Definition

Epoxides or oxacyclopropanes can be obtained by reaction so-called epoxidation from alkenes with peroxy acids.

Structural reaction scheme for Epoxide formation [from alkenes], diagram 1 of 3
Figure 1. Epoxide formation [from alkenes]

Explanation

The most commonly used peroxy acids are meta-chloroperoxybenzoic acid (MCPBA) and peroxyacetic acid.


This reaction is stereospecific. If we start with cis-alkene we will obtain cis-epoxide. The same applies to trans-isomers.

Structural reaction scheme for Epoxide formation [from alkenes], diagram 2 of 3
Figure 2. Epoxide formation [from alkenes]
Structural reaction scheme for Epoxide formation [from alkenes], diagram 3 of 3
Figure 3. Epoxide formation [from alkenes]