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