The synthesis of a bridged thiolactam is described. This thiolactam is shown to undergo an unusual C–N bond cleavage reaction under conditions of its synthesis. Spectroscopic properties of the thiolactam indicate a considerable degree of twist of the thioamide bond.
M. Szostak and J. Aubé, Chem. Commun., 2009, 7122 DOI: 10.1039/B917508C
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