Bulletin of the Chemical Society of Japan p. 737 - 746 (1987)
Update date:2022-08-03
Topics:
Chikashita, Hidenori
Nishida, Shuichi
Miyazaki, Makoto
Morita, Yasuhiro
Itoh, Kazuyoshi
2-Phenylbenzimidazoline (PBI) as a mild, selective, and convenient reducing agent was efficiently generated in situ from o-phenylenediamine and benzaldehyde in alcohols.A generally applicable method for the selective reduction of carbon-carbon double bonds of a variety of electron-deficient olefins with an alcoholic solution of PBI is described.The reduction of α,β-unsaturated ketones to the corresponding saturated ketones could also be accomplished (but, less effectively) with PBI with the aid of a Lewis-acid catalyst. 1-Methyl-2-(o-nitrophenyl)benzimidazoline prepared and isolated by the reaction of o-nitrobenzaldehyde with N-methyl-o-phenylenediamine reduced benzylidenemalononitrile to give benzylmalononitrile and 1-methyl-2-(o-nitrophenyl)benzimidazoline in high yields.This shows the validity of PBI to be the actual reducing species in the present reduction system.From a mechanistic study, the present reductions could be interpreted in terms of a mechanism involving a synchronous transport of a pair of hydrogens or a sequential transfer of a hydride and a proton from PBI to the olefins.
View MoreContact:86-551-63540590
Address:No 1388 Furong Rd., Hefei, Anhui, China
Xi'an caijing Opto-Electrical Science & Technology Co., LTD
Contact:+86-29-88294447
Address:NO.168 Zhangba Rd. East, Xi'an, P.R.China
Jiangxi Dongbang Pharmaceutical Co., Ltd.
Contact:+86-795-4433603, 4433388
Address:Fengxin Industrial Park, Fengxin County, Jiangxi Province, P.R.C
Sichuan Highlight Fine Chemicals Co., Ltd.
Contact:+86-28-8525 1605
Address:A5-102 Airport base,388 West Airport Huang He Zhong Lu,2 Section
Contact:86-0510-85133006
Address:hubin road NO157
Doi:10.1023/A:1017546730492
(2001)Doi:10.1016/S0020-1693(01)00471-6
(2001)Doi:10.1039/d1sc00694k
(2021)Doi:10.1021/jm00274a040
(1972)Doi:10.1021/ol0165286
(2001)Doi:10.1016/S0040-4039(01)01437-X
(2001)