Synthesis and characterization of the first geminal dibenzylaminocyclotriphosphazene derivatives

Abstract

In this paper, the reactions of dibenzylamine with selected mono-spiro and geminal di-substituted cyclotriphosphazene derivatives, N3P3Cl4R2 [R-2 = (OCH2(CF2)(2)CH2O) (1a); SPh (1b); NHPh (1c); (OCH2CH2CH2NH) (1d) and NHBut (1e)] were systematically studied. The influence of the electron-supplying properties of the PR2 groups on the reaction pathway and degree of substitution of the product was investigated. The aminolysis reactions of N3P(3)Cl(4)[NH(CH2)(3)O] and N3P3Cl4[NHBut](2) with dibenzlyamine led to formation of bis geminal dibenzylamino derivatives (4d and 4e). The reaction of N3P3Cl4[NHPh](2) was carried out with dibenzylamine at the same mole ratio, leading to the fully substituted product (5c) where four chloride atoms replaced with dibenzylamino groups. The first examples of geminal dibenzylamino cyclotriphosphazene compounds (4d, 4e and 5c) were obtained.