Catalytic Epoxidation of Alkenes with Oxone

Scott E. Denmark, David C. Forbes, David S. Hays, Jeffrey S. DePue, Richard G. Wilde

Research output: Contribution to journalArticle

Abstract

A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed. The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group. Optimal epoxidation conditions employ 10 mol % of l-dodecyl-l-methyl-4-oxopiperidinium triflate (8d+OTf-) in a CH2CI2/PH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant. Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5—8.0, (3) iV-dodecyl chain, and (4) the triflate salt as key experimental and structural variables. A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83—96% yield.

Original languageEnglish (US)
Pages (from-to)1391-1407
Number of pages17
JournalJournal of Organic Chemistry
Volume60
Issue number5
DOIs
StatePublished - Mar 1 1995

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Denmark, S. E., Forbes, D. C., Hays, D. S., DePue, J. S., & Wilde, R. G. (1995). Catalytic Epoxidation of Alkenes with Oxone. Journal of Organic Chemistry, 60(5), 1391-1407. https://doi.org/10.1021/jo00110a049