Carland Michael W, Schiesser Carl H
School of Chemistry, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, Australia.
Molecules. 2004 May 31;9(6):466-71. doi: 10.3390/90600466.
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.
4-(苄基硒基)-2-氮杂环丁烷7和20的硫代肟酸酯衍生物13和21的光解反应,以良好至中等的产率得到1-氮杂-7-氧代-4-硒杂双环[3.2.0]庚烷环系14和21,该过程可能涉及硒原子上的分子内均裂取代并伴有苄基自由基的消除。还描述了将该方法扩展用于制备1,2,2a-二氢-1H,8H-氮杂环丁烷并[2,1-b][1,3]苯并硒嗪-1-酮(22)的衍生物24。