title: Synthesis and rearrangement of a bridged thioamide.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, Lawrence, Kaas 66045-7852, USA.
authors.forename: Michal
authors.initials: M
authors.lastname: Szostak
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis; D007769:Lactams / Q000138:chemical synthesis; D015394:Molecular Structure; D013057:Spectrum Analysis; D013854:Thioamides / Q000138:chemical synthesis*
chemical_list: D001952:Bridged-Ring Compounds; D007769:Lactams; D013854:Thioamides