Electrochemical reduction of N-bromosuccinimide. Reaction mechanism for formation of the succinimidyl radical

…, SD Ross, L Eberson, L Joensson

Index: Barry, John E.; Finkelstein, Manuel; Moore, W. Michael; Ross, Sydney D.; Eberson, Lennart; Joensson, Lennart Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1292 - 1298

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Citation Number: 26

Abstract

The electrochemical reduction of N-bromosuccinimide in acetonitrile at a platinum cathode generates the succinimidyl radical in an overall process for which the n value is 1. The succinimide anion, generated by two-electron reduction of N-bromosuccinimide, is an intermediate in this process, and its electron-transfer reaction with the N-bromo imide generates the radical. The intermediacy of the succinimide anion is demonstrated by ...