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Retro-Diels-Alder Reaction

(Retro-Diels-Alder Cleavage, Retro-Diels-Alder Fragmentation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr533

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Retro-Diels-Alder Reaction. Comprehensive Organic Name Reactions and Reagents. 533:2367–2372.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The thermally allowed [π4+π2s] cycloreversion of an organic compound with a double bond in a six-membered ring, leading to the formation of a diene and a dienophile, i.e., the reversed process of the Diels–Alder cycloaddition. Thus this reaction is generally known as the retro-Diels–Alder fragmentation, or retro-Diels–Alder reaction.

Even though the Diels-Alder cycloaddition is thermodynamically reversible, the Diels-Alder cycloaddition products are fairly stable, and the retro-Diels-Alder reaction does not occur regularly. Besides the normal thermolysis of Diels-Alder cycloadducts, a few conditions have also been reported to facilitate the retro-Diels-Alder reaction. In addition, some special structural components may facilitate the retro-Diels-Alder reaction too. It has been mentioned that the thermal retro-Diels-Alder reaction of anthracene cycloadducts is accelerated by electron-donating groups. This reaction has very wide application in organic synthesis, such as the formation of quinones, benzoquinones, heterocycle, etc.

Keywords:

  • dienophile;
  • catalytic antibody;
  • Lewis acid;
  • bicyclo[2.2.2]octene