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

The nucleophilic substitution reaction of hexachlorocyclotriphosphazene (N 3 " role="presentation"> 3 3 _{3} P 3 " role="presentation"> 3 3 _{3} Cl 6 " role="presentation"> 6 6 _{6} , trimer) ( 1 ) with 4-hydroxy-1-naphthaldehyde ( 2 ) has been investigated for the first time. 4 ′ " role="presentation"> ′ ′ ^{{\prime}} -Oxy-1 ′ " role="presentation"> ′ ′ ^{{\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 Cs 2 " role="presentation"> 2 2 _{2} CO 3 " role="presentation"> 3 3 _{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 K 2 " role="presentation"> 2 2 _{2} CO 3 " role="presentation"> 3 3 _{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 ( 1 " role="presentation"> 1 1 ^{1} H and 31 " role="presentation"> 31 31 ^{31} P) spectroscopies.