Synthesis of Nonaphenylenes and Dodecaphenylenes Using Electron-transfer Oxidation of Lipshutz Cuprate Intermediates

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  • Masahiko Iyoda
    Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University
  • Mohammad Jalilur Rahman
    Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University
  • Aoi Matsumoto
    Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University
  • Mo Wu
    Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University
  • Yoshiyuki Kuwatani
    Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University
  • Kazumi Nakao
    Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University
  • Yoshihiro Miyake
    Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University

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Abstract

<jats:title>Abstract</jats:title> <jats:p>Nonaphenylene and its hexaalkyl derivatives have been synthesized using electron-transfer oxidation of Lipshutz cuprates with duroquinone. Oxidation of the Lipshutz cuprate derived from dibromo-o-terphenyl in THF produced nonaphenylene in moderate yield, whereas the similar oxidation of the Lipshutz cuprate derived from diiododiethyl-o-terphenyl in ether afforded the corresponding nonaphenylene and dodecaphenylene. Furthermore, oxidation of Lipshutz cuprate derived from diiododibutyl-o-terphenyl only gave the nonaphenylene.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 34 (11), 1474-1475, 2005-09-28

    Oxford University Press (OUP)

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