Synthesis and characterization of alkyl- and acyl-substituted oxime-phosphazenes


ÇİL E., ARSLAN M. , GÖRGÜLÜ A. O.

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, vol.83, no.12, pp.2039-2045, 2005 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 83 Issue: 12
  • Publication Date: 2005
  • Doi Number: 10.1139/v05-223
  • Journal Name: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.2039-2045

Abstract

Two oxime-cyclophosphazenes were prepared from the hexakis(4-formylphenoxy)cyclotriphosphazene (2) and hexakis(4-acetylphenoxy)cyclotriphosphazene (8). The reactions of these oximes with ethyl bromide, allyl bromide, propanoyl chloride, and acriloyl chloride were studied. Hexasubstituted compounds were obtained from the reactions of hexakis{4-[(hydroxyimino)methyl]phenoxy}cyclotriphosphazene (3) with ethyl bromide (4), allyl bromide (5), and propanoyl chloride (6), however, the oxime groups on 3 rearranged to nitrile (7) in the reaction of 3 with acriloyl chloride. Hexasubstituted compounds were also obtained from the reactions of hexakis{4-[(1)-N-hydroxyethaneimidoyl]phenoxy}cyclotriphosphazene (9) with allyl bromide (11) and propanoyl chloride (12). Tetra- and penta-substituted products were obtained from the reactions of 9 with ethyl bromide (10) and acriloyl chloride (13), respectively. All products were generally obtained in high yields. The structures of the compounds were defined by elemental analysis, IR, H-1, C-13, and P-31 NMR spectroscopy.