Acyl transfer accompanying the oxidation of monocarboxylic esters of hydroquinones

Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690000079

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.

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