Direct synthesis of functionalized unsymmetrical beta-sulfonamido disulfides by tetrathiomolybdate mediated aziridine ring-opening reactions.
Direct synthesis of unsymmetrical beta-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 beta-sulfonamido disulfides as the only product in very good yields. From the study, it has been observed that aryl disulfides containing p-NO(2), p-Cl, and p-CN led to the formation of the corresponding beta-aminosulfides as the exclusive products. However, unsubstituted aryl disulfides and the one containing electron-donating substituents (p-Me) provide a mixture of beta-sulfonamido mono- and disulfides as the products.
Sureshkumar
Devarajulu
D
Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, Karnataka, India.
Ganesh
Venkataraman
V
Vidyarini
Ravindran Sasitha
RS
Chandrasekaran
Srinivasan
S
D001388:Aziridines / Q000737:chemistry*; D004220:Disulfides / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*
D001388:Aziridines; D004220:Disulfides; D013449:Sulfonamides; D008982:Molybdenum; C020809:tetrathiomolybdate