Diels-Alder – 2,3-Dimethylbutadiene and Acrolein(propenal)

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

Diels-Alder reactions occur between a conjugated diene and a dienophile (an alkene). This reaction shows a simple diene combining with an unsaturated aldehyde, which acts as the dienophile.

Notice how the diene has to rotate into an unfavorable s-cis coplanar conformation for the reaction to proceed and the carbonyl group occupies the endo position in the transition state.

J. Sauer, Angew. Chemie Int. Ed. English, 1966, 5, 211–230.

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