Abstract
ArS(ArSSAr)+ (arylbis(arylthio)sulfonium ions), which were generated and accumulated by the electrochemical oxidation of diaryl disulfides (ArSSAr) in CH2Cl2 at -78 °C, reacted with alkenes to give the corresponding diarylthio-substituted compounds in a stereospecific manner in good yields, when the reaction was quenched with a soft nucleophile, such as allylsilanes, ketene silyl acetals, and triethylamine. A mechanism involving the initial formation of an episulfonium ion followed by ring-opening by the attack of ArSSAr has been suggested. The reactions of ArS(ArSSAr)+ with alkynes also took place to give 1,2-diorganothio-substitued alkenes stereoselectively under similar conditions.
Original language | English |
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Pages (from-to) | 2823-2829 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 66 |
Issue number | 15 |
DOIs | |
Publication status | Published - Apr 10 2010 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry