Substituent Exchange and Carbon-Oxygen Bond Cleavage with Aryloxycyclophosphazenes

H. R. Allcock, L. A. Smeltz

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21 Scopus citations

Abstract

Aryloxycyclotriphosphazenes, [NP(OAr)2]3, such as I-IV, undergo substituent exchange reactions with organic nucleophiles. This constitutes a route for the preparation of mixed substituent organophosphazenes, some of which are inaccessible by other methods. The ease of displacement of OAr in [NP(OAr)2]3 by CF3CH2O- decreased with OAr in the order, OC6H4NO2-o or -p > OC6H5Cl-p ≫ OC6H5. When OAr was OC6H4NO2-o or -p, ligand exchange was either accompanied by or replaced by nucleophilic attack at the α-carbon of the aromatic residue. This effect was significant when the attacking nucleophile was C6H5O- or C6H5S-, and it predominated when the nucleophile was C6H5NH- or an uncharged primary or secondary amine. The mechanisms of these reactions are discussed.

Original languageEnglish (US)
Pages (from-to)4143-4149
Number of pages7
JournalJournal of the American Chemical Society
Volume98
Issue number14
DOIs
StatePublished - Jul 1 1976

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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