Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 20, Pages 3934-3944Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000514
Keywords
Selenium; Selenium electrophiles; Alkenes; Cyclization; Heterocycles; Stereoselective synthesis
Categories
Funding
- Engineering and Physical Sciences Research Council (EPSRC) National Crystallography Service, Southampton
- School of Chemistry, Cardiff University
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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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