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Condensation of naphthalenediols with benzene in the presence of aluminum bromide: an efficient synthesis of 5-, 6-, and 7-hydroxy-4-phenyl-1- and 2-tetralones

✍ Scribed by Konstantin Yu. Koltunov

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 123 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.04.062

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✦ Synopsis

Isomeric 1,5-, 1,6-, 1,7-, 2,6-, and 2,7-naphthalenediols react smoothly with benzene at room temperature in the presence of an excess of aluminum bromide to give 5-, 6-, and 7-hydroxy-4-phenyl-1-tetralones and 5-and 6-hydroxy-4-phenyl-2-tetralones, respectively. The mechanism of these reactions is interpreted in terms of key di-or tri-cationic (superelectrophilic) intermediates.

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