Rearrangements – Favorskii rearrangement

NOTE: Important charges and non-bonding electrons are shown throughout the animation except during the transition phase

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

Favorskii rearrangement of cyclic 2-bromoketones leads to a ring contraction. Enolization occurs on the side of the ketone away from the bromine atom and the enolate cyclizes. The cyclopropanone intermediate is symmetrical so that the product is the same whichever C–C bond breaks after nucleophilic attack by the methoxide ion.

N. H. Werstiuk, Tetrahedron, 1983, 39, 205–268.

()

How useful was this page?

Click on a star to rate it!

Average rating / 5. Vote count:

No votes so far! Be the first to rate this page.

As you found this page useful...

Follow us on social media!

We are sorry that this page was not useful for you!

Let us improve this page!

Tell us how we can improve this page (in your own language if you prefer)? If you would like a response, please include your email address e.g. [email protected]

Provided by the