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


Çil E., Arslan M., GÖRGÜLÜ A. O.

Heteroatom Chemistry, cilt.17, sa.2, ss.112-117, 2006 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 17 Sayı: 2
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1002/hc.20176
  • Dergi Adı: Heteroatom Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.112-117
  • Marmara Üniversitesi Adresli: Evet

Özet

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, monochloroacetone, 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, tetra-substituted 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.