Oxidation & 1, 5-hydride shift of sulfoximine derivatives

Abstract

[ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI AT REQUEST OF AUTHOR.] Oxidation of N-alkyl and N-aryl sulfoximines and 1,5-hydride shift of S-alkenyl sulfoximines have been studied. Oxidation of N-alkyl sulfoximines using dimethyldioxirane gave sulfones and nitroso derivatives. A mechanism for the process was proposed. Thermal isomerization and decomposition of different N-substituted and S-alkenyl sulfoximines was studied. Cyclic sulfoximines and N-H sulfoximines were obtained. Reactivity was compared. Stereocenters and isomerization of cyclic products were studied. 1,5-Hydride shift was proposed as the mechanism for these transformations.