Oxidation of alkyl and aryl iodides, phenylacetaldehyde and alkenes by dimethyldioxirane. Reaction products and mechanism

Alkyl and aryl iodides are smoothly oxidized to iodosoderivatives and phenylacetaldehyde is oxidized to phenylacetic acid or benzyl acetate by dimethyldioxirane depending on the presence or not of oxygen. These results and the epoxidation or the allylic oxidation of alkenes by the same reagent are explained by a general free-radical mechanism.