The synthesis of oxime group bearing cyclotriphosphazenes and their deivatives

In this study, hexachlorocylotriphosphazene (1) was reacted with biphenyl-2,2?-diol. From this reaction, 2,2-dichloro-4,4,6,6-bis[spiro(2?,2??-dioksi-1?,1??-biphenylyl)]cyclotriphosphazene (2) was obtained. Since hexachlorocyclotriphosphazene is sensitive to air and moisture, experimental studies were carried out at without air and moisture in argon atmosphere. 2,2-Bis(4-acetylphenoxy)- 4,4,6,6-bis[spiro(2?,2??-dioksi-1?,1??-biphenylyl)]cyclotriphosphazene (3) was synthesized from the reaction of 2 with 4-hydroxyasetophenon. 2,2-Bis(4-[(1)-N-hydroxyethanimidoyl] phenoxy)-4,4,6,6- bis[spiro(2?,2??-dioksi-1?,1??-biphenylyl)]cyclotriphosphazene (4) was synthesized from the reaction of 3 with hydroxlaminehydrochloride in pyridine. Compound 4 was reacted with, chloroacetyl chloride, benzoyl chloride, propanoyl chloride, methyl iodide, 2-bromoethanol, 4-methoxybenzoyl chloride, acetyl chloride, benzyl chloride and 2- chlorobenzoyl chloride. The structure of the compounds were defined by elemental analysis, IR, 1H, 13C and 31P-NMR spectroscopy. Disubstituted compounds were obtained from the reactions of 4 with benzoyl chloride, methyl iodide, acetyl chloride, benzyl chloride and 4-methoxybenzoyl chloride via all of the oxime protons replacement with alkyl or aryl groups. Pure and defined products could not be obtained from the reaction of 4 with propanoyl chloride, 2-bromoethanol, chloroacetyl chloride and 2- chlorobenzoyl chloride. KEYWORDS: Hexachlorocyclotriphosphazene, phosphazene, cyclophosphazene, oxime, oxime-phosphazenes.