Rearrangements – Beckmann rearrangement

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

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

The mechanism of the Beckmann rearrangement follows the same pattern as a pinacol reaction – acid converts the oxime OH into a leaving group, and an alkyl group migrates on to the nitrogen as water departs. The product cation is then trapped by water to give an amide. This rearrangement is not confined to cyclic oximes, and other ways of converting OH to a leaving group also work, such as PCl5, SOCl2, and other acyl or sulfonyl chlorides.

B. Jones, Chem. Rev., 1944, 35, 335–350.


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