Studies on organophosphorus compounds. Part 96. Nucleophilicity of the isocyano carbon atom in diethyl isocyanomethylphosphonate. First generation of a phosphorylated nitrile ylide and new syntheses of pyrrolinephosphonates and pyrrolephosphonates

Abstract

Reactions of acyl chlorides with diethyl isocyanomethylphosphonate afford α-ketoimidoyl chlorides which, when treated with triethylamine, provide a new class of nitrile ylides. These species react in situ with alkenes by a 1,3-dipolar cycloaddition mechanism to give phosphoryl pyrrolines or pyrroles.