Treatment of 2-ethoxycarbonylprop-2-enyl peroxides with potassium alkylperoxylate, the sodium enolate of diethyl malonate and a primary or secondary amine yields epoxides via a two-step process: (i) addition of the nucleophile to the acrylic unsaturated bond and (ii) intramolecular anionic substitution on the peroxidic bond.
Abstract Addition of potassium hydroxide to a THF solution of an alkyl hydroperoxide and an allylic peroxide having an electron-poor double bond yielded the formation of epoxyperoxide. Such a heterocycle was generated via the. Michael addition of the peroxylate to the activated double bond of the unsaturated peroxide followed by an SNI at the O-O bond.