Zincke-Suhl reaction

Zincke-Suhl reaction

The Zincke-Suhl reaction is a special case of a Friedel-Crafts alkylation and was first described by Theodor Zincke and Suhl. [M Newman. "A Study of the Zincke and Suhl Reaction", "J. Am. Chem. Soc." 19(6) (1954) p978] [M Newman. "The Aluminum Chloride-catalyzed Reaction of Benzotrichloride with p-Cresol", "J. Am. Chem. Soc." 19(6) (1954) p985] [cite journal
title = Ueber die Einwirkung von Tetrachlorkohlenstoff und Aluminiumchlorid auf p-Kresol und p-Kresolderivate
author = Zincke, Th.; Suhl. R.
journal = Chemische Berichte
volume = 39
issue = 4
pages = 4148–4153
year = 1906
url =
doi = 10.1002/cber.190603904115
]

The classic example of this reaction is the conversion of p-cresol to a cyclohexadienone (with the aid of aluminium chloride as a catalyst and tetrachloromethane as a solvent). Melvin Newman, a scientist from the U.S. intensively studied the reaction in the 1950's and reported several improved procedures as well as mechanistic studies.

The reaction product is a starting material in the dienol benzene rearrangement.

References


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