Formation of unexpected heterocyclic products from pyrolysis of thiocarbonyl stabilised phosphonium ylides

R Alan Aitken, Graeme Barker, Lee Paul Cleghorn, Euan J. Reid, Sheryl S. Roberts

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Chiral phthalimido thioxo-stabilised phosphonium ylides, prepared starting from (S)-alanine and (S)-phenylalanine, undergo intramolecular Wittig reaction upon pyrolysis leading to the previously unknown pyrrolo[2,1-a]isoindol-5-one-2-thiones, rather than the expected P to S migration of a phenyl group. Pyrolysis of thioxo-stabilised ylides with three different groups on phosphorus gave some evidence of the required migration, but led in one case to unexpected formation of a 1,4-benzoxaphosphininium salt
Original languageEnglish
Pages (from-to)1135-1147
Number of pages13
JournalHeterocycles
Volume88
Issue number2
Early online date14 Aug 2013
DOIs
Publication statusPublished - Jan 2014

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