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Zincke-Suhl Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr700

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Zincke-Suhl Reaction. Comprehensive Organic Name Reactions and Reagents. 700:3178–3182.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The preparation of 4-methyl-4-trichloromethyl cyclohexa-2,5-dienone by treatment of p-cresol with aluminum chloride in carbon tetrachloride is generally referred to as the Zincke–Suhl reaction. This reaction has been compared with the Friedel–Crafts alkylation. The study finds that BF3 and SnCl4 are not effectual activators for the Zincke–Suhl reaction. Furthermore, three locations as possible reaction sites have been noticed in the reaction of p-cresol with CCl4 in the presence of AlCl3. It has been reported that the 4-alkyl-4-trichloromethyl-cyclohexa-2,5-dienones practically undergo rearrangements to resume the aromaticity in the presence of an acid, affording various products, depending on the structure of substituted cyclohexa-2,5-dienones and the reaction conditions. The migratory aptitude of groups follow the Pinacol rearrangement, where a phenyl group is a preferred group compared to methyl group. This reaction has wide applications in organic synthesis.

Keywords:

  • aluminum trichloride;
  • carbon tetrachloride;
  • p-cresol;
  • resorcinol