The Journal of Organic Chemistry

Single electron transfer in nucleophilic aliphatic substitution. Evidence for single electron transfer in the reactions of 1-halonorbornanes with various nucleophiles

EC Ashby, X Sun, JL Duff

Index: Ashby, E. C.; Sun, Xiaojing; Duff, J. L. Journal of Organic Chemistry, 1994 , vol. 59, # 6 p. 1270 - 1278

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Citation Number: 33

Abstract

A series of 1-halonorbornanes was used as a model system in reactions with several nucleophiles in order to determine the involvement of single electron transfer (SET) in nucleophilic aliphatic substitution in the absence of light. The 1-halonorbornanes were allowed to react with MesSn-, PhzP-, Alh-, N (iPr) 2-, SPh-, and the 2-nitropropyl anion in ether solvents at room temperature to 0 OC. The results of product analyses, the use of ...