Phosphonitrilic Compounds. V. Cyclized Products from the Reactions of Hexachlorocyclotriphosphazene (Phosphonitrilic Chloride Trimer) with Aromatic Dihydroxy, Dithiol, and Diamino Compounds

Hexachlorocyclotriphosphazene, (NPCl₂)₃, reacted with 2,3-dihydroxynaphthalene, with 2,2ʹ-dihydroxybiphenyI, with toluene-3,4-dithiol, and with o-phenylenediamine, in the presence of base, to yield, respectively, tris(naphthyl-2,3-dioxy)-cyclotriphosphazene, tris(diphenyl-2,2ʹ-dioxj-)cyClotriphosphazene, tris(l-methylphenyl-3,4-dithio)cyclotriphosphazene, and tris(o-phenylenediamino)cyclotriphosphazene. When the reactant stoichiometry for the o-phenylenediamine reaction was changed, 1,1-o-phenylenediamino-3,3,5,5-tetrachlorocyclotriphosphazene was also obtained. The products were characterized by analytical, infrared, ultraviolet, and nmr methods, and the polymerization, inclusion, and polarographic behavior of specific compounds were examined. No evidence was found for interaction of the -π electrons of the cyclophosphazene system with the lone-pair or π electrons of the side groups.