Anionically induced decomposition of ethyl 2-(2,2-dimethylethylperoxymethyl)propenoate by amines: an easy access to amino epoxyesters and amino esterperoxides

Treatment of ethyl 2-(2,2-dimethylethylperoxymethyl)propenoate with primary and secondary amines led to amino epoxides and/or amino peroxides. These c ompounds were produced by the addition of the amine to the unsaturation of the peroxide to form a zwitterion, followed, respectively, by a proton tran sfer and an S(N)i reaction. The formation of one or the other amino derivat ive was favoured by different reaction conditions (mode of addition of the reactant, solvent). Easy separation of these compounds was possible by chro matography on silica when the reaction was unselective.