Prilezhaev Reaction

In 1909, Russian chemist Nikolai Alexandrovich Prilezhaev demonstrated the oxidation of isolated double bonds to the corresponding oxiranes (epoxides) using peroxycarboxylic acids. The reaction subsequently became known as the Prilezhaev reaction. This method of using peroxycarboxylic acids to prepare oxiranes is among the most widely used, unless an enantiomerically pure form is required, for which other methods such as the Shi asymmetric epoxidation can be utilized.

The most commonly used reagent for this reaction is the commercially available meta-chloroperoxybenzoic acid (mCPBA). However, other possible reagents include magnesium monoperphthalate and peracetic acid.

Epoxidation is one of the most frequently used reactions in organic chemistry. It is a commercially important reaction as epoxidation followed by polymerizaton gives glycols or polyoxoalkylenes, which are used as detergents, lubricants, waxes, and components of hydraulic liquids.