I believe this may be a Diels-Alder reaction, but the benzyl group on the edge does not serve a an electron donating group and more as a stabilizing group.

I am at a loss for what reaction would take place if the Diels-Alder reaction doesn't.


1 Answer 1


The presence of an electron-donating group on the diene, or an electron-withdrawing group on the dienophile, is not an absolute requirement for the Diels-Alder reaction to occur. There are many Diels-Alder reactions that don't have such features.

In any case, the cyano groups on the dienophile are electron-withdrawing groups. So, it's still a pretty favourable scenario for the Diels-Alder to occur.

Reaction mechanism

Since the dienophile is symmetrical there aren't any regioselectivity issues, and the relative stereochemistry of the two cyano groups in the product will be determined by the configuration of the double bond in the dienophile. A trans or (E) double bond will lead to the trans dinitrile (both enantiomers of it), and a cis or (Z) double bond will give rise to the cis dinitrile.

By the way, according to your title, there's no benzyl group on the diene, only a phenyl group. (Not that it makes much of a difference, though.)


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