Preparation of novel selenopenams by intramolecular homolytic substitution.
Photolyses of the thiohydroximate ester derivatives 13 and 21 of the 4- (benzyl-seleno)-2-azetidinoines 7 and 20, afford the 1-aza-7-oxo-4-selenabicyclo- [3.2.0]heptane ring systems 14 and 21 in good to moderate yield in processes that presumably involve intramolecular homolytic substitution at selenium with expulsion of benzyl radical. Extension of this methodology to the preparation of derivatives 24 of 12,2a-dihydro-1H,8H-azeto[2,1-b][1,3]benzoselenazin-1-one (22) is also described.
Carland
Michael W
MW
School of Chemistry, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, Australia.
Schiesser
Carl H
CH
D001593:Benzyl Compounds / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D012643:Selenium / Q000737:chemistry; D047090:beta-Lactams / Q000737:chemistry
D001593:Benzyl Compounds; D005609:Free Radicals; D016566:Organoselenium Compounds; D047090:beta-Lactams; D012643:Selenium