Oxidative triflamidation of allyl cyanide in nitrile solutions

Abstract

The reaction of triflamide with allyl cyanide in benzonitrile and isobutyronitrile solutions in the presence of NBS has been studied. In both cases, the corresponding amidines - the products of the solvent incorporation are formed. In benzonitrile, depending on the reaction conditions, the isomeric N -(2-bromo-3-cyanopropyl)- N '-(triflyl)benzamidine and N -(1-bromo-3-cyanoprop-2-yl)- N '-(triflyl)benzamidine were obtained in various ratio. From the reaction in isobutyronitrile, N -(2-bromo-3-cyanopropyl)- N '-(triflyl)isobutyramidine and the product of diamination, N -[3-cyano-1-(triflamido)propyl]isobutyramide were isolated.