Oxidation of cyclic hydrocarbons by cobalt(III) acetate

The oxidation of cyclic alkanes and alkenes by cobalt(III) acetate leads to the formation of cycloalkyl and cycloalkenyl acetates. The formation of chlorinated hydrocarbons is observed for cycloalkanes in the presence of carbon tetrachloride but no incorporation of chlorine takes place in the olefins. The results are best interpreted by assuming a determining role by both steric and conformational effects on the reaction, involving the conversion of a co-ordinated radical to a carbocation.