OXIDATION OF ALKENES WITH AQUEOUS POTASSIUM PEROXYMONOSULFATE AND NO ORGANIC-SOLVENT

被引：89

作者：

ZHU, WM ^{[1
]}

FORD, WT ^{[1
]}

机构：

[1] OKLAHOMA STATE UNIV,DEPT CHEM,STILLWATER,OK 74078

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 25期

关键词：

D O I：

10.1021/jo00025a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aqueous potassium peroxymonosulfate oxidizes water-immiscible alkenes at room temperature in the absence of organic solvent. Acidic (pH less-than-or-equal-to 1.7) solutions of 2KHSO5.KHSO4.K2SO4 in Water produced the epoxide from cyclooctene and diols from all other reactive alkenes investigated. Adjustment of initial pH to greater-than-or-equal-to 6.7 with NaHCO3 enabled selective epoxidations of 2,3-dimethyl-2-butene, 1-methylcyclohexene, cyclohexene, styrene, and beta-methylstyrene. The order of decreasing reactivity of alkenes was: 2,3-dimethyl-2-butene > 1-methylcyclohexene greater-than-or-equal-to cyclohexene > cyclooctene > alpha-methylstyrene greater-than-or-equal-to beta-methylstyrene > styrene > p-methylstyrene > allylbenzene. 1-Octene and tetrachloroethylene did not react. Phase-transfer catalysts, a colloidal cationic polymer, and a cationic surfactant microemulsion had little effect on the reaction.

引用

页码：7022 / 7026

页数：5

共 28 条

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BALL DI, 1959, J AM CHEM SOC, V78, P1125

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