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Preparation of Novel Selenopenams by Intramolecular Homolytic Substitution
School of Chemistry, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, Australia
* Author to whom correspondence should be addressed.
Received: 17 February 2004 / Accepted: 20 February 2004 / Published: 31 May 2004
Abstract: 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.
Keywords: Free radical; homolytic substitution; selenium; β-lactam.
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MDPI and ACS Style
Carland, M.W.; Schiesser, C.H. Preparation of Novel Selenopenams by Intramolecular Homolytic Substitution. Molecules 2004, 9, 466-471.
Carland MW, Schiesser CH. Preparation of Novel Selenopenams by Intramolecular Homolytic Substitution. Molecules. 2004; 9(6):466-471.
Carland, Michael W.; Schiesser, Carl H. 2004. "Preparation of Novel Selenopenams by Intramolecular Homolytic Substitution." Molecules 9, no. 6: 466-471.