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

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Pyrolysis
Thiones
Phenylalanine
Alanine
Phosphorus
Salts

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Aitken, R. Alan ; Barker, Graeme ; Cleghorn, Lee P. ; Reid, Euan J. ; Roberts, Sheryl S. / Formation of Unexpected Heterocyclic Products from Pyrolysis of Thiocarbonyl Stabilised Phosphonium Ylides. In: Heterocycles. 2014 ; Vol. 88, No. 2. pp. 1135-1147.
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Formation of Unexpected Heterocyclic Products from Pyrolysis of Thiocarbonyl Stabilised Phosphonium Ylides. / Aitken, R. Alan; Barker, Graeme; Cleghorn, Lee P.; Reid, Euan J.; Roberts, Sheryl S.

In: Heterocycles, Vol. 88, No. 2, 2014, p. 1135-1147.

Research output: Contribution to journalArticle

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AU - Roberts, Sheryl S.

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AB - 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.

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