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Dienol-Benzene Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr192

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Dienol-Benzene Rearrangement. Comprehensive Organic Name Reactions and Reagents. 192:897–899.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The acid-promoted conversion of 4,4-disubstituted cyclohex-2,5-dienol into substituted benzene is generally known as the dienol-benzene rearrangement. This reaction is catalyzed only by H+ in acetate, formate, and phosphate buffers and the rearrangement for 4-methyl-4-trichloromethyl cyclohex-2,5-dienol has been found to be first-order kinetics. This reaction is helpful for introducing aromaticity into the A-ring of steroids.

Keywords:

  • 4-methyl-4-trichloromethyl cyclohex-2,5-dienol;
  • o-xylene;
  • carbonium ion;
  • steroids