Diels-Alder: Z,Z (cis,cis) diene – Stereochemistry of the diene


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

The stereochemistry of the diene must be taken into account to predict the stereochemistry of the product. Cyclopentadiene diene is cis,cis (Z,Z), and so has two sets of substituents – inside and outside. The inside one is the bridging CH2 group, which has to end up on one side of the molecule (in this case, sticking up in the products), while the two green hydrogens are outside and remain so. In the product, they end up below the six-membered ring. The acetylene dienophile is chosen to simplify the structure of the product.

Examples of sterochemistry in trans,trans (E,E) and cis,trans (E,Z) dienes.

J. Sauer, Angew. Chemie Int. Ed. English, 1967, 6, 16–33.


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