Synthesis and reactivity of enantiomerically enriched thiiranium ions

Scott E. Denmark, Thomas Vogler

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)11737-11745
Number of pages9
JournalChemistry - A European Journal
Volume15
Issue number43
DOIs
StatePublished - Nov 2 2009

Keywords

  • Episulfonium ions lewis bases
  • Nucleophiles
  • Stereoselectivity sulfur

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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