Syntheses and characterizations of cyclotriphosphazenes containing a 4-oxy-1-naphthaldehyde group

Abstract

The nucleophilic substitution reaction of hexachlorocyclotriphosphazene (N33_{3}P33_{3}Cl66_{6}, trimer) (1) with 4-hydroxy-1-naphthaldehyde (2) has been investigated for the first time. 4′′^{{\prime}} -Oxy-1′′^{{\prime}} -naphthaldehyde substituted mono- (3), bis- (4), and tris- (5) cyclotriphosphazenes were obtained from the nucleophilic substitution of compound 1 with 2 in a 1:2 molar ratio in the presence of Cs22_{2}CO33_{3} in acetone at reflux. The pentakis-(6) and hexakis-substituted (7) cyclotriphosphazenes were prepared from the reaction of 1 with 2 in a 1:7 molar ratio using K22_{2}CO33_{3} as a proton abstractor in tetrahydrofuran at room temperature. The structures of the new compounds (3-7) were determined by elemental analysis, FT-IR, and mass and nuclear magnetic resonance (11^{1}H and 3131^{31}P) spectroscopies.