Synthesis, thermal reactivity, and kinetics of stabilized phosphorus ylides, part 2: [(Arylcarbamoyl)(cyano)-methylene]triphenylphosphoranes and their thiocarbamoyl analogues

R. Alan Aitken, Nouria A. Al-Awadi, Osman M. E. El-Dusouqui, Dorcas M. M. Farrell, Ajith Kumar

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

A series of five cyano(arylcarbamoyl) phosphorus ylides 2 and five cyano(arylthiocarbamoyl) phosphorus ylides 3 are prepared and fully characterized. Pyrolytic reaction products of a representative example of each type obtained by flash vacuum pyrolysis technique show that they undergo thermal extrusion of Ph3PO or Ph3PS. Kinetic study of the gas-phase pyrolysis of each ylide by static method shows that these reactions are unimolecular and first order with no significant substituent effect, but the thiocarbamoyl ylides 3 react 40-65 times more rapidly than their carbamoyl analogues 2. (c) 2006 Wiley Periodicals, Inc.

Original languageEnglish
Pages (from-to)496-502
Number of pages7
JournalInternational Journal of Chemical Kinetics
Volume38
DOIs
Publication statusPublished - Aug 2006

Keywords

  • FLASH VACUUM PYROLYSIS
  • GAS-PHASE ELIMINATION
  • GAMMA-AMINO ACID
  • CARBOXYLIC-ACIDS
  • TERMINAL ALKYNES
  • WITTIG REAGENTS
  • ESTERS
  • ISOTHIOCYANATES
  • ISOCYANATES
  • DERIVATIVES

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