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.
C. Cramay, R. Ferdinando, M. Degueil-Castaing and B. Maillard, Chem. Commun., 1998, 1855 DOI: 10.1039/A803300E
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