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Tandem Friedel−Crafts Annulation to Novel Perylene Analogues

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posted on 15.08.2008, 00:00 by Mark A. Penick, Mathew P. D. Mahindaratne, Robert D. Gutierrez, Terrill D. Smith, Edward R. T. Tiekink, George R. Negrete
Novel dialkyloxy- and dihydroxyoctahydroperylenes are regioselectively available via a new tandem Friedel−Crafts alkylation of tetrahydronaphthalene precursors followed by oxidative aromatization. Heating of 5-alkyloxy-1-tetralol with p-toluenesulfonic acid in sulfolane gave the corresponding octahydroperylenes in moderate yields. Studies with Lewis acids and tetralin-1,5-diol in acetonitrile at room temperature provided the 4,10-dihydroxy analogue cleanly, albeit in reduced yields. Examples of these new series of perylene analogues were partially oxidized to the corresponding contiguously aromatic, anthracene core products or fully aromatized to 3,9-dialkyloxyperylenes in good yields.