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Improved efficiency and product selectivity in the photo-Claisen-type rearrangement of an aryl naphthylmethyl ether using a microreactor/flow system

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Abstract

Ultraviolet (UV) irradiation of 2-[(2,4,6-trimethylphenoxy)methyl]-1-(methoxycarbonyl)naphthalene promotes a photochemical reaction that gives a cyclohexa-2,4-dienone product arising from a photo-Claisen-type ortho-rearrangement and a phenol derivative arising from a meta-rearrangement, along with 1-methoxycarbonyl-2-methylnaphthalene and 1,2-bis[1-(methoxycarbonyl)naphthalen-2-yl]ethane. When this process is carried out in a microreactor/flow system, its efficiency is dramatically enhanced and selectivity of products is improved. The effects on efficiency and product selectivity caused by the microreactor/flow system are attributed to more efficient light absorption and the suppression of secondary reactions.

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Acknowledgments

This work was supported in part by Grant-in-Aids for Scientific Research on Priority Areas (417) (no. 17029058) and (432) (no. 17034056), Exploratory Research (no. 16655018), and Young Scientists (B) (no. 16750039) from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japan.

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Authors and Affiliations

  1. Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, 920-1192, Japan

    Hajime Maeda

  2. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Satoshi Nashihara, Hirofumi Mukae & Kazuhiko Mizuno

  3. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, 3-9-1 Bunkyo, Fukui, Fukui, 910-8507, Japan

    Yasuharu Yoshimi

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  1. Hajime Maeda
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  2. Satoshi Nashihara
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  3. Hirofumi Mukae
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  5. Kazuhiko Mizuno
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Correspondence to Hajime Maeda or Kazuhiko Mizuno.

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Maeda, H., Nashihara, S., Mukae, H. et al. Improved efficiency and product selectivity in the photo-Claisen-type rearrangement of an aryl naphthylmethyl ether using a microreactor/flow system. Res Chem Intermed 39, 301–310 (2013). https://doi.org/10.1007/s11164-012-0650-6

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