Interconversion of unsaturated C4 nitriles under basic conditions I. An IR-UV—VIS spectroscopic study in the presence of butyllithium Original Research Article

The interconversion of isomeric unsaturated C4 nitriles (allyl cyanide, crotononitrile and methacrylonitrile) in solution in the presence of butyllithium was investigated by means of FTIR and UV—VIS spectroscopy. The generation and existence of a carbonionic intermediate in the base-induced interconversion of C4 nitriles were unequivocally proven and characterized by the shifts in the v(CN) and v(CC) vibration regions of the IR spectra and in the UV-VIS spectra of the reacting nitriles.