The synthesis and characterization of 4-isopropylanilino derivatives of cyclotriphosphazene

Abstract

Hexachlorocyclotriphosphazene N3P3Cl6 and gem-disubstituted cyclotriphosphazene derivatives N3P3-Cl4X2 (X = Ph, PhS, PhNH) were reacted with 4-isopropylaniline to give geminal tetra and hexa substituted compounds (1a-4a, 1b-4b). The compounds (1a-4a, 1b-4b) were separated by column chromatography on silica gel and analyzed by elemental analysis, mass spectrometry, and P-31 and H-1 NMR spectroscopies, and also crystal structures of 2a and 3b were determined by X-ray crystallography. Compounds were prepared to cover the normal ranges of C-, S- and N-substituents in cyclophosphazene (X = Cl, Ph, SPh, NHPh). Compounds (1a-4a, 1b-4b) were reported for the first time. We additionally investigated the effect of substituent (Cl, Ph, SPh, NHPh) on P-31 NMR chemical shifts of neighboring phosphorus atoms. (C) 2013 Elsevier B.V. All rights reserved.