Synthesis of Tetra- and Pentasubstituted Benzenes from Dimedone and Derivatives
- 1 January 1992
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1992 (12) , 1287-1291
- https://doi.org/10.1055/s-1992-26360
Abstract
Treatment of dimedone (5,5-dimethylcyclohexane-1,3-dione) and derivatives with one molar equivalent of sulfuric acid in trifluoroacetic anhydride leads, via sulfonation and a 1,2-methyl group migration, to a variety of dimethylresorcinol derivatives. The reaction has been performed on substrates bearing ester, alkoxy, halo and amino substituents to produce a variety of polysubstituted benzenes. Transient sulfonated intermediates were observed by NMR.Keywords
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