Oxidation of Alkenes with Aqueous Potassium Peroxymonosulfate and No Organic Solvent

Article abstract of DOI:10.1021/jo00025a014

Aqueous potassium peroxymonosulfate oxidizes water-immiscible alkenes at room temperature in the absence of organic solvent.Acidic (pH <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 > 6.7 with NaHCO3 enabled selective epoxidations of 2,3-dimethyl-2-butene, 1-methylcyclohexene, cyclohexene, styrene, and β-methylstyrene.The order of decreasing reactivity of alkenes was: 2,3-dimethyl-2-butene > 1-methylcyclohexene <*> cyclohexene > cyclooctene > α-methylstyrene <*> β-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.