Rates and Mechanism in the Electron Transfer Mediated Reduction of N-Chlorosuccinimide by Succcinimide Anion.

Article abstract of DOI:10.1021/jo00204a021

The electrochemical reduction of N-chlorosuccinimide in acetonitrile at a platinum cathode parallels the reduction of N-bromosuccinimide.The overall n value is 1; the succinimide anion, generated by a two-electron reduction of N-chlorosuccinimide, is an intermediate; homogeneous electron transfer from the succinimide anion to N-chlorosuccinimide generates the succinimidyl radical, which is the precursor for the products formed.The reduction of N-chlorosuccinimide by the succinimide anion, added as a quaternary ammonium succinimide, in a homogeneous chemical system is significantly different from the comparable reaction with N-bromosuccinimide.Rate constants for the pertinent reactions have been measured, and reaction mechanism has been discussed.