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Retro-Ene Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr534

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Retro-Ene Reaction. Comprehensive Organic Name Reactions and Reagents. 534:2373–2377.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The intramolecular thermolysis of organic compounds with an unsaturated functional group involving the transfer of a γ-hydrogen to the unsaturated center via a six-membered transition state to yield both ene and enophil is generally known as the retro-ene reaction or retro-ene fragmentation. The study finds that in most cases, this reaction involves a concerted mechanism, and gives a product with the stereochemical integrity preserved. This reaction does not take place among cyclic alkenes smaller than a seven-membered ring or fused rings except for a cyclopropyl ring. This reaction has broad applications in organic synthesis.

Keywords:

  • γ-hydrogen;
  • cyclopropyl ring;
  • pericyclic reactions;
  • cyclic alkenes