (2009); p. 3116 - 3119 View in Reaxys

HO Br

racemate

Rx-ID: 26019865 View in Reaxys 45/139 Yield 84 %, 8 %

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

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Br HO

Rx-ID: 26019907 View in Reaxys 46/139 Yield

Conditions & References

85 %

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

O Cl

HO B HO O

Rx-ID: 25953407 View in Reaxys 47/139 Yield 75 %

Conditions & References With potassium phosphate, tetrakis(triphenylphosphine)nickel(0) in toluene, Time= 16h, T= 60 °C Liu, Chao; He, Chuan; Shi, Wei; Chen, Mao; Lei, Aiwen; Organic Letters; vol. 9; nb. 26; (2007); p. 5601 - 5604 View in Reaxys

O Br

Rx-ID: 2340230 View in Reaxys 48/139 Yield 72 %

Conditions & References With palladium diacetate, tri-tert-butyl phosphine, sodium t-butanolate in tetrahydrofuran, Time= 3h, T= 50 °C Kawatsura, Motoi; Hartwig, John F.; Journal of the American Chemical Society; vol. 121; nb. 7; (1999); p. 1473 1478 View in Reaxys

With sodium acetate, palladium diacetate, ethylene glycol, poly(ethylene glycol) in water, acetonitrile, Time= 0.5h, T= 180 °C , microwave irradiation Svennebring, Andreas; Garg, Neeraj; Nilsson, Peter; Hallberg, Anders; Larhed, Mats; Journal of Organic Chemistry; vol. 70; nb. 12; (2005); p. 4720 - 4725 View in Reaxys With dichlorobis(tri-O-tolylphosphine)palladium, tributyltin methoxide, 2.) toluene, 100 deg C , 5 h, Yield given. Multistep reaction Kosugi, Masanori; Hagiwara, Isao; Sumiya, Takashi; Migita, Toshihiko; Journal of the Chemical Society, Chemical Communications; nb. 7; (1983); p. 344 - 345 View in Reaxys

88 % Spectr.

With caesium carbonate, bis(phosphinite) PCR-pincer palladacycle in N,N-dimethyl-formamide, Time= 1.25h, T= 153 °C Churruca, Fatima; SanMartin, Raul; Tellitu, Imanol; Dominguez, Esther; Tetrahedron Letters; vol. 47; nb. 19; (2006); p. 3233 - 3237 View in Reaxys

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O Br

Rx-ID: 10044593 View in Reaxys 49/139 Yield

Conditions & References

88 %

With N-heterocyclic carbene-palladacycle, sodium t-butanolate in tetrahydrofuran, Time= 0.5h, T= 70 °C Navarro, Oscar; Marion, Nicolas; Oonishi, Yoshihiro; Kelly III, Roy A.; Nolan, Steven P.; Journal of Organic Chemistry; vol. 71; nb. 2; (2006); p. 685 - 692 View in Reaxys

O Cl

Rx-ID: 10044649 View in Reaxys 50/139 Yield 72 %

Conditions & References With N-heterocyclic carbene-palladacycle, sodium t-butanolate in tetrahydrofuran, Time= 1h, T= 70 °C Navarro, Oscar; Marion, Nicolas; Oonishi, Yoshihiro; Kelly III, Roy A.; Nolan, Steven P.; Journal of Organic Chemistry; vol. 71; nb. 2; (2006); p. 685 - 692 View in Reaxys

(1S)-2-amino-cyclohexanol-(1) O

Rx-ID: 12561138 View in Reaxys 51/139 Yield

Conditions & References Reaction Steps: 2 1: CuBr*Me2S / tetrahydrofuran / 0 °C 2: aq. Dess-Martin periodinane / CH2Cl2 / 20 °C With copper(I) bromide dimethylsulfide complex, Dess-Martin periodane in tetrahydrofuran, dichloromethane Pinard, Emmanuel; Ceccarelli, Simona M.; Stalder, Henri; Alberati, Daniela; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 2; (2006); p. 349 - 353 View in Reaxys

Br–+Mg

isopropyl magnesium halide O

Rx-ID: 12563598 View in Reaxys 52/139 Yield

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Rx-ID: 9880203 View in Reaxys 53/139 Yield

Conditions & References

83 %

With gallium(III) trichloride, methyl cyclohexane in 1,2-dichloro-ethane, Time= 12h, T= 80 °C Oshita, Masayuki; Okazaki, Takao; Ohe, Kouichi; Chatani, Naoto; Organic Letters; vol. 7; nb. 2; (2005); p. 331 334 View in Reaxys

O O–

F F

I+ O

Rx-ID: 10208969 View in Reaxys 54/139 Yield

Conditions & References

83 %

With lithium hexamethyldisilazane in tetrahydrofuran, N,N-dimethyl-formamide, T= -78 - -45 °C Aggarwal, Varinder K.; Olofsson, Berit; Angewandte Chemie - International Edition; vol. 44; nb. 34; (2005); p. 5516 - 5519 View in Reaxys

I+ I– O

Rx-ID: 10208980 View in Reaxys 55/139 Yield

Conditions & References With lithium hexamethyldisilazane in tetrahydrofuran, N,N-dimethyl-formamide, cooling Aggarwal, Varinder K.; Olofsson, Berit; Angewandte Chemie - International Edition; vol. 44; nb. 34; (2005); p. 5516 - 5519 View in Reaxys

Rx-ID: 9070770 View in Reaxys 56/139 Yield 79 %

Conditions & References With hydrogenchloride, dichloro bis(acetonitrile) palladium(II), copper dichloride in 1,4-dioxane, Time= 12h, T= 70 °C Wang, Xiang; Pei, Tao; Han, Xiaoqing; Widenhoefer, Ross A.; Organic Letters; vol. 5; nb. 15; (2003); p. 2699 2701 View in Reaxys

79 %

With hydrogenchloride, copper dichloride, dichloro bis(acetonitrile) palladium(II) in 1,4-dioxane, Time= 12h, T= 70 °C Han, Xiaoqing; Wang, Xiang; Pei, Tao; Widenhoefer, Ross A.; Chemistry - A European Journal; vol. 10; nb. 24; (2004); p. 6333 - 6342 View in Reaxys

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70 %

With chloro-trimethyl-silane, copper dichloride, dichloro bis(acetonitrile) palladium(II) in 1,4-dioxane, Time= 18h, T= 55 °C Pei, Tao; Widenhoefer, Ross A.; Chemical Communications; nb. 6; (2002); p. 650 - 651 View in Reaxys

halobenzene OH

racemate

Rx-ID: 9711016 View in Reaxys 57/139 Yield

Conditions & References

20 %, 55 %

Stage 1: With tetramethylpiperidine, tert.-butyl lithium in tetrahydrofuran, hexane, T= -40 °C Stage 2: in tetrahydrofuran, hexane, Time= 5h, T= -40 °C Tripathy, Sasmita; Reddy, Ranga; Durst, Tony; Canadian Journal of Chemistry; vol. 81; nb. 9; (2003); p. 997 1002 View in Reaxys

O O

N N

H N

H 2N

Rx-ID: 9014273 View in Reaxys 58/139 Yield

Conditions & References

3 %, 27 %, With 2,2'-azobis(isobutyronitrile), tri-n-butyl-tin hydride in benzene, Heating, Product distribution 6 %, 27 % Benati, Luisa; Leardini, Rino; Minozzi, Matteo; Nanni, Daniele; Spagnolo, Piero; Strazzari, Samantha; Zanardi, Giuseppe; Calestani, Gianluca; Tetrahedron; vol. 58; nb. 18; (2002); p. 3485 - 3492 View in Reaxys O O

racemate

Rx-ID: 8755105 View in Reaxys 59/139 Yield 95 %

Conditions & References Stage 1: With sodium ethanolate in ethanol, Time= 1h, T= 20 °C Stage 2: With hydrogenchloride in ethanol, T= 0 °C , Nef reaction Santos, Roberto P.; Lopes, Rosangela S. C.; Lopes, Claudio C.; Synthesis; nb. 6; (2001); p. 845 - 848 View in Reaxys

O N O

Rx-ID: 15426042 View in Reaxys 60/139 Yield

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Santos, Roberto P.; Lopes, Rosangela S. C.; Lopes, Claudio C.; Synthesis; nb. 6; (2001); p. 845 - 848 View in Reaxys Reaction Steps: 2 1: 1.) trifluoromethanesulfonic acid (TFSA) / 1.) CH2Cl2, -40 deg C, 2 h, 2.) -78 deg C to 20 deg C 2: H2O, trifluoromethanesulfonic acid (TFSA) With trifluorormethanesulfonic acid, water Okabe, Kazuaki; Ohwada, Tomohiko; Ohta, Toshiharu; Shudo, Koichi; Journal of Organic Chemistry; vol. 54; nb. 4; (1989); p. 733 - 734 View in Reaxys Reaction Steps: 2 1: 1) trifluoromethanesulfonic acid / 1) CH2Cl2, -40 deg C, 2 h 2: H2O With trifluorormethanesulfonic acid, water Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi; Tetrahedron; vol. 46; nb. 21; (1990); p. 7539 - 7555 View in Reaxys

[Ru(η3-CH2CHCH2)(η5-C5Me5)(η2-t-BuNC(Ph)=Nt-Bu)](1+)*PF6 (1-) O

Rx-ID: 15430396 View in Reaxys 61/139 Yield

Conditions & References Reaction Steps: 2 1.1: 72 percent / tetrahydrofuran / 2 h / -78 °C 2.1: EtONa / ethanol / 1 h / 20 °C 2.2: 95 percent / aq. HCl / ethanol / 0 °C With sodium ethanolate in tetrahydrofuran, ethanol, 2.2: Nef reaction Santos, Roberto P.; Lopes, Rosangela S. C.; Lopes, Claudio C.; Synthesis; nb. 6; (2001); p. 845 - 848 View in Reaxys

O Cl Br–+Mg

Rx-ID: 794922 View in Reaxys 62/139 Yield 68 %

Conditions & References in diethyl ether, benzene, Time= 8h, Heating Youssef, Abdel-Hamid A.; Sharaf, Saber M.; Hegazy, Fatma M. El; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 725 - 734 View in Reaxys

54 %

Nachtsheim, Corina M.; Frahm, August W.; Archiv der Pharmazie (Weinheim, Germany); vol. 322; (1989); p. 187 - 197 View in Reaxys

29 %

in tetrahydrofuran, benzene, Substitution Rettig, Martin; Sigrist, Andreas; Retey, Janos; Helvetica Chimica Acta; vol. 83; nb. 9; (2000); p. 2246 - 2265 View in Reaxys With diethyl ether, Kochen des vom Aether befreiten Reaktionsgemisches in Benzol Newman; Farbman; Journal of the American Chemical Society; vol. 66; (1944); p. 1550

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I N

Rx-ID: 8519414 View in Reaxys 63/139 Yield

Conditions & References

58 %

Stage 1: With titanocene(II) triethylphosphite complex in tetrahydrofuran, Time= 0.25h, T= 20 °C , complexation Stage 2: in tetrahydrofuran, Time= 2h, T= 20 °C , Alkylation Stage 3: With sodium hydroxide, Hydrolysis Takeda, Takeshi; Taguchi, Haruhiko; Fujiwara, Tooru; Tetrahedron Letters; vol. 41; nb. 1; (2000); p. 65 - 68 View in Reaxys

racemate

Rx-ID: 4944582 View in Reaxys 64/139 Yield

Conditions & References With tert.-butyl lithium in tetrahydrofuran, Time= 1h, T= 66 °C , Yield given. Yields of byproduct given Gokhale, Abha; Schiess, Peter; Helvetica Chimica Acta; vol. 81; nb. 2; (1998); p. 251 - 267 View in Reaxys With sodium tert-pentoxide in tetrahydrofuran, Time= 0.25h, T= 25 °C , Yield given. Yields of byproduct given Gokhale, Abha; Schiess, Peter; Helvetica Chimica Acta; vol. 81; nb. 2; (1998); p. 251 - 267 View in Reaxys

O Br

Rx-ID: 4877213 View in Reaxys 65/139 Yield

Conditions & References With water, sodium amide, magnesium bromide, multistep reaction; reactivity in the presence and absence of metal salts; also for cyclooctanone Fort, Yves; Christophe, Stephanie; Caubere, Paul; Journal of Chemical Research - Part S; nb. 9; (1997); p. 334 335 View in Reaxys

O O–

F F

I+ O

Rx-ID: 4877229 View in Reaxys 66/139 Yield

Conditions & References With lithium diisopropyl amide, 1.) THF, -78 deg C, 1 h; 2.) -35 deg C, 15 min, -78 deg C; 3.) -78 deg C, 15 min, r.t., 1 h, Product distribution Ryan, John H.; Stang, Peter J.; Tetrahedron Letters; vol. 38; nb. 28; (1997); p. 5061 - 5064

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View in Reaxys With lithium diisopropyl amide, 1.) THF, -78 deg C, 1 h; 2.) -35 deg C, 15 min, -78 deg C; 3.) -78 deg C, 15 min, r.t., 1 h, Yield given. Multistep reaction Ryan, John H.; Stang, Peter J.; Tetrahedron Letters; vol. 38; nb. 28; (1997); p. 5061 - 5064 View in Reaxys

O P

O O

Rx-ID: 4462136 View in Reaxys 67/139 Yield

Conditions & References

18 %, 28 %

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

18 %, 28 %

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

S HO

Rx-ID: 4490598 View in Reaxys 68/139 Yield

Conditions & References

61 %

With tetraethylammonium chloride in methanol, dichloromethane, electrolysis Kimura, Makoto; Kobayashi, Kazutaka; Yamamoto, Yasushi; Sawaki, Yasuhiko; Tetrahedron; vol. 52; nb. 12; (1996); p. 4303 - 4310 View in Reaxys With tetraethylammonium chloride in methanol, electrolysis, various solvents, Product distribution Kimura, Makoto; Kobayashi, Kazutaka; Yamamoto, Yasushi; Sawaki, Yasuhiko; Tetrahedron; vol. 52; nb. 12; (1996); p. 4303 - 4310 View in Reaxys

O P O

O O

Rx-ID: 4491875 View in Reaxys 69/139 Yield 18 %, 28 %

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

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Rx-ID: 4567712 View in Reaxys 70/139 Yield

Conditions & References

62 %, 25 %

With chloroperoxidase from fungus Caldaromyces fumago, potassium chloride, dihydrogen peroxide in water, Time= 4h Zaks, Aleksey; Yabannavar, Asha V.; Dodds, David R.; Evans, C. Anderson; Das, Pradip R.; Malchow, Rodney; Journal of Organic Chemistry; vol. 61; nb. 24; (1996); p. 8692 - 8695 View in Reaxys

40 %, 25 %

Rx-ID: 4567713 View in Reaxys 71/139 Yield

Conditions & References

41 %, 23 %

With chloroperoxidase from fungus Caldaromyces fumago, dihydrogen peroxide, potassium bromide in water, Time= 4h Zaks, Aleksey; Yabannavar, Asha V.; Dodds, David R.; Evans, C. Anderson; Das, Pradip R.; Malchow, Rodney; Journal of Organic Chemistry; vol. 61; nb. 24; (1996); p. 8692 - 8695 View in Reaxys

OH racemate

Rx-ID: 4568338 View in Reaxys 72/139 Yield 53.8 % Chromat., 45.1 % Chromat.

Conditions & References With (-)-sparteine in acetonitrile, electrolysis: 'H' type divided cell separated by membrane Nafion 117, NaClO4 as supporting electrolyte, TEMPO-modified grafite felt electrode, charge passed 1.17 F mol-1, electrolysis potential 0.60 V (vs. Ag/AgCl) Kashiwagi, Yoshitomo; Yanagisawa, Yoshinori; Kurashima, Futoshi; Anzai, Jun-Ichi; Osa, Tetsuo; Bobbitt, James M.; Chemical Communications; nb. 24; (1996); p. 2745 - 2746 View in Reaxys O

Rx-ID: 1792915 View in Reaxys 73/139

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Yield

Conditions & References With tetrabutyl-ammonium chloride, potassium acetate, palladium diacetate in N,N-dimethyl-formamide, Time= 72h, T= 80 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Larock, Richard C.; Yum, Eul K.; Yang, Hoseok; Tetrahedron; vol. 50; nb. 2; (1994); p. 305 - 322 View in Reaxys

Rx-ID: 4338641 View in Reaxys 74/139 Yield

Conditions & References With aluminum oxide, Time= 10h, T= 120 °C , var. time, var. temp., also CaO, K2O, and Pd doped catalysts, Product distribution, Mechanism Gorchakova, E. N.; Sibarov, D. A.; Fedorov, V. S.; Proskuryakov, V. A.; Russian Journal of Applied Chemistry; vol. 67; nb. 9.1; (1994); p. 1291 - 1295; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 67; nb. 9; (1994); p. 1471 - 1475 View in Reaxys

Rx-ID: 1649979 View in Reaxys 75/139 Yield

Conditions & References Yield given. Multistep reaction. Yields of byproduct given Gingrich, Henry L.; Huang, Qiurong; Morales, Angel L.; Jones, Maitland; Journal of Organic Chemistry; vol. 57; nb. 14; (1992); p. 3803 - 3806 View in Reaxys

Rx-ID: 1844846 View in Reaxys 76/139 Yield 96 %

Conditions & References With hydrogenchloride, Time= 8h, Ambient temperature Gingrich, Henry L.; Huang, Qiurong; Morales, Angel L.; Jones, Maitland; Journal of Organic Chemistry; vol. 57; nb. 14; (1992); p. 3803 - 3806 View in Reaxys

sodium disulfite solution O

Rx-ID: 19726072 View in Reaxys 77/139 Yield

Conditions & References Reaction Steps: 2 1: CuI 2: CrO3, H2SO4 / acetone

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With chromium(VI) oxide, copper(l) iodide, sulfuric acid in acetone Nishiyama; Park; Itoh; Tetrahedron Asymmetry; vol. 3; nb. 8; (1992); p. 1029 - 1034 View in Reaxys

Br–+Mg

etheric solution O

Rx-ID: 19729797 View in Reaxys 78/139 Yield

Conditions & References Reaction Steps: 2 1: CuI 2: CrO3, H2SO4 / acetone With chromium(VI) oxide, copper(l) iodide, sulfuric acid in acetone Nishiyama; Park; Itoh; Tetrahedron Asymmetry; vol. 3; nb. 8; (1992); p. 1029 - 1034 View in Reaxys

F Si

Rx-ID: 1983978 View in Reaxys 79/139 Yield

Conditions & References

88 %

in tetrahydrofuran, 1) < -38 deg C, 2 h 50 min 2) to 10 deg C, 2 h 3) r.t., 30 min Chen, Kuanchiang; Koser, Gerald F.; Journal of Organic Chemistry; vol. 56; nb. 20; (1991); p. 5764 - 5767 View in Reaxys

88 %

in tetrahydrofuran, other silyl enol ethers Chen, Kuanchiang; Koser, Gerald F.; Journal of Organic Chemistry; vol. 56; nb. 20; (1991); p. 5764 - 5767 View in Reaxys

F Si

Rx-ID: 1983979 View in Reaxys 80/139 Yield

Conditions & References

43 %

in tetrahydrofuran, -70 deg C to r.t., Yield given Chen, Kuanchiang; Koser, Gerald F.; Journal of Organic Chemistry; vol. 56; nb. 20; (1991); p. 5764 - 5767 View in Reaxys

O O

Rx-ID: 2044137 View in Reaxys 81/139 Yield

Conditions & References With water, Yield given. Yields of byproduct given

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Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi; Tetrahedron; vol. 46; nb. 21; (1990); p. 7539 - 7555 View in Reaxys

Rx-ID: 21274122 View in Reaxys 82/139 Yield

Conditions & References Reaction Steps: 2 1: 1.) trifluoromethanesulfonic acid (TFSA) / 1.) CH2Cl2, -40 deg C, 2 h, 2.) -78 deg C to 20 deg C 2: H2O, trifluoromethanesulfonic acid (TFSA) With trifluorormethanesulfonic acid, water Okabe, Kazuaki; Ohwada, Tomohiko; Ohta, Toshiharu; Shudo, Koichi; Journal of Organic Chemistry; vol. 54; nb. 4; (1989); p. 733 - 734 View in Reaxys Reaction Steps: 2 1: 1) trifluoromethanesulfonic acid / 1) CH2Cl2, -40 deg C, 2 h 2: H2O With trifluorormethanesulfonic acid, water Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi; Tetrahedron; vol. 46; nb. 21; (1990); p. 7539 - 7555 View in Reaxys

H HO

O HO

O racemate

Rx-ID: 1586499 View in Reaxys 83/139 Yield

Conditions & References With methane, hydrogen cation, p= 100Torr , var. reagents and pressures,, Product distribution, Mechanism Cecchi, P.; Pizzabiocca, A.; Renzi,G.; Chini, M.; Crotti, P.; et al.; Tetrahedron; vol. 45; nb. 13; (1989); p. 4227 4234 View in Reaxys

O O

Rx-ID: 2044136 View in Reaxys 84/139 Yield

Conditions & References With trifluorormethanesulfonic acid, water, Yield given Okabe, Kazuaki; Ohwada, Tomohiko; Ohta, Toshiharu; Shudo, Koichi; Journal of Organic Chemistry; vol. 54; nb. 4; (1989); p. 733 - 734 View in Reaxys

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O O

L-isomer

Rx-ID: 3894897 View in Reaxys 85/139 Yield

Conditions & References With lithium diisopropyl amide, 1.) THF, -78 deg C, 45 min, 2.) from -78 deg C to 0 deg C, 4 h, Yield given. Multistep reaction Paquette, Leo A.; Gilday, John P.; Maynard, George D.; Journal of Organic Chemistry; vol. 54; nb. 21; (1989); p. 5044 - 5053 View in Reaxys

O O

O N

racemate

Rx-ID: 2084513 View in Reaxys 86/139 Yield

Conditions & References With hydrogenchloride, 1.) hexane, 0 deg C, 30 min, 2.) hexane/diethyl ether, 0 deg C, Yield given. Multistep reaction. Yields of byproduct given Pecunioso, Angelo; Menicagli, Rita; Journal of Organic Chemistry; vol. 53; nb. 1; (1988); p. 45 - 49 View in Reaxys

racemate

Rx-ID: 1586498 View in Reaxys 87/139 Yield

Conditions & References With oxygen, p= 4Torr , Irradiation, effect of gas phase acid-induced ring opening, Product distribution, Mechanism Crotti, P.; Macchia, F.; Pizzabiocca, A.; Renzi, G.; Speranza, M.; Tetrahedron Letters; vol. 28; nb. 29; (1987); p. 3393 - 3396 View in Reaxys

O O O

Rx-ID: 2827097 View in Reaxys 88/139 Yield 96 %

Conditions & References With hydrogenchloride in tetrahydrofuran, water, Time= 31h, Ambient temperature Syper, Ludwik; Tetrahedron; vol. 43; nb. 12; (1987); p. 2853 - 2872 View in Reaxys

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Ph2CuLi O

Rx-ID: 6524254 View in Reaxys 89/139 Yield

Conditions & References With hydrogenchloride, 1.) THF, from -23 deg C to RT, 3 h, 2.) THF, 6 h, Yield given. Multistep reaction Rathke, Michael W.; Vogiazoglou, Demetris; Journal of Organic Chemistry; vol. 52; nb. 16; (1987); p. 3697 - 3698 View in Reaxys

O Br

Br–+Mg

Rx-ID: 1550174 View in Reaxys 90/139 Yield

Conditions & References Mechanism Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys 1.) ether, r.t., 2 h; 2.) THF, reflux, 12 h, Yield given. Multistep reaction. Yields of byproduct given Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys

N– Br–

Mg2+

Rx-ID: 1710707 View in Reaxys 91/139 Yield

Conditions & References

19 %

With reduced phosphine-ligated nickel dihalide, oxonium Swindell, Charles S.; Duffy, Ruth H.; Heterocycles; vol. 24; nb. 12; (1986); p. 3373 - 3377 View in Reaxys

O Cl

Rx-ID: 3794821 View in Reaxys 92/139 Yield

Conditions & References 1.) ether; 2.) benzene, reflux, Yield given. Multistep reaction. Yields of byproduct given Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys 1.) ether, r.t., 2 h; 2.) THF, reflux, 12 h, Yield given. Multistep reaction. Yields of byproduct given Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605

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O Cl

Br–+Mg

Rx-ID: 3794858 View in Reaxys 93/139 Yield

Conditions & References various educt ratios; study of solvent effect using various solvents, Product distribution, Mechanism Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys 1.) ether; 2.) benzene, reflux, Yield given. Multistep reaction. Yields of byproduct given Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys 1.) ether, r.t., 2 h; 2.) THF, reflux, 12 h, Yield given. Multistep reaction. Yields of byproduct given Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys

Rx-ID: 1579953 View in Reaxys 94/139 Yield

Conditions & References With HgO*HBF4 in tetrahydrofuran, Time= 4h, T= 70 °C , Yield given. Yields of byproduct given Barluenga, Jose; Alonso-Cires, Luisa; Campos, Pedro J.; Asensio, Gregorio; Tetrahedron; vol. 40; nb. 13; (1984); p. 2563 - 2568 View in Reaxys

O O

Rx-ID: 1870906 View in Reaxys 95/139 Yield

Conditions & References With HgO*HBF4, Time= 4h, T= 70 °C , Yield given. Yields of byproduct given Barluenga, Jose; Alonso-Cires, Luisa; Campos, Pedro J.; Asensio, Gregorio; Tetrahedron; vol. 40; nb. 13; (1984); p. 2563 - 2568 View in Reaxys O O

Rx-ID: 2013455 View in Reaxys 96/139

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Yield

Conditions & References With ammonium peroxydisulfate, copper diacetate in water, acetic acid, T= 100 °C , Yield given. Yields of byproduct given Walling, Cheves; El-Taliawi, Gamil M.; Amarnath, Kalyani; Journal of the American Chemical Society; vol. 106; (1984); p. 7573 - 7578 View in Reaxys

Rx-ID: 2015424 View in Reaxys 97/139 Yield

I O

Rx-ID: 2340330 View in Reaxys 98/139 Yield

Conditions & References

75 % Chromat., 25 % Chromat.

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

Rx-ID: 3843387 View in Reaxys 99/139 Yield

Conditions & References

54 %

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

54 %

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

O Br Br

Rx-ID: 3943814 View in Reaxys 100/139

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Yield

Conditions & References With magnesium, 1.) Et2O, 2.) Et2O, reflux; benzene, reflux, 8 h, Yield given. Multistep reaction Hoshi, Nobuto; Sato, Kazuhiro; Uda, Hisashi; Hagiwara, Hisahiro; Journal of Chemical Research, Miniprint; nb. 12; (1984); p. 3501 - 3596 View in Reaxys

Cu(OAc)2 O

Rx-ID: 7048471 View in Reaxys 101/139 Yield

Conditions & References With ammonium peroxydisulfate in water, acetic acid, T= 100 °C , Yield given. Yields of byproduct given Walling, Cheves; El-Taliawi, Gamil M.; Amarnath, Kalyani; Journal of the American Chemical Society; vol. 106; (1984); p. 7573 - 7578 View in Reaxys

Rx-ID: 19228494 View in Reaxys 102/139 Yield

Conditions & References Reaction Steps: 2 1: (NH4)2S2O8, Cu(OAc)2 / acetic acid; H2O / 100 °C 2: (NH4)2S2O8, Cu(OAc)2 / acetic acid; H2O / 100 °C With ammonium peroxydisulfate, copper diacetate in water, acetic acid Walling, Cheves; El-Taliawi, Gamil M.; Amarnath, Kalyani; Journal of the American Chemical Society; vol. 106; (1984); p. 7573 - 7578 View in Reaxys Reaction Steps: 2 1: (NH4)2S2O8, Cu(OAc)2 / acetic acid; H2O / 100 °C 2: (NH4)2S2O8 / acetic acid; H2O / 100 °C With ammonium peroxydisulfate, copper diacetate in water, acetic acid Walling, Cheves; El-Taliawi, Gamil M.; Amarnath, Kalyani; Journal of the American Chemical Society; vol. 106; (1984); p. 7573 - 7578 View in Reaxys Reaction Steps: 2 1: (NH4)2S2O8, Cu(OAc)2 / acetonitrile; H2O / 100 °C 2: (NH4)2S2O8, Cu(OAc)2 / acetic acid; H2O / 100 °C With ammonium peroxydisulfate, copper diacetate in water, acetic acid, acetonitrile Walling, Cheves; El-Taliawi, Gamil M.; Amarnath, Kalyani; Journal of the American Chemical Society; vol. 106; (1984); p. 7573 - 7578 View in Reaxys Reaction Steps: 2 1: (NH4)2S2O8, Cu(OAc)2 / acetonitrile; H2O / 100 °C 2: (NH4)2S2O8 / acetic acid; H2O / 100 °C With ammonium peroxydisulfate, copper diacetate in water, acetic acid, acetonitrile

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Walling, Cheves; El-Taliawi, Gamil M.; Amarnath, Kalyani; Journal of the American Chemical Society; vol. 106; (1984); p. 7573 - 7578 View in Reaxys

Rx-ID: 1710393 View in Reaxys 103/139 Yield

Conditions & References With dichlorobis(tri-O-tolylphosphine)palladium, tributyltin fluoride in benzene, Time= 3h, Heating Kuwajima, Isao; Urabe, Hirokazu; Journal of the American Chemical Society; vol. 104; nb. 24; (1982); p. 6831 6833 View in Reaxys O

Rx-ID: 2013456 View in Reaxys 104/139 Yield

Conditions & References With cobalt naphthenate, oxygen in chloroform, T= 50 °C , Yields of byproduct given Sethi, Shanti C.; Natu, Arun D.; Wadia, Murzban S.; Heterocycles; vol. 18; (1982); p. 221 - 228 View in Reaxys

O O

HO racemate

Rx-ID: 2199920 View in Reaxys 105/139 Yield

Conditions & References

68 %

With diethylaluminum benzenethiolate in hexane, dichloromethane, Time= 0.5h, T= 0 °C Kanemoto, Shigekazu; Morizawa, Yoshitomi; Oshima, Koichiro; Nozaki, Hitosi; Bulletin of the Chemical Society of Japan; vol. 55; nb. 12; (1982); p. 3941 - 3942 View in Reaxys

HO racemate

Rx-ID: 19031653 View in Reaxys 106/139 Yield

Conditions & References Reaction Steps: 2 1: 100 percent / pyridine 2: 68 percent / Et2AlSPh / hexane; CH2Cl2 / 0.5 h / 0 °C With pyridine, diethylaluminum benzenethiolate in hexane, dichloromethane Kanemoto, Shigekazu; Morizawa, Yoshitomi; Oshima, Koichiro; Nozaki, Hitosi; Bulletin of the Chemical Society of Japan; vol. 55; nb. 12; (1982); p. 3941 - 3942 View in Reaxys

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O S

N N

Rx-ID: 1544232 View in Reaxys 107/139 Yield

Conditions & References Yield given. Multistep reaction Baldwin, Jack E.; Bottaro, Jeffrey C.; Journal of the Chemical Society, Chemical Communications; nb. 21; (1981); p. 1121 - 1122 View in Reaxys

N E

N+ I–

NH 2

Rx-ID: 2444885 View in Reaxys 108/139 Yield

Conditions & References With sodium tetrahydroborate, sodium methylate, 1) MeOH, below 10 deg C to 40 deg C, 2) MeOH, below 10 deg C, 2 h, Yield given. Multistep reaction. Yields of byproduct given Parcell, Robert F.; Sanchez, Joseph P.; Journal of Organic Chemistry; vol. 46; (1981); p. 5229 - 5231 View in Reaxys

N E

N+

I– H 2N

Rx-ID: 2444886 View in Reaxys 109/139 Yield

Conditions & References With hydrogenchloride, sodium ethanolate, 1) EtOH, reflux, 1 h, 2) EtOH, below 25 deg C, Yield given. Multistep reaction. Yields of byproduct given Parcell, Robert F.; Sanchez, Joseph P.; Journal of Organic Chemistry; vol. 46; (1981); p. 5229 - 5231 View in Reaxys

N E

N+

I–

Rx-ID: 2444887 View in Reaxys 110/139 Yield

Conditions & References With hydrogenchloride, sodium methylate, 1) MeOH, below 10 deg C to 40 deg C, 2) MeOH, below 10 deg C,, Yield given. Multistep reaction. Yields of byproduct given Parcell, Robert F.; Sanchez, Joseph P.; Journal of Organic Chemistry; vol. 46; (1981); p. 5229 - 5231 View in Reaxys

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O HN NH O

Rx-ID: 18621655 View in Reaxys 111/139 Yield

Conditions & References Reaction Steps: 2 1: 1) PCl5 / 1) CH2Cl2 With phosphorus pentachloride Baldwin, Jack E.; Bottaro, Jeffrey C.; Journal of the Chemical Society, Chemical Communications; nb. 21; (1981); p. 1121 - 1122 View in Reaxys

N E

Rx-ID: 19164230 View in Reaxys 112/139 Yield

Conditions & References Reaction Steps: 2 1: 76 percent / acetonitrile / A) 43 deg C, 2 h, b) 70 deg C, 3 h 2: 1) NaOMe, 2) NaBH4 / 1) MeOH, below 10 deg C to 40 deg C, 2) MeOH, below 10 deg C, 2 h With sodium tetrahydroborate, sodium methylate in acetonitrile Parcell, Robert F.; Sanchez, Joseph P.; Journal of Organic Chemistry; vol. 46; (1981); p. 5229 - 5231 View in Reaxys Reaction Steps: 2 1: 76 percent / acetonitrile / A) 43 deg C, 2 h, b) 70 deg C, 3 h 2: 1) NaOEt, 2) 4.0 M HCl / 1) EtOH, reflux, 1 h, 2) EtOH, below 25 deg C With hydrogenchloride, sodium ethanolate in acetonitrile Parcell, Robert F.; Sanchez, Joseph P.; Journal of Organic Chemistry; vol. 46; (1981); p. 5229 - 5231 View in Reaxys Reaction Steps: 2 1: 76 percent / acetonitrile / A) 43 deg C, 2 h, b) 70 deg C, 3 h 2: 1) NaOMe, 2) 3.0 M HCl / 1) MeOH, below 10 deg C to 40 deg C, 2) MeOH, below 10 deg C, With hydrogenchloride, sodium methylate in acetonitrile Parcell, Robert F.; Sanchez, Joseph P.; Journal of Organic Chemistry; vol. 46; (1981); p. 5229 - 5231 View in Reaxys

(v2) (v4)H

H(v4) (v2)

H H H

O racemate

Rx-ID: 26842900 View in Reaxys 113/139 Yield

Conditions & References With chromic acid, oxidn.;

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Brown, H. C.; Gard, C. P.; Journal of the American Chemical Society; vol. 83; (1961); p. 2951 - 2952 ; (from Gmelin) View in Reaxys With H2CrO4, oxidn.; vol. B: B-Verb.14; 5.6, page 212 - 224 ; (from Gmelin) View in Reaxys

Br–+Mg

(+-)-2c-chloro-1-phenyl-cyclohexan-r-ol O

Rx-ID: 6524253 View in Reaxys 114/139 Yield

Conditions & References With diethyl ether, benzene Hussey; Herr; Journal of Organic Chemistry; vol. 24; (1959); p. 843 View in Reaxys

O N

Rx-ID: 49015 View in Reaxys 115/139 Yield

Conditions & References With methanol Gutsche; Jason; Journal of the American Chemical Society; vol. 78; (1956); p. 1184,1186 View in Reaxys

Ag2O HO

Rx-ID: 7987438 View in Reaxys 116/139 Yield

Conditions & References Curtin; Schmukler; Journal of the American Chemical Society; vol. 77; (1955); p. 1105,1108 View in Reaxys

H 2N O

O HO

racemate

1-phenyl-cyclohexane-1,2-diolene

Rx-ID: 7987439 View in Reaxys 117/139 Yield

Conditions & References Curtin; Schmukler; Journal of the American Chemical Society; vol. 77; (1955); p. 1105,1108 View in Reaxys

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O Ag+

O–

O HO

Rx-ID: 7987440 View in Reaxys 118/139 Yield

Conditions & References Curtin; Schmukler; Journal of the American Chemical Society; vol. 77; (1955); p. 1105,1108 View in Reaxys

H 2N HO

O N

Rx-ID: 7991498 View in Reaxys 119/139 Yield

Conditions & References Elphimoff-Felkin; Tchoubar; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 237; (1953); p. 726 View in Reaxys

(+-)-6-phenyl-cyclohex-3-enone O

Rx-ID: 6524249 View in Reaxys 120/139 Yield

Conditions & References With palladium on activated charcoal, ethanol, Hydrogenation Wildman; Wildman; Journal of Organic Chemistry; vol. 17; (1952); p. 581,588 View in Reaxys

N2O O

Rx-ID: 7250185 View in Reaxys 121/139 Yield

Conditions & References T= 300 °C , p= 367754Torr Bridson-Jones; Buckley; Journal of the Chemical Society; (1951); p. 3009,3010,1014 View in Reaxys

N O

O O

Rx-ID: 351298 View in Reaxys 122/139 Yield

Conditions & References Bachmann et al.; Journal of the American Chemical Society; vol. 72; (1950); p. 1995,1998 View in Reaxys

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O O

Rx-ID: 490021 View in Reaxys 123/139 Yield

Conditions & References With hydrogenchloride, acetic acid Bachmann et al.; Journal of the American Chemical Society; vol. 72; (1950); p. 1995,1998 View in Reaxys

Rx-ID: 553437 View in Reaxys 124/139 Yield

Conditions & References T= 155 °C Goldschmidt; Veer; Recueil des Travaux Chimiques des Pays-Bas; vol. 67; (1948); p. 489,506 View in Reaxys

1-phenyl-cyclohexanediol-(1.2)-mixture of/the/ stereoisomer(ic)/s O

Rx-ID: 6524251 View in Reaxys 125/139 Yield

Conditions & References With oxalic acid, T= 155 °C Goldschmidt; Veer; Recueil des Travaux Chimiques des Pays-Bas; vol. 67; (1948); p. 489,506 View in Reaxys

Rx-ID: 7155118 View in Reaxys 126/139 Yield

Conditions & References auf Siedetemperatur Goldschmidt; Veer; Recueil des Travaux Chimiques des Pays-Bas; vol. 67; (1948); p. 489,506 View in Reaxys

racemate

Rx-ID: 171767 View in Reaxys 127/139 Yield

Conditions & References Eindampfen, Erhitzen auf 160grad und anschliessendes Behandeln mit Wasser Tiffeneau; Tchoubar; Le Tellier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 217; (1943); p. 588

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View in Reaxys

racemate

Rx-ID: 171768 View in Reaxys 128/139 Yield

2-chloro-1-phenyl-cyclohexanole-(1)-stereoisomer(ic)/s O

Rx-ID: 6524252 View in Reaxys 129/139 Yield

Conditions & References With diethyl ether, ethylmagnesium bromide, Erwaermen der vom Loesungsmittel befreiten Reaktionsgemische auf 100grad Tiffeneau; Tchoubar; Le Tellier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 217; (1943); p. 588 View in Reaxys

(+-)-cis-phenyl-cyclohexanol-(2) O

Rx-ID: 6524250 View in Reaxys 130/139 Yield

Conditions & References With chromium(VI) oxide, acetic acid Price; Karabinos; Journal of the American Chemical Society; vol. 62; (1940); p. 1159 View in Reaxys

O HO O

OH racemate

Rx-ID: 438748 View in Reaxys 131/139 Yield

Conditions & References With chromium(VI) oxide, acetic acid Cook; Hewett; Lawrence; Journal of the Chemical Society; (1936); p. 71,76 View in Reaxys

O O

CrO3

racemate

Rx-ID: 7982495 View in Reaxys 132/139

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Yield

Conditions & References Cook; Hewett; Lawrence; Journal of the Chemical Society; (1936); p. 71,76 View in Reaxys

(+-)-1.2-epoxy-1-phenyl-cyclohexane O

Rx-ID: 6524248 View in Reaxys 133/139 Yield

Conditions & References With zinc(II) chloride Levy; Sfiras; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1830,1834 View in Reaxys Levy; Sfiras; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1830,1834 View in Reaxys With pumice stone, sulfuric acid Levy; Sfiras; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1830,1834 View in Reaxys

H N

NH 2

E O

Rx-ID: 125579 View in Reaxys 134/139 Yield

Conditions & References bei der Destillation Levy; Sfiras; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 187; (1928); p. 46; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1834 View in Reaxys

1.2-oxido-1-phenyl-cyclohexane O

Rx-ID: 6676468 View in Reaxys 135/139 Yield

Conditions & References With zinc(II) chloride, bei der Destillation Levy; Sfiras; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 187; (1928); p. 46; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1834 View in Reaxys

O Ag+

O–

O HO

Rx-ID: 7991871 View in Reaxys 136/139 Yield

Conditions & References Boeeseken; Chemische Berichte; vol. 56; (1923); p. 2410; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 687 View in Reaxys

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Le Brazidec; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 159; (1914); p. 775,776; Bulletin de la Societe Chimique de France; vol. <4> 17; (1915); p. 108,109 View in Reaxys

chromium trioxide OH

Rx-ID: 7155119 View in Reaxys 137/139 Yield

Conditions & References v. Braun; Gruber; Kirschbaum; Chemische Berichte; vol. 55; (1922); p. 3672 View in Reaxys

Rx-ID: 465259 View in Reaxys 138/139 Yield

Conditions & References With silver nitrate Le Brazidec; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 159; (1914); p. 775,776; Bulletin de la Societe Chimique de France; vol. <4> 17; (1915); p. 108,109 View in Reaxys With N,N'-dimethylbenzylamine, durch Destillation unter vermindertem Druck Le Brazidec; Bulletin de la Societe Chimique de France; vol. <4> 17; (1915); p. 101 View in Reaxys With N,N'-dimethylbenzylamine, Behandeln des Reaktionsprodukts mit verd. Schwefelsaeure Le Brazidec; Bulletin de la Societe Chimique de France; vol. <4> 17; (1915); p. 101 View in Reaxys Reaction Steps: 2 1: AgNO3 2: diluted sulfuric acid With sulfuric acid, silver nitrate Le Brazidec; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 159; (1914); p. 775,776; Bulletin de la Societe Chimique de France; vol. <4> 17; (1915); p. 108,109 View in Reaxys

OH HO

S OO

Rx-ID: 7541697 View in Reaxys 139/139 Yield

Conditions & References Le Brazidec; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 159; (1914); p. 775,776; Bulletin de la Societe Chimique de France; vol. <4> 17; (1915); p. 108,109 View in Reaxys

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