Regioselective epoxidation of allylic alcohols with monoperoxyphthalic acid in water

Allylic alcohols such as geraniol and nerol undergo epoxidation with peroxy acids in aqueous medium and produce the corresponding epoxides in high yield. The introduction of the surfactant cetyltrimethylammonium hydroxide increases the afforded yields in reactions involving magnesium monoperoxyphthalate and monoperoxyphthalic acid. The efficiency of the surfactant relies on the interaction of epoxidation reactivity, alcohol solubility and reactant orientation. Additionally, the regulation of the medium's pH determines the regioselectivity of the reaction.