Cox, Charles T. Department of Chemistry, Duke University, Durham, North Carolina.
Last reviewed:February 2021
- Reaction mechanism
- Diene structure
- Dienophile structure
- Molecular orbital theory
- More about stereochemistry
- Substituents on the diene
- Related Primary Literature
- Additional Reading
A cycloaddition reaction between a diene and a dienophile. The simplest Diels-Alder reaction (O. Diels and K. Alder, 1928) occurs between butadiene and ethylene and is often referred to as a [4+2] cycloaddition. The numbers, four and two in brackets, are associated with the number of π electrons in the butadiene and ethylene molecules. In the Diels-Alder reaction, two π bonds are broken and two carbon-carbon σ bonds are formed. The terms diene and dienophile are generally used to define the specific reactants in the Diels-Alder reaction. In reaction (1), butadiene (1) is the diene, and ethylene (2) is the dienophile.
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