Intramolecular Radical Cyclisation Reaction

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 reaction is initiated much in the same way as the “SnMe3” radical chain whereby azobis(isobutyronitrile) homolyses to form two 2-cyanoprop-2yl radicals and nitrogen gas. As the alkene is not activated in this case the radical prefers to attack the weak carbon to sulfur bond. The resultant alkyl radical is stabilised by interactions with the oxygen lone pair raising the SOMO’s energy. Cyclisation is now favoured as the alkene double bond is held close to the alkyl radical. Finally abstraction of a hydrogen from tin hydride leads to the product and the tin radical carries the chain.

B. Giese, Angew. Chemie Int. Ed. English, 1985, 24, 553–565.

()

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