Intermediates in the Peroxy Acid Oxidation of Phenyl Phenylmethanethiosulfinate

Article abstract of DOI:10.1021/jo00333a011

The m-chloroperoxybenzoic acid (MCPBA) oxidation of phenyl phenylmethanethiosulfinate (9) in CDCl3 has been studied.Low-temperature 1H NMR and 13C NMR spectra show that phenyl phenylmethanethiosulfonate (7), phenylmethanesulfonic acid (26), and phenylmethanesulfinic acid (27) are formed during the early stages of oxidation.Although 7 may be formed via direct attack of MCPBA at the sulfinyl sulfur atom of 9, the presence of 7, 26, and 27 is also explicable in terms of formation and rearrangement of metastable α-disulfoxide (13) and sulfenyl sulfinate (14) intermediates.