Phosphonitrilic Compounds. XIV.1 Basic Hydrolysis of Aryloxy- and Spiroarylenedioxycyclophosphazenes

H. R. Allcock, E. J. Walsh

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Abstract

Bis(aryloxy)cyclophosphazenes, [NP(OAr)2]3, and spirocyclic arylenedioxycyclophosphazenes, (NPO2-Ar)3, have been hydrolyzed in basic 25 vol % water in diglyme. For the bis(aryloxy) derivatives, the ease of hydrolytic removal of the first aryloxy group in [NP(OR)2]3 from phosphorus is in the order OR = p-NO2C6H4O– > w-NO2C6H4O– > o-NO2C6H4O– ≫ C6H5O– > p-CH3C6H4O–. For the spirocyclic derivatives, the rate of cleavage of the first aryloxy-phosphorus bond is in the order [NP(O2C6H4-1,2)]3 > [NP(O2C10H6-2,3)]3 ≫ [NP(O2C12H8-2,2′)]3 and [NP(O2C12H6-1,8)]3. The mechanisms of these reactions are discussed, and comparisons are made with related phosphate ester hydrolyses.

Original languageEnglish (US)
Pages (from-to)4538-4545
Number of pages8
JournalJournal of the American Chemical Society
Volume94
Issue number13
DOIs
StatePublished - Jun 1 1972

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All Science Journal Classification (ASJC) codes

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

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