Products of Diels-Alder Reactions

Cyclopentadiene is the diene (end Cs of the diene component are blue) and ethyne is the dienophile (Cs of the dienophile component are green).

The dienophile (Cs of the dienophile double bond are green) adds to the central ring (blue Cs) of anthracene. Note that the carboxylic acid groups (Os are red), which are trans in the dienophile, are trans in the product also. This is a result of syn addition on the dieneophile component.

Syn addition on the diene causes the ester groups to be cis. The end Cs of the diene component are blue, the Cs of the dienophile double bond are green, Os are red, and Ns are gold.

The end Cs of the diene component are blue, the Cs of the dienophile double bond are green, and the Os are red.

This is an intramolecular Diels-Alder reaction. The end Cs of the diene component are blue, the Cs of the dienophile double bond are green, and the O is red.

The product has endo geometry. The end Cs of the diene component are blue, the Cs of the dienophile double bond are green, and the Os are red.

The "para-like" product is preferred. The end Cs of the diene component are blue, the Cs of the dienophile double bond are green, and the Os are red.

Because addition is syn on the dienophile, the carboxylic acid groups, which are trans in the dienophile reactant, are trans in the product. The end Cs of the diene component are blue, the Cs of the dienophile double bond are green, and the Os are red.

The end Cs of the diene component are blue, the Cs of the dienophile double bond are green, the N is gold, and the Os are red.

Both of the double bonds of the six-membered ring diketone react as dienophiles. The end Cs of the diene components are blue, the Cs of the dienophile double bonds are green, and the Os are red.