Electroorganic reactions. Part 58. Revisiting the cleavage of oxalateesterradical-anions

Abstract

Electrochemically-generated radical-anions of oxalate esters undergo cleavage. For those of ethyl 4-substituted benzyl oxalates the rates of cleavage have been measured by cyclic voltammetry combined with digital simulation. Consideration of substituent effects and earlier product studies presents compelling evidence for an EC mechanism with the cleavage resulting in oxalate anions and benzyl radicals.