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Formation of a new benzotriquinane skeleton via intramolecular photocycloaddition reactions of a phenylethynes moiety to a 1-cyanonaphthalene ring system

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Abstract

Photoirradiation of 1-cyano-2-(2,2-dicyano-5-phenylpentyn-4-yl)naphthalene and its analogues promotes sequential intramolecular [2π + 2π] photocycloaddition and cyclobutene ring opening to form benzocyclooctatetraenes, which are then transformed to benzotriquinanes in good yields via a photochemical transannular cyclization process.

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Author notes

  1. Kazuhiko Mizuno

    Present address: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5, Takayama-cho, Ikoma, Nara, 630-0192, Japan

  2. Hajime Maeda

    Present address: Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kanazawa, Ishikawa, 920-1192, Japan

Authors and Affiliations

  1. 1-1 Gakuen-cho, Sakai, Osaka, 599-8531, Japan

    Kazuhiko Mizuno, Naoki Negoro, Yoshinori Nagayama, Hajime Maeda & Hiroshi Ikeda

Authors
  1. Kazuhiko Mizuno
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  2. Naoki Negoro
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  3. Yoshinori Nagayama
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  4. Hajime Maeda
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  5. Hiroshi Ikeda
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Correspondence to Kazuhiko Mizuno.

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Dedicated to the memory of Professor Nicholas J. Turro (Columbia University).

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Mizuno, K., Negoro, N., Nagayama, Y. et al. Formation of a new benzotriquinane skeleton via intramolecular photocycloaddition reactions of a phenylethynes moiety to a 1-cyanonaphthalene ring system. Photochem Photobiol Sci 13, 145–148 (2014). https://doi.org/10.1039/c3pp50243k

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