CATALYTIC EPOXIDATION OF ALKENES WITH OXONE

被引：217

作者：

DENMARK, SE

FORBES, DC

HAYS, DS

DEPUE, JS

WILDE, RG

机构：

[1] Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 05期

关键词：

D O I：

10.1021/jo00110a049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/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) N-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.

引用

页码：1391 / 1407

页数：17

共 104 条

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