The Journal of Organic Chemistry

Epoxidation of alkylidenecyanoacetic esters with hydrogen peroxide and related reactions

M Igarashi, H Midorikawa

Index: Igarashi,M.; Midorikawa,H. Journal of Organic Chemistry, 1967 , vol. 32, p. 3399 - 3407

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Citation Number: 5

Abstract

The reaction mechanism of alkylidenecyanoacetic esters with hydrogen peroxide in the presence of sodium tungstate or trisodium phosphate is discussed. It is concluded that the first step is the nucleophilic attack of the pertungstate anion (or perhydroxyl anion in the case of phosphate catalysis) on the double bond to give the corresponding epoxy nitrile, hydrolysis of which with alkaline hydrogen peroxide gives the epoxy amide. The fact that ...