期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2010, 期 20, 页码 3934-3944出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000514
关键词
Selenium; Selenium electrophiles; Alkenes; Cyclization; Heterocycles; Stereoselective synthesis
资金
- Engineering and Physical Sciences Research Council (EPSRC) National Crystallography Service, Southampton
- School of Chemistry, Cardiff University
New chiral sulfoxide-containing diselenides were prepared and their corresponding selenium electrophiles were used for the stereoselective functionalization of alkenes. The influence of solvents and different nucleophiles on the outcome of the selenenylation reaction was studied. Besides the successful selenenylation reactions, one selenium electrophile showed an unexpected reactivity in forming a six-membered heterocyclic system upon reaction with alkenes. A mechanism for the formation of these 2,3-dihydro-1,4-benzoselenothiine 1-oxides is proposed.
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