Synthesis and decarboxylative Wittig reaction of difluoromethylene phosphobetaine

Chem Commun (Camb). 2013 Sep 4;49(68):7513-5. doi: 10.1039/c3cc44271c.

Abstract

A key intermediate, difluoromethylene phosphobetaine, in the Wittig reaction of ClCF2CO2Na-Ph3P with aldehydes was synthesized and characterized, which confirmed the reaction mechanism. The decarboxylation of this stable intermediate was a convenient approach for Wittig difluroolefination. Its reactivity could be adjusted by the modification of the substituent on the phosphorus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemical synthesis*
  • Acetates / chemistry*
  • Aldehydes / chemistry*
  • Decarboxylation
  • Models, Molecular
  • Molecular Structure
  • Organophosphates / chemistry*
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry*

Substances

  • Acetates
  • Aldehydes
  • Organophosphates
  • Organophosphorus Compounds
  • chlorodifluoroacetic acid
  • triphenyl phosphate