Iodohexene Radical Cyclisation Endo

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

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

Even though the six membered ring gives a stabilised radical as an intermediate, the formation of the five membered exo product is more favoured. The reaction proceeds via an abstraction of iodine by a trimethyltin radical. The chain can then twist into a position to cyclise. Not shown here is the abstraction of hydrogen from trimethyltinhydride by the methylcyclopentane radical to form the endo product.

Back to Radical Cyclisation Summary

H. Fischer and L. Radom, Angew. Chemie Int. Ed., 2001, 40, 1340–1371.

 

 

How useful was this page?

Click on a star to rate it!

Average rating / 5. Vote count:

As you found this post 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