化学
过氧化氢
催化作用
烯丙基重排
产量(工程)
卤化物
烯烃纤维
钨酸盐
钨酸钠
有机化学
反应性(心理学)
基质(水族馆)
甲苯
医学
材料科学
替代医学
海洋学
病理
钨
冶金
地质学
作者
Kazuhiko Satō,Masayoshi Aoki,Masami Ogawa,Tadashi Hashimoto,David Panyella,Ryoji Noyori
摘要
A catalytic system consisting of sodium tungstate dihydrate, (aminomethyl)phosphonic acid, and methyltrioctylammonium hydrogensulfate, effects the epoxidation of olefins using 30% hydrogen peroxide with a substrate-to-catalyst molar ratio of 50—500. The reaction proceeds in high yield without solvents, or, alternatively, with added toluene under entirely halide-free conditions. Lipophilic ammonium hydrogensulfate, which replaces the conventional chloride, and an (α-aminoalkyl)phosphonic acid are crucial for the high reactivity. This method is operationally simple, environmentally benign, and much more economical than the oxidation with m-chloroperbenzoic acid, allowing for a large-scale preparation of epoxides. Various substrates including terminal olefins, 1,1- and 1,2-disubstituted olefins, cyclic olefins, and tri- and tetrasubstituted olefins as well as allylic alcohols, esters, α,β-unsaturated ketones, and ethers can be epoxidized in high yield. The scope and limitations of this new reaction system are discussed.
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