A Cycloaddition–Cyclodehydrogenation Route from Stilbenoids to Extended Aromatic Hydrocarbons

Authors

  • Dipl.-Chem. Markus Müller,

    1. Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350
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  • Dipl.-Chem. Heike Mauermann-Düll,

    1. Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350
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  • Dr. Manfred Wagner,

    1. Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350
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  • Dr. Volker Enkelmann,

    1. Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350
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  • Prof. Dr. Klaus Müllen

    Corresponding author
    1. Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350
    • Max-Planck-Institut für Polymerforschung Ackermannweg 10, D-55128 Mainz (Germany) Telefax: Int. code + (6131) 379350
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  • Dedicated to Professor Wolfram Grimme on the occasion of his 65th birthday

Abstract

original image

An unconventional route to planar graphitic fragments has been demonstrated with the novel synthesis of aromatic polycycles such as 2. The intramolecular Diels–Alder reaction of 1 is followed by aromatization and oxidative aryl–aryl coupling to afford 2 (C30H16) in high yield. The analogous synthesis of a C54H22 polyarene shows that this approach can be used to prepare larger graphitic sections.

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