Formation of N-mono- and NN-di-benzoyl amines by benzoylation of phosphoramidate and related anions

Abstract

Phosphoramidate and phosphinic amide anions react with benzoyl chloride and with benzoic anhydride to give N-mono- and NN-di-benzoyl amines. In contrast, the known diethyl N-acetyl-N-phenylphosphoramidate can be obtained by treatment of diethyl N-phenylphosphoramidate anion with acetyl chloride. Possible mechanisms for these reactions are discussed; the most likely involves a pentaco-ordinate intermediate reacting intra- or intermolecularly with more acylating agent or protic solvent.