Double bond geometry

Conjugate addition of peroxide to form epoxides (E-enone)

Background Colour:

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

Epoxidation of the E-enone is relatively quick to complete and the epoxide is isolated in a high yield. The mechanism involves conjugate addition and ring closure with cleavage of the weak O-O bond. The closure of the three-membered ring is fast enough to preserve the stereochemistry of the intermediate enolate.

Back to previous page