Acyl transfer accompanying the oxidation of monocarboxylic esters of hydroquinones

Abstract

Benzoyl transfer accompanies the oxidation of monobenzoates of hydroquinones. Oxidising agents used in the present investigation were ceric ion, thallic ion, N-bromosuccinimide, bromine, a high potential quinone, and lithium periodate. Evidence is presented that acylium intermediates are formed in the oxidations with ceric ion: thallic ion oxidations are catalysed by thallous ion, and acyl transfer in these cases appears to require attack of solvent on a thallic ion–substrate complex.