von Auwers Rearrangement
Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. von Auwers Rearrangement. Comprehensive Organic Name Reactions and Reagents. 646:2892–2895.
- Published Online: 15 SEP 2010
Choose one or more boxes to highlight terms.
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.
- Reimer–Tiemann reaction;
- p-substituted phenol;
- Zincke–Suhl product;
- trichloromethyl group