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von Auwers Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr646

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. von Auwers Rearrangement. Comprehensive Organic Name Reactions and Reagents. 646:2892–2895.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The thermal or an acid promoted rearrangement of alkylidene-4-(dichloromethyl)-4-methyl cyclohexadienes to the corresponding benzene derivatives in which the dichloromethyl group migrating to the α-carbon atom of the alkylidene side chain, is generally referred to as the von Auwers rearrangement. The driving force for the von Auwers rearrangement can probably be attributed to the aromatization. It has been observed that this rearrangement generally involves either a 1:2 shift of the methyl group or a 1:3 or 1:5 shift of the trichloromethyl group. Moreover, this rearrangement usually requires an induction period, which can be reduced when benzoyl peroxide is added. This reaction has limited application in organic synthesis.

Keywords:

  • Reimer–Tiemann reaction;
  • p-substituted phenol;
  • Zincke–Suhl product;
  • trichloromethyl group