The reactions of cyclotriphosphazene with 2-(2-hydroxyethylamino)ethanol. Spectroscopic studies of the derived products

Abstract

The reactions of cyclotriphosphazene (1) with 2-(2-hydroxyethylamino)-ethanol (2) were investigated. 2-(2-hydroxyethylamino)-ethanol (2) is a tri-functional reagent consisting of both aliphatic hydroxyl and the secondary amino groups and its nucleophilic substitution reactions with cylotriphosphazene can lead to different product types; open chain, spiro, ansa, bridged and their mixtures. The reactions with one, two and three equimolar ratios of 2-(2-hydroxyethylamino)-ethanol, in the presence of NaH at 0-10 degrees C and at room temperature gave the following cyclotriphosphazene derivatives: one mono-spiro, N3P3Cl4[O-(CH2)(2)-NH-(CH2)(2)-O] (3, 1:1, r.t.); its isomer mono-ansa (5, 1:1, r.t.); one dispiro, N3P3Cl2[O-(CH2)(2)-NH-(CH2)(2)-O](2) (4, 1:1, r.t.); its isomer spiro-ansa (6, 1:2, r.t.); and one single-bridged compound with spiro substituted units, N3P3Cl3[O-(CH2)(2)-NH-(CH2)(2)-O](3)N3P3Cl3 (7, 1:3, at 0-10 degrees C); as well as single-, N3P3Cl5[O-(CH2)(2)-NH-(CH2)(2)-O]N3P3Cl5 (8, 1:2, r.t.), double-, N3P3Cl4[O-(CH2)(2)-NH-(CH2)(2)-O](2)N3P3Cl4 (9, 1:2, r.t.), and tri-bridged, N3P3Cl3[O-(CH2)(2)-NH-(CH2)(2)-O](3)N3P3Cl3 (10, 1:3, at 0-10 degrees C) derivatives. Triple-bridged derivative is the major product in this system. The structures of the novel-derived compounds were characterized by TLC-MS, FT-IR, elemental analysis, H-1, and P-31 NMR spectral.