Desulfurative Acetoxylation of Alkyl Benzyl Phenyl Sulfides

The reaction of thiophenylsulfides with diacetoxyiodobenzene, iodine and light produced corresponding acetoxylated products, allowing the formation of new C-O bonds from starting materials other than carbonyls in high yields. Hence, under these conditions, thiophenylsulfide underwent displacement/substitution by an acetate. 1H-NMR studies of the reaction carried out with exclusion of each single reactant pointed at two operative pathways and to the involvement of an intermediate that was assigned as an acetoxy sulfonium (IV) species.