Syntheses of Polymeric Azasulfonium Salts and Iminosulfuranes

Polymeric azasulfonium salts were synthesized by the reaction of sulfide polymers with such N-halo compounds as N-chloroacetamide, N-bromoacetamide, and ethyl N-chlorocarbamate. These polymers are soluble in CH 2 CI 2 , CHCl 3 , DMSO, and DMF, but insoluble in benzene, acetone, and water. The treatment of these polymeric azasulfonium salts with triethylamine afforded polymers containing the iminosulfurane structure in high yields. On the other hand, these iminosulfurane polymers were also synthesized by the reaction of sulfide polymers with nitrene which was generated from the photolysis of ethyl azidoformate.