Nucleophilic substitution reactions of monofunctional nucleophilic reagents with cyclotriphosphazenes containing 2,2-dioxybiphenyl units

Abstract

The nucleophilic substitution reactions of mono-and bis-spiro-2,2 ′-dioxybiphenyl cyclotriphosphazenes (3 and 4) with cyclopropanemethylamine (5) and aniline (6) were performed in the presence of trimethylamine in THF. Five novel cyclopropanemethylamino-and anilino-substituted spiro-2,2 ′-dioxybiphenyl cyclotriphosphazene derivatives (7-11) were obtained from these reactions. The molecular structures of the new cyclotriphosphazene derivatives (7-11) were characterized by elemental analysis, MALDI-TOF MS, FT-IR, and NMR (31 P and 1 H) spectroscopies. The structure of the spiro-(2,2 ′-dioxybiphenyl)-bis-(anilino)-cyclotriphosphazene (11) was also determined by single-crystal X-ray crystallography.