Communication

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

  1. Tomohiro Higashino1,
  2. Byung Sun Lee2,
  3. Jong Min Lim2,
  4. Prof. Dr. Dongho Kim2,*,
  5. Prof. Dr. Atsuhiro Osuka1,*

Article first published online: 19 NOV 2012

DOI: 10.1002/anie.201208147

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 52, pages 13105–13108, December 21, 2012

Additional Information

How to Cite

Higashino, T., Lee, B. S., Lim, J. M., Kim, D. and Osuka, A. (2012), A Möbius Antiaromatic Complex as a Kinetically Controlled Product in Phosphorus Insertion to a [32]Heptaphyrin . Angew. Chem. Int. Ed., 51: 13105–13108. doi: 10.1002/anie.201208147

Author Information

  1. 1

    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 (Japan)

  2. 2

    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)

  1. †

    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.

Publication History

  1. Issue published online: 18 DEC 2012
  2. Article first published online: 19 NOV 2012
  3. Manuscript Received: 10 OCT 2012

Funded by

  • MEXT. Grant Numbers: 22245006 (A), 20108001
  • JSPS. Grant Numbers: 2010-0029668, R32-2010-000-10217-0
  • MEST of Korea

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Keywords:

  • aromaticity;
  • heptaphyrins;
  • Möbius antiaromaticity;
  • phosphorus;
  • porphyrinoids
Thumbnail image of graphical abstract

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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