期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 43, 页码 11737-11745出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901377
关键词
episulfonium ions; Lewis bases; nucleophiles; stereoselectivity; sulfur
资金
- National Science Foundation [CHE-0717989]
- Humboldt-Foundation
Enantiometrically enriched thiiranium ion 5 has been prepared by silver-assisted ionization of chloro sulfide 4 at -20 degrees C. This thiiranium ion is configurationally stable in solution up to room temperature as demonstrated by the stereospecific capture of the ion by various oxygen- and nitrogen-based nucleophiles. Both isolated olefins and weak Lewis bases can promote the racemization of 5 but these processes can also be suppressed at low temperature. Capture of 5 by methanol is faster than the racernization processes.
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