Diels-Alder: s-cis conformation

Methyl acrylate and butadiene

Background Colour:

Sn2

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

Acylic dienes always react in the s-cis conformation. Butadiene normally prefers to be in the s-trans conformation for steric reasons. However it must adopt the unfavorable s-cis conformation, by rotating through its middle single bond to achieve a flat planar structure, before it reacts with the dienophile.

 

 

894