α-Iminotrifluoroethylphosphonates: The First Representatives of N-H Imidoyl Phosphonates

Abstract

A convenient synthetic approach to previously unknown N-H imidoyl phosphonates, based on addition of dialkyl phosphites to trifluoroacetonitrile, has been developed. The synthetic potential of such imines, which exist as equilibrium mixtures of E/Z-isomers, was demonstrated by their easy reduction and functionalization with O- and P-centered nucleophiles, to afford derivatives of α-aminophosphonic acids containing a trifluoromethyl group. Furthermore, interaction with mercaptoacetic acid proceeds with intramolecular cyclization of the intermediate adduct to produce a novel 2-phosphorylated N-H thiazolidone. Interaction between the N-H imines and trichloroacetylisocyanate leads to novel, reactive, phosphorylated N-acylated imines.

Key words

imidoyl phosphonates - N-H imines - trifluoromethyl - aminophosphonates - E/Z-isomerism

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