Prilezhaev's Reaction

Prilezhaev’s Reaction


a method of obtaining α-oxides (oxides of olefins, oxiranes) by the interaction of olefins and organic peracids:

The oxidation of olefins with reduced electron density of the double bond (for example, α,β-unsaturated carbonyl compounds or fluorolefins) is effected by means of hydrogen peroxide in an alkaline solution (a modification of Prilezhaev’s reaction):

Prilezhaev’s reaction is used in organic synthesis and analysis for the quantitative determination of double bonds. In industry, the reaction facilitates the derivation of α-oxides from higher unsaturated fatty acids; these oxides are used as plasticizers for polymers. Prilezhaev’s reaction also makes possible the derivation of hexafluoropropylene oxide, used as a base for chemically stable lubricating oils and fluids. The reaction was discovered in 1909 by N. A. Prilezhaev.


Organicheskie reaktsii, collection 7. Moscow, 1956. Page 476. (Translated from English.)


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