Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 1. Preparation of aliphatic and terminal alkynes

R Alan Aitken, J I ATHERTON

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63 Citations (Scopus)

Abstract

Thermal extrusion of Ph(3)PO from beta-oxoalkylidenetriphenylphosphoranes 4 to give the alkynes 5, which under conventional pyrolysis conditions is restricted to cases in which R(1) is an electron withdrawing group, has been successfully achieved for R(1) = H or alkyl by using FVP. The method allows convenient construction of multigram quantities of the alkynes 5 from alkyl halides 1 and acid chlorides 3 in three steps with good overall yields. Under the conditions used the ylides with R(2) = cyclobutyl also undergo loss of ethene to provide convenient access to the vinylalkynes 6.

Original languageEnglish
Pages (from-to)1281-1284
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number10
DOIs
Publication statusPublished - 21 May 1994

Keywords

  • ELEMENTO-ORGANIC COMPOUNDS
  • CONVENIENT SYNTHESIS
  • 6TH GROUPS
  • ACETYLENES
  • 5TH

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