Prilezhaev epoxidation

What is Prilezhaev epoxidation?

The Prilezhaev epoxidation is a chemical process that involves the formation of epoxides through the reaction of alkenes with peracids. It is a transformation of alkenes with an isolated olefinic double bond into epoxides or glycols through oxidation with an organic peracid in a neutral organic medium. The Prilezhaev epoxidation was first reported in 1909 and is generally known as the Prilezhaev reaction.

Prilezhaev epoxidation - general reaction scheme - Prileschajew reaction
Prilezhaev epoxidation
Prilezhaev epoxidation - general reaction scheme - Prileschajew reaction
Prilezhaev epoxidation

The Prilezhaev epoxidation can be carried out in many common organic solvents using perbenzoic acid as the oxidant. This reaction is especially useful for the epoxidation of nonvolatile, water-insoluble olefins. The actual yields and reaction time depend on the peracid used and the number and nature of groups attaching to the olefinic double bond. The introduction of an electron-withdrawing group to a phenyl ring increases the electrophilicity and reactivity of perbenzoic acid, and the application of m-chloro-perbenzoic acid in epoxidation of olefins is specifically known as mCPBA epoxidation. The Prilezhaev epoxidation is tolerable for many functional groups, including aromatic ring, ester, and ether, and has shown excellent face selectivity for certain kinds of olefins.

References

Prileschajew, N. (1909), Oxydation ungesättigter Verbindungen mittels organischer Superoxyde. [Oxidation of unsaturated compounds by organic superoxides.] Ber. Dtsch. Chem. Ges., 42: 4811-4815. https://doi.org/10.1002/cber.190904204100

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