Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 12. Extrusion of Ph3P from sulfonyl ylides and reactivity of the resulting sulfonyl carbenes

Robert Alan Aitken, MJ Drysdale, G Ferguson, AJ Lough

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23 Citations (Scopus)

Abstract

Twelve sulfonyl stabilised phosphorus ylides have been prepared and their behaviour upon flash vacuum pyrolysis at 600 degrees C has been examined. Examples with an arylsulfonyl substituent undergo loss of Ph3PO to give intractable products but those with an arylmethylsulfonyl substituent separately lose Ph3P and SO2 to give products consistent with the intermediacy of sulfonyl carbenes. X-Ray structure determinations of one ylide from each series show a more significant P-O non-bonding interaction in the first case, providing some explanation for the different thermal reactivity.

Original languageEnglish
Pages (from-to)875-880
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number5
DOIs
Publication statusPublished - 7 Mar 1998

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