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

The diene has two sets of substituents, inside and outside. The inside one is the bridging CH₂ group and it has to end up on one side of the molecule, whilst the two hydrogens are outside and remain so.

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

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