Oxidation of Organic Sulfides by Permanganate Ion

Article abstract of DOI:10.1021/jo00018a026

The current literature on the oxidation of sulfides by permanganate contains a suggestion that the reaction mechanism involves an electrophilic oxygen transfer in an S_N2-like mechanism.Contrary to this assumption, it is argued that the experimental facts obtained from a study of the oxidation of (arylthio)acetic acids can more reasonably be accommodated in a mechanism that is initiated by the formation of a coordinate covalent bond utilizing an unshared pair of sulfur electrons and empty manganese d-orbitals.Rearrangement of this intermediate then leads to the formation of sulfoxide and manganate(V) ion.