An Effective Catalytic Epoxidation of Terpenes with Hydrogen Peroxide under Organic Solvent-Free Conditions

被引：17
|
作者：
Kon, Yoshihiro [1 ]
Ono, Yutaka [1 ]
Matsumoto, Tomohiro [1 ]
Sato, Kazuhiko [1 ]
机构：
[1] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
来源：
SYNLETT | 2009年 / 07期
关键词：
oxidations; catalysis; epoxides; terpenoids; green chemistry; HALIDE-FREE CONDITIONS; SELECTIVE EPOXIDATION; FREE OXIDATION; TERMINAL OLEFINS; PRACTICAL METHOD; ADIPIC ACID; MONOTERPENES; ALCOHOLS; SYSTEM; ALKENES;
D O I：
10.1055/s-0028-1088156
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic system that operates well for the epoxidation of alpha-pinene, a very challenging Substrate, at near-neutral pH and ambient temperature without organic solvent was developed. With hydrogen peroxide as a terminal oxidant, combination of Na2WO4, PhP(O)(OH)(2), and [Me(n-C8H17)(3)N]HSO4 successfully catalyzed the epoxidation of alpha-pinene to give a-pinene oxide in 95% selectivity at 91% conversion, while the previously published conditions that use NH2CH2P(O)(OH)(2) as a promoter provide no epoxide. The method is also well applicable to the epoxidation of the other acid-sensitive terpenes.
引用
收藏
页码：1095 / 1098
页数：4
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