Isomerization of β-halo disulfides (alkyl 2-haloethyl disulfides)

The methyl ester, amide, dimethylamide, and anilide of -methylthioglycidic acid are readily cleaved by methane and acetylsulfenyl chlorides to give mixtures of the corresponding isomeric cleavage products — vicinal chlorodithio derivatives of isobutyric acid. It is shown that the ratio of isomers obtained depends both on the character of the substituent in the carboxyl group of the isobutyric acid and on the character of the substituent attached to the sulfur atom in the sulfenyl chloride (sulfomonochloride) used. It was found that -halo disulfides, like -halo sulfides, are capable of isomerization.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 8–12, January, 1973.