NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles

Ziad Moussa, Saleh A. Ahmed, Ahmad S. ElDouhaibi, Shaya Y. Al-Raqa

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

NMR Studies on the reaction of triphenylphosphine with various amounts of triflic anhydride at 0 °C is described. The reagent structure resulting from mixing 1.3 equiv of Ph3P with Tf2O (1.0 mmol) has been established as an equilibrium mixture consisting mainly of triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate and the corresponding bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate dimer. The electrophilic properties of the system have been exploited in the development of a mild method for converting aldoximes into nitriles. The dehydration occurs at 0 °C under very mild conditions by initial activation of the oxime oxygen, followed by treatment with a base and subsequent elimination of triphenylphosphine oxide. The substrate scope and functional group tolerance of this useful method are explored.

Original languageEnglish
Pages (from-to)1826-1831
Number of pages6
JournalTetrahedron Letters
Volume51
Issue number14
DOIs
Publication statusPublished - Apr 7 2010
Externally publishedYes

Keywords

  • Aldoximes
  • Bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate
  • Dehydration
  • Nitriles
  • Triflic anhydride
  • Triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate
  • Triphenylphosphine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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