Reaction of N-Phenyltrifluoromethanesulfonamide with Carbodiimides

Abstract

N-Phenyltrifluoromemanesulfonamide reacted with N,N′-dicyclohexylcarbodiimide in methylene chloride to give exchange products, N-cyclohexyltrifluoromethanesulfonamide and N-cyclohexyl-N′-phenylcarbodiimide. Reaction of the latter with trifluoromethanesulfonamide afforded N-cyclohexyl-N′-phenyl-N″-(trifluoromethanesulfonyl)guanidine. In the reaction of N-phenyltrifluoromethanesulfonamide with N,N′-dicyclohexylcarbodiimide in acetonitrile, substituent exchange was a minor process, whereas the major one was dimerization of N,N′-dicyclohexylcarbodiimide catalyzed by N-phenyltrifluoromethanesulfonamide as NH acid.