Oxidation by cobalt(III) acetate. Part 8. Effects of substituents on product distributions in oxidation of aromatic olefins by cobalt(III) acetate

Abstract

Oxidation of aromatic olefins by cobalt(III) acetate in acetic acid under nitrogen gave both allylic acetates and glycol monoacetates. Disubstituted olefins were oxidized by the oxidant to give predominantly allylic acetates. Glycol monoacetates were minor products except for the case of 1-phenylisobutene which was slowly oxidized to give the corresponding glycol monoacetate. In the oxidation of tri- and terra-substituted olefins, the yield of glycol monoacetate increased at the expense of that of allylic acetate. A mechanism, in which the reaction proceeds through a Co-co-ordinated radical cation formed by an one-electron abstraction from olefin by cobalt(III) acetate, is suggested.