Rearrangements – Semipinacol rearrangements of diazonium salts

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

When diazomethane adds to a ketone, the product undergoes a ring expansion by rearrangement of the intermediate. Cyclohexanone is more reactive as an electrophile than either cyclopentanone or cycloheptanone, so it ring expands cleanly to cycloheptanone.

Z.-L. Song, C.-A. Fan and Y.-Q. Tu, Chem. Rev., 2011, 111, 7523–7556.

 

 

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!

Provided by the