Monosodium acetonitriles, their preparation, properties and reactions

Abstract

Monosodium acetonitrile and homologous compounds are prepared by the reaction of sodium bis(trimethylsilyl)amide with acetonitrile or the corresponding nitriles in either solution at low temperature. The IR and NMR spectra of these compounds are discussed. Sodium acetonitrile adds to polar double bonds (carbonyl and cyano groups) only. It is shown that sodium acetonitrile and analogous compounds are the intermediates in the condensation reactions of nitriles to enamines. Sodium acetonitrile acts as carbene generator, preferably in the presence of cyanide acceptors.