A Strain-Releasing Trap for Highly Reactive Electrophiles: Structural Characterization of Bowl-Shaped Arenium Carbocations

Authors

  • Dr. Alexander V. Zabula,

    1. Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222 (USA), Fax: (+1) 518-442-3462
    Search for more papers by this author
  • Sarah N. Spisak,

    1. Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222 (USA), Fax: (+1) 518-442-3462
    Search for more papers by this author
  • Dr. Alexander S. Filatov,

    1. Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222 (USA), Fax: (+1) 518-442-3462
    Search for more papers by this author
  • Dr. Andrey Yu. Rogachev,

    1. Institute für Anorganische und Angewandte Chemie, Universität Hamburg, 20146 Hamburg (Germany)
    Search for more papers by this author
  • Prof. Dr. Marina A. Petrukhina

    Corresponding author
    1. Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222 (USA), Fax: (+1) 518-442-3462
    • Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222 (USA), Fax: (+1) 518-442-3462
    Search for more papers by this author

  • Financial support of this work from the National Science Foundation Career Award (CHE-0546945) is gratefully acknowledged. We also thank Prof. L. T. Scott (Boston College) for fruitful discussions.

Abstract

original image

Falle für Elektrophile: Bei der Reaktion von Corannulen mit Halogenkohlenwasserstoffen in Gegenwart von AlCl3 entstehen die Produkte des elektrophilen Angriffs an einem der zentralen Kohlenstoffatome des gekrümmten aromatischen Systems (siehe Bild). Die Röntgenstrukturanalyse einer Reihe schalenförmiger Kationen führt die Verzerrungen infolge dieser ortsspezifischen Funktionalisierung vor Augen.

Ancillary