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

Yuliya V. Rassukana; Mykola V. Kolotylo; Oleksii A. Sinitsa; Volodymir V. Pirozhenko; Petro P. Onys’ko

doi:10.1055/s-2007-983838

PAPER

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

Yuliya V. Rassukana, Mykola V. Kolotylo, Oleksii A. Sinitsa, Volodymir V. Pirozhenko, Petro P. Onys’ko*
Institute of Organic Chemistry, National Academy of Sciences, 5 Murmanskya St, 02094 Kiev, Ukraine
Fax: +38(44)5732643; e-Mail: onysko@rambler.ru;

Abstract

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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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Referenzen

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