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

doi:10.1039/p19940001727

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

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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 language	English
Pages (from-to)	1727-1732
Number of pages	6
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	13
DOIs	https://doi.org/10.1039/p19940001727
Publication status	Published - 7 Jul 1994

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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.",

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AU - MCCREADIE, J G

AU - SETH, S

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

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