Thermal rearrangement of thiocarbonyl-stabilised triphenylphosphonium ylides leading to (Z)-1-diphenylphosphino-2-phenylsulfenylalkenes

Chem Commun (Camb). 2009 Dec 21:(47):7381-3. doi: 10.1039/b913107h. Epub 2009 Nov 5.

Abstract

While thermolysis of thiocarbonyl-stabilised phosphonium ylides generally results in extrusion of Ph(3)PS to give alkynes, those with a P=CH function instead undergo a novel P to S transfer of a phenyl group to give (Z)-configured 1-phosphino-2-sulfenylalkenes of interest as bidentate ligands.

MeSH terms

  • Alkynes / chemical synthesis*
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Organophosphorus Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry*
  • Sulfur Compounds / chemical synthesis*
  • Temperature

Substances

  • Alkynes
  • Organophosphorus Compounds
  • Sulfhydryl Compounds
  • Sulfur Compounds