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.

REFERENCE

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

B. L. DIATKIN

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