Abstract

The formation of hydroxy acetates in the reaction of some alkenes with lead(IV), cobalt(III), and manganese(III) in acetic acid is demonstrated to involve the intermediacy of alkene radical-cations. A study employing a range of aryl-substituted alkenes has shown that there is an inverse relationship between the yield of hydroxy acetate and the ionisation potential of the organic substrate. The electron deficiency in the radica-cations derived from these alkenes appears to be localised on the double bond: no evidence could be obtained for reaction at the aromatic ring. The introduction of a chlorine atom into this ring had the effect of repressing electron-transfer in cobalt(III) and manganese(III) oxidations but not in those involving lead(IV).

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