Claisen rearrangement – Sigmatropic rearrangement

E1

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

The Claisen rearrangement is a [3,3]-sigmatropic rearrangement. Count the number of atoms from the old to the new sigma bond and you will see there are 3 atoms in both directions round the ring. [3,3] sigmatropic rearrangements happen though a chair-like transition state. If there is a substituent on the saturated carbon next to the oxygen, then trans (E) geometry is strongly favoured in the product. This a consequence of the chair transition state favouring equatorial substituents and the concerted nature of pericyclic reactions.

Richard Windsor – Undergraduate Final Year Project 2008

J. Rehbein and M. Hiersemann, Synthesis (Stuttg)., 2013, 45, 1121–1159.

5
(1)

How useful was this page?

Click on a star to rate it!

Average rating 5 / 5. Vote count: 1

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)?

Provided by the