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Fused Polycyclic Hydrocarbons Through Superacid-Induced Cyclialkylation of Aromatics

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Abstract

Benzene and substituted derivatives (toluene, ortho-xylene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, anisole), when applied in large excess, react with 1,4 diols (pentan-1,4-diol, hexan-2,5-diol, and 2,5-dimethylhexan-2,5-diol) or an oxolane (2,2,5,5-tetramethyltetrahydrofuran) in the presence of the Brønsted superacid trifluoromethanesulfonic acid (triflic acid, TFSA) to afford substituted tetralins in excellent yields with high selectivity. Reacting benzene with a small excess of alkylating agents yields octahydroanthracenes. The transformation of naphthalene with oxolane leads to a partially saturated octamethyloctahydrotetracene under similar conditions. Product formation is interpreted by intermolecular Friedel-Crafts alkylation followed by cyclialkylative ring closure.

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Authors and Affiliations

  1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, 6720, Hungary

    István Ledneczki, Peter Forgo & Árpád Molnár

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  1. István Ledneczki
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  2. Peter Forgo
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  3. Árpád Molnár
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Correspondence to Árpád Molnár.

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Ledneczki, I., Forgo, P. & Molnár, Á. Fused Polycyclic Hydrocarbons Through Superacid-Induced Cyclialkylation of Aromatics. Catal Lett 119, 296–303 (2007). https://doi.org/10.1007/s10562-007-9234-2

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  • DOI: https://doi.org/10.1007/s10562-007-9234-2

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