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Paper | Special issue | Vol 88, No. 2, 2014, pp.1135-1147
Published online, 14th August, 2013
DOI: 10.3987/COM-13-S(S)70
Formation of Unexpected Heterocyclic Products from Pyrolysis of Thiocarbonyl Stabilised Phosphonium Ylides

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

*School of Chemistry, University of St. Andrews, North Haugh, St Andrews, Fife KY 16 9ST, U.K.

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.