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Catalysis Letters

, Volume 119, Issue 3–4, pp 296–303 | Cite as

Fused Polycyclic Hydrocarbons Through Superacid-Induced Cyclialkylation of Aromatics

  • István Ledneczki
  • Peter Forgo
  • Árpád Molnár
Article

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.

Keywords

Alkylation Cyclialkylation Arenes Carbocations Superacid 

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Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • István Ledneczki
    • 1
  • Peter Forgo
    • 1
  • Árpád Molnár
    • 1
  1. 1.Department of Organic ChemistryUniversity of SzegedSzegedHungary

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