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A Möbius Antiaromatic Complex as a Kinetically Controlled Product in Phosphorus Insertion to a [32]Heptaphyrin

Authors

  • Tomohiro Higashino,

    1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 (Japan)
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  • Byung Sun Lee,

    1. Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
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  • Jong Min Lim,

    1. Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
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  • Prof. Dr. Dongho Kim,

    Corresponding author
    1. Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
    • Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
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  • Prof. Dr. Atsuhiro Osuka

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 (Japan)
    • Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 (Japan)
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  • This work was supported by Grants-in-Aid (No. 22245006 (A) and 20108001 “pi-Space”) for Scientific Research from MEXT. T.H. acknowledges a JSPS Fellowship for Young Scientists. The work at Seoul was supported by the Midcareer Researcher Program (2010-0029668) and World Class University (R32-2010-000-10217-0) Programs of MEST of Korea.

Abstract

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Singly twisted Möbius antiaromatic [34]heptaphyrin A and doubly twisted Hückel aromatic [34]heptaphyrin B were formed by a phosphorus insertion reaction. A rearranges thermally to give the more stable B with P[DOUBLE BOND]O migration from NNN to NNC, and thus A is a rare case of a kinetically controlled Möbius antiaromatic molecule.

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