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The Diels-Alder Reaction Quinones and Other Cyclenones

  1. Lewis W. Butz1,
  2. Anton W. Rytina2

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or005.03

Organic Reactions

Organic Reactions

How to Cite

Butz, L. W. and Rytina, A. W. 2011. The Diels-Alder Reaction Quinones and Other Cyclenones . Organic Reactions. 5:3:136–192.

Author Information

  1. 1

    United States Department of Agriculture, Bureau of Animal Industry

  2. 2

    Rohm and Haas Company, Inc., Resinous Products Division

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

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Abstract

Quinones and other cyclenones react by 1,4-addition with conjugated dienes. A typical example is the reaction of butadiene with p-benzoquinone yielding the diketohexahydronaphthalene. The direct synthesis of quinones with other cyclenones may be extended to provide a route to the preparation of fused-ring aromatic systems. It is also possible to prepare fused-ring ketones containing angular substituents. Diene syntheses described in this chapter may lead to the synthesis of compounds of steroidal structure. The stereochemcial configurations of Diels-Alder addition products have been discussed elsewhere in this series, This problem is exceedingly complex with products described in this chapter and is impossible to predict stereochemical configurations of the adducts with any certainty.

Keywords:

  • Diels-Alder reaction;
  • quinones;
  • cyclenones;
  • benzoquinone;
  • naphthaoquinones;
  • fused-ring ketones;
  • diene additions;
  • experimental conditions