Journal of Organic Chemistry p. 528 - 531 (1985)
Update date:2022-08-10
Topics:
Barry, John E.
Finkelstein, Manuel
Moore, W. Michael
Ross, Sidney D.
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.
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