Preparation of vinyl allenes from 1-lithio-1,3-dienyl phosphine oxides and aldehydes by the Wittig-Horner reaction

J Org Chem. 2005 Oct 28;70(22):8785-9. doi: 10.1021/jo051178c.

Abstract

[reaction: see text] Vinyl allenes were prepared in high yields by the Wittig-Horner reaction of 1-lithio-1,3-dienyl phosphine oxides with aldehydes. 1-Lithio-1,3-dienyl phosphine oxides were generated in situ from lithiation of 1-iodo-1,3-dienyl phosphine oxides, which were obtained by iodination of alpha-phosphinozirconacyclopentadienes. As a whole, a vinyl allene is synthesized from two different alkynes and one aldehyde.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkadienes / chemical synthesis
  • Alkadienes / chemistry*
  • Iodine / chemistry
  • Lithium Compounds / chemistry*
  • Molecular Structure
  • Oxides / chemistry*
  • Phosphines / chemistry

Substances

  • Aldehydes
  • Alkadienes
  • Lithium Compounds
  • Oxides
  • Phosphines
  • propadiene
  • Iodine
  • phosphine