Formation of Unexpected Heterocyclic Products from Pyrolysis of Thiocarbonyl Stabilised Phosphonium Ylides

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

Research output: Contribution to journalArticle

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
JournalHeterocycles
Volume88
Issue number2
Early online date14 Aug 2014
DOIs
Publication statusPublished - 2014

Fingerprint Dive into the research topics of 'Formation of Unexpected Heterocyclic Products from Pyrolysis of Thiocarbonyl Stabilised Phosphonium Ylides'. Together they form a unique fingerprint.

  • Cite this