Radical Additions to (η6-Arene)(tricarbonyl)-chromium Complexes: Diastereoselective Synthesis of Hydrophenalene and Hydrobenzindene Derivatives by Samarium(II) Iodide Induced Cyclization

Authors

  • Prof. Dr. Hans-Günther Schmalz,

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    1. Institut für Organische Chemie der Technischen Universität, Strasse des 17. Juni 135, D-10623 Berlin (Germany), Telefax: Int. code + (30)314-21105
    • Institut für Organische Chemie der Technischen Universität, Strasse des 17. Juni 135, D-10623 Berlin (Germany), Telefax: Int. code + (30)314-21105
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  • Dipl.-Chem. Stephan Siegel,

    1. Institut für Organische Chemie der Technischen Universität, Strasse des 17. Juni 135, D-10623 Berlin (Germany), Telefax: Int. code + (30)314-21105
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  • Dr. Jan W. Bats

    1. Institut für Organische Chemie der Universität Frankfurt am Main (Germany)
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  • This work was supported by the Volkswagen-Stiftung, the Fonds der Chemischen Industrie, and Schering AG. We thank Prof. Dr. H. Schumann, Berlin, for a gift of samarium metal.

Abstract

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Yes indeed, radical additions to arene-Cr(CO)3 complexes are possible. Treatment of the chiral complex 1 with SmI2 gives tricycle 2 selectively by a 5-endo-trig radical cyclization; dihydro-1 is converted into the demethoxylated complex 3. In the latter case the ketyl radical adds directly to the complexed arene.

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