Enantiomerically enriched thiiranium ion 5 has been prepared by silverassisted ionization of chloro sulfide 4 at -20°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 racemization processes.
- Episulfonium ions lewis bases
- Stereoselectivity sulfur
ASJC Scopus subject areas
- Organic Chemistry