Standard Article

Diels-Alder Reaction

(Diels-Alder Condensation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr190

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Diels-Alder Reaction. Comprehensive Organic Name Reactions and Reagents. 190:886–891.

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

This reaction is an electrocyclic [4+2]-cycloaddition between a conjugated diene and a dienophile (either alkene or alkyne) for the synthesis of an unsaturated six-membered ring and it is generally known as the Diels–Alder reaction. The products from this reaction are called cycloadducts. In this reaction, the substituents on diene and dienophile both play very important roles, as they all affect the electron densities and orbital energy of the reactants. This reaction is also reported to show high regioselectivity, diastereoselectivity, and enantioselectivity, which are controlled by the compatibility between the HOMO–LUMO pairs of dienes and dienophiles. The study finds that the introduction of an atom other than carbon to either dienes or dienophiles results in the hetero-Diels–Alder reaction. Many modifications have been done on these reactions, such as application of high pressure, Lewis acid, and ultrasound radiation.

Keywords:

  • cycloadducts;
  • diene;
  • LUMO energy;
  • HOMO energy