Abstract
The Michael addition of hydroperoxides on electron deficient olefines (phenyl vinylsulfonate; divinylsulfone, acrylic nitrile, methyl acrylate) resulted in optimal yields of peroxides at room temperature in a heterogeneous system (tetrachloroethylene/water) using lithium hydroxide and a hydroperoxide: base ratio of 1:1. The reaction with vinyl methyl ketone was carried out at-10 to-5° in excess of hydroperoxide as solvent. Vinyl phenylketone yielded the epoxide. With hydrogen peroxide only vinylsulfonic ester and divinylsulfone yielded the Michael adduct; otherwise the epoxides were obtained. The influence of the substituents on the olefines on the direction of reaction is discussed on the basis of the protonation rate of the intermediate carbanions.
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