The sulphenic acid intermediates produced thermally from penicillin S-oxides undergo addition to acetylenic esters to produce conjugated sulphoxides in good yields. These vinylic sulphoxides are subject to nucleophilic addition reactions, with, for example, diethyl sodiomalonate, which proceed in a stereoselective manner. Intramolecular addition reactions have also been observed.
D. H. R. Barton, I. H. Coates, P. G. Sammes and C. M. Cooper, J. Chem. Soc., Perkin Trans. 1, 1974, 1459 DOI: 10.1039/P19740001459
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