Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 2. Two-step conversion of acid chlorides into acetylenic esters and terminal alkynes

R Alan Aitken, C E R HORSBURGH, J G MCCREADIE, S SETH

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

The known thermal extrusion of Ph(3)PO from alpha-acyl-alpha-ethoxycarbonyl ylides 1 to give acetylenic esters 2 can be accomplished in excellent yield by using flash vacuum pyrolysis (FVP) at 500 degrees C. Upon raising the furnace temperature to 750 degrees C, this reaction is accompanied by the unexpected loss of the ethoxycarbonyl group to give the terminal alkynes 7 in moderate yield. A mechanism is proposed for this reaction based on isotopic labelling studies. Ten new examples of ylides 1 have been prepared for the first time.

Original languageEnglish
Pages (from-to)1727-1732
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number13
DOIs
Publication statusPublished - 7 Jul 1994

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