Oxidative addition of trifluoromethanesulfonamide to vinylcyclohexane and p-chlorostyrene

Abstract

Trifluoromethanesulfonamide reacted with vinylcyclohexane in the system t-BuOCl-NaI to give a mixture of 2,6-dicyclohexyl-1,4-bis(trifluoromethylsulfonyl)piperazine and 2-iodo-1-cyclohexylethanol. Conformational behavior of the heterocyclization product was studied by dynamic NMR. The reaction of p-chlorostyrene with trifluoromethanesulfonamide under analogous conditions produced the corresponding bis-adduct, N-[2-(4-chlorophenyl)-2-(trifluoromethylsulfonylamino)ethyl]trifluoromethanesulfonamide and 1-(4-chlorophenyl)-2-iodoethanol. A probable reaction mechanism was proposed, which rationalizes difference in the behavior of the examined alkenes.