Epoxidation of alkene
Abstract
One way to synthesize an epoxide is to react an alkene with a peroxycarboxylic acid (commonly, the meta-chloroperbenzoïc acid (m-CPBA) is used). This reaction proceeds with retention of the initial alkene configuration.
Keywords
Alkene, Peroxy acid, m-CPBA, Epoxide
Category
Alkene
Mechanism
This reaction proceeds via a concerted mechanism in a single step. The alkene 𝜋 bond acts as a nucleophile and attacks the electrophilic oxygen atom of the peroxy acid, the one bearing the hydrogen. Simultaneously, the lone electron pair from this same oxygen attacks the electrophilic side of the alkene. The O-O bond breaks and the hydroxyl proton is transferred intramolecularly to the carbonyl oxygen of the peroxy acid, generating a carboxylic acid as a by-product.
