Synthesis and characterization of formyl-bearing and imine-bearing organocyclotriphosphazenes from o-vanillin

In order to obtain organocyclotriphosphazene bearing hexaformyl groups, the reaction of hexachlorocyclotriphosphazene with o-vanillin (2-formyl-6-methoxy-phenol) in acetonitrile and THF solvents, in the presence of K2CO3 and at room conditions was carried out. From these reactions, it was understood that organocyclotriphosphazene bearing hexaformyl groups was not formed. From these reactions, it was determined that the white solid obtained in acetonitrile solvent was a mixture of 2-chloro-2,4,4,6,6-penta(2-formyl-6-methoxy-phenoxy)cyclotriphosphazene (2) and 2,2-dichloro-4,4,6,6-tetra(2-formyl-6-methoxy-phenoxy)cyclotriphosphazene (3). These two compounds could not be purified by chromatographic or any other methods. In the reaction in THF solvent, the pure compound obtained was determined to be 2,2,4-trichloro-4,6,6-tri(2-formyl-6-methoxy-phenoxy)cyclotriphosphazene (4). In order to obtain organocyclotriphosphazenes in which the formyl groups in organocyclotriphosphazene, which is a mixture of compounds 2 and 3, were converted to imine, the reactions were carried out with aniline, some aniline derivatives and aliphatic amines. In all of these reactions, it was determined by FTIR spectrometry during the reaction that not all formyl groups were converted to imine. It was determined that organocyclotriphosphazenes carrying both imine and formyl groups were formed from aniline derivatives carrying electron-withdrawing groups. The structures of the compounds were characterized by FTIR and NMR (1H and 31P).