Selective Oxidation of Unsymmetrical Thiosulfinic S-Esters to the Corresponding Thiosulfonic S-Esters with NaIO4

Article abstract of DOI:10.1246/bcsj.54.1443

Unsymmetrical thiosulfinic S-esters were oxidized with sodium metaperiodate in aqueous media to the corresponding unsymmetrical thiosulfonic S-esters nearly quantitatively.The oxidation was accelerated by addition of a catalytic amount of inorganic and organic acids or halogen.Sulfinic esters were produced competitively along with the thiosulfonic S-esters in the oxidation of thiosulfinic S-esters in aqueous alcohol.However, unsymmetrical disulfides were not oxidized selectively to the corresponding unsymmetrical thiosufonic S-esters but a mixture of the both symmetrical and unsymmetrical thiosulfonic S-esters was obtained.