The Journal of Organic Chemistry

New method for the facile reduction of. alpha.-nitro sulfones to nitroalkanes via an electron-transfer-hydrogen atom abstraction mechanism

J Chen, DD Tanner

Index: Chen, Jian; Tanner, Dennis D. Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 3897 - 3900

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Citation Number: 26

Abstract

The mechanism for the reduction of several a-nitro sulfones with 1, 3-dimethyl-2- phenylbenzimidazoline(DMBI) was investigated. The reduction proceeds by a free-radical chain process where the initiation step and one of the propagation steps involve single electron transfer reactions. The synthetic utility of the reduction was investigated. a-Nitro sulfones are potentially useful substrates in organic synthesis.(Arylsulfony1) nitromethane ...