Issue 17, 1994
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 4. Stepwise construction of terminal 1, 3-diynes, conjugated diacetylenic esters and a triacetylenic ester

R. Alan Aitken  and  Shirley Seth  

Abstract

Thirteen examples of stabilised alkynoyl ylides 6 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 500 °C, to undergo extrusion of Ph3PO to give the diacetylenic esters 7 in moderate yield. At 750 °C the same ylides afforded terminal 1, 3-diynes 8 although often in poor yield. For R = 2-MeSC6H4 both 7 and 8 undergo secondary loss of Me˙ and cyclisation to give 2-alkynylbenzothiophene derivatives 9 and 10 in low yield. The first example of an alkadiynoyl ylide 11 has been prepared and is converted by FVP at 500 °C into the triacetylenic ester 12.

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Article information

DOI
https://doi.org/10.1039/P19940002461
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 2461-2466

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Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 4. Stepwise construction of terminal 1, 3-diynes, conjugated diacetylenic esters and a triacetylenic ester

R. A. Aitken and S. Seth, J. Chem. Soc., Perkin Trans. 1, 1994, 2461 DOI: 10.1039/P19940002461

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