Oxidative Cyclodimerization After Tandem Cyclization of Dehydrobenzo[14]annulenes Induced by Alkyllithium

Authors

  • Shunpei Nobusue,

    1. Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531 (Japan)
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  • Dr. Akihiro Shimizu,

    1. Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531 (Japan)
    2. Present address: Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto (Japan)
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  • Prof. Kenji Hori,

    1. Division of Material Sciences, Graduate School of Science and Engineering, Yamaguchi University, Yamaguchi (Japan)
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  • Dr. Ichiro Hisaki,

    1. Department of Material and Life Science, Graduate School of Engineering, Osaka University, Osaka (Japan)
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  • Prof. Mikiji Miyata,

    1. Department of Material and Life Science, Graduate School of Engineering, Osaka University, Osaka (Japan)
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  • Prof. Yoshito Tobe

    Corresponding author
    1. Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531 (Japan)
    • Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531 (Japan)
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  • This work was supported by a The Grants-in-Aid for Scientific Research on Innovative Areas “Organic Synthesis based on Reaction Integration” (No. 2105). The synchrotron radiation experiments were performed at the BL38B1 of SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (proposal No. 2009B1969 and 2010A1427). We are grateful to Dr. K. Miura, Dr. S. Baba, and Dr. N. Mizuno for crystallographic data collection, and Prof. Kendall N. Houk of the University of California, Los Angeles for his advice on the theoretical studies.

Abstract

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Kondensiert: Bei Umsetzungen von Dehydrobenzo[14]annulenen mit n-Butyllithium wurde eine neuartige oxidative Cyclodimerisierung entdeckt, die in bis zu 30 % Ausbeute zu achtgliedrigen Ringen führt. Die Produkte enthalten zwei Indeno[2,1-a]fluoren-Einheiten, die durch eine Einfach- und eine Doppelbindung verknüpft sind, die aus drei transannularen Bindungsbildungen resultieren.

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