Synthesis of oxime bearing cyclophosphazenes and their reactions with alkyl and acyl halides

Abstract

Two novel cyclophosphazenes containing oxime groups were prepared from the hexakis(4-formylphenoxy)cyclotriphosphazene (2) and hexakis-(4-acetylphenoxy)cyclotriphosphazene (7). The reactions of these oximes with acetyl chloride, chloroacetyl chloride, methyl iodide, propyl chloride, mono- chloroacetone, and 1,4-dichlorobutane were studied. Hexasubstituted compounds were obtained from the reactions of hexakis(4-[(hydroxyimino)methyl]phenoxy)cyclotriphosphazene (3) with acetyl chloride (4) and chloroacetyl chloride (5); however, tetrasubstituted product was obtained from methyl iodide (6). Tetra- and trisubstituted products were obtained from the reactions of hexakis(4-[(1)-N-hydroxyethaneimidoyl]phenoxy)cyclotriphosphazene (8) with acetyl chloride (9) and chloroacetyl chloride (10), respectively. All products were obtained in high yields. Pure and defined product could not be obtained from the reaction of 8 with methyl iodide, and could not be also obtained from the reactions of 3 and 8 with propyl chloride, monochloroacetone, and 1,4-dichlorobuthane. The structures of the compounds were defined by elemental analysis, IR, 1H, 13C, and 31P NMR spectroscopy. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:112–117, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20176