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Alkene Reactions: Epoxidation using mCPBA (Baeyer Villiger Reaction)

meta-Chloroperoxybenzoic acid (mCPBA) and other peroxyacids (RCO3H) react with alkenes to form epoxides:

Alkene Reactions: Epoxidation using mCPBA (Baeyer Villiger Reaction) image1.png

If this reaction adds stereochemistry to the molecule, the two epoxide bonds are added in syn addition and are always in the same plane. This reaction also maintains the cis/trans positioning of functional groups after the epoxide ring has been formed:

Same plane

Alkene Reactions: Epoxidation using mCPBA (Baeyer Villiger Reaction) image1.png

No stereocenters

Alkene Reactions: Epoxidation using mCPBA (Baeyer Villiger Reaction) image2.png

The reaction mechanism is depicted below:

Alkene Reactions: Epoxidation using mCPBA (Baeyer Villiger Reaction) image3.png

In the first step, many electron movements are shown but this depicts more of an intermediate product than a discrete step. The electrons from the alkene bond react with the OH group of mCPBA to form a ring structure. Simultaneously, electrons from the Oxygen-Oxygen bond shift over to mCPBA from the OH group, allowing the double bonded O on mCPBA to attack the H atom from the OH group, resulting in epoxide formation

The reagents used for this reaction are mCPBA or other peroxyacids (RCO3H).