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

Abstract

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