Synthesis, thermal reactivity and kinetics of substituted [(benzoyl) (phenylcarbamoyl)methylene]triphenylphosphoranes and their thiocarbamoyl analogues

Robert Alan Aitken, NA Al-Awadi, Graham Dawson, O El-Dusouqi, DMM Farrell, K Kaul, A Kumar

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

A range of 16 substituted benzoyl/arylcarbamoyl and benzoyl/arylthiocarbamoyl stabilised ylides have been prepared. They are found under conditions of flash vacuum pyrolysis to fragment giving a benzoyl ylide and aryl isocyanate or isothiocyanate accompanied in some cases by secondary pyrolysis products. Kinetic studies show the thiocarbamoyl ylides to react consistently faster than their carbamoyl analogues and substituent effects suggest a polar cyclic transition state, which involves attack by the benzoyl oxygen on the carbamoyl/thiocarbamoyl NH. (C) 2004 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)129-135
Number of pages7
JournalTetrahedron
Volume61
DOIs
Publication statusPublished - 3 Jan 2005

Keywords

  • ylides
  • pyrolysis
  • kinetics
  • substituent effects
  • STABILIZED PHOSPHORUS YLIDES
  • PHASE PYROLYTIC REACTIONS
  • FLASH VACUUM PYROLYSIS
  • WITTIG REAGENTS
  • ISOTHIOCYANATES
  • ISOCYANATES
  • BEHAVIOR

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