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Electrochemical Enol Ether/Olefin Cross-Metathesis in a Lithium Perchlorate/Nitromethane Electrolyte Solution†

Authors

  • Teppei Miura,

    1. Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan, Fax: (+81) 42-360-7167
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  • Shokaku Kim Dr.,

    1. Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan, Fax: (+81) 42-360-7167
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  • Yoshikazu Kitano Prof.,

    1. Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan, Fax: (+81) 42-360-7167
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  • Masahiro Tada Prof.,

    1. Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan, Fax: (+81) 42-360-7167
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  • Kazuhiro Chiba Prof.

    1. Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan, Fax: (+81) 42-360-7167
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  • †

    This work was partially supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology and the Japan Society for the Promotion of Science.

Abstract

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Electrolytically generated four-membered-ring radical-cation intermediates are involved in the anodic olefin cross-metathesis of enol ethers and olefins in a lithium perchlorate/nitromethane electrolyte solution (see scheme). The reaction mechanism was investigated through deuterium-labeling studies.

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Article Information

DOI

10.1002/anie.200503656

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Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • alkenes;
  • electrochemistry;
  • enol ethers;
  • metathesis;
  • oxidation

Publication History

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  • Manuscript Received:

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