Diels-Alder – Stereochemistry of the E,E-diene (trans-trans)

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

The two CH₃ groups appear beneath the new six-membered ring, with the hydrogens above. There is a plane of symmetry throughout and the products must have this symmetry too, because the reaction is concerted and no significant movement of substituents can occur.

Back to Diels-Alder summary

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