Studies of organophosphorochloridates. Part IV. Synthesis of N-substituted phosphoramidic hydrazides, hydrazones, and azides

Abstract

The preparation of a range of N-substituted phosphoramidohydrazides, hydrazones, and azides is described. NN′-Dibenzylphosphorodiamidic azide is comparatively stable: at 180–200° pyrolysis occurred to give a mixture of products; in boiling decane NN′-dibenzylphosphenimidic amide was formed; the latter also resulted from attempted insertion reactions with boiling o-xylene and piperidine. The azide was unchanged by irradiation with u.v. light, and by boiling ethanol; benzylamine however gave NN′N″-tribenzylphosphoric triamide.

The preparation of arylsulphonyl derivatives of the phosphorodiamidohydrazides by attempted condensation of the hydrazide with the sulphonyl chloride was unsuccessful. A pure product was obtained by treatment of p-toluenesulphonohydrazide with NN′-diphenylphosphorodiamidic chloride. The i.r., n.m.r., and ³¹P-spectral data of these compounds are briefly discussed.