Direct Synthesis of Functionalized Unsymmetrical β-Sulfonamido Disulfides by Tetrathiomolybdate Mediated Aziridine Ring-Opening Reactions

Direct synthesis of unsymmetrical β-sulfonamido disulfides by ring-opening of aziridines by using benzyltriethyl-ammonium tetrathiomolybdate 1 as a sulfur transfer reagent in the presence of symmetrical disulfides as thiol equivalents has been reported. Reaction of benzyl and alkyl disulfides gave unsymmetrical β-sulfonamido disulfides as the only product in very good yields. From the study, it has been observed that aryl disulfides containing p-NO2, p-Cl, and p-CN led to the formation of the corresponding β-aminosulfides as the exclusive products. However, unsubstituted aryl disulfides and the one containing electron-donating substituents (p-Me) provide a mixture of β-sulfonamido mono- and disulfides as the products.