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Tandem Ring Expansion of Alkenyl Benzocyclobutenol Derivatives into Substituted Naphthols

Authors

  • Toshiyuki Hamura Dr.,

    1. Department of Chemistry, Tokyo Institute of Technology, and SORST, Japan Science and Technology Agency (JST), 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • Takeaki Suzuki,

    1. Department of Chemistry, Tokyo Institute of Technology, and SORST, Japan Science and Technology Agency (JST), 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • Takashi Matsumoto Dr.,

    1. Department of Chemistry, Tokyo Institute of Technology, and SORST, Japan Science and Technology Agency (JST), 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • Keisuke Suzuki Prof. Dr.

    1. Department of Chemistry, Tokyo Institute of Technology, and SORST, Japan Science and Technology Agency (JST), 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • This research was partially supported by the 21st Century COE program and Grant-in-Aid for Young Scientists (B). T.S. is grateful to JSPS for a predoctoral fellowship.

Abstract

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Twice expanded: Substituted naphthols were prepared in a novel synthetic route starting from alkenyl benzocyclobutenol derivatives. The conversion includes two successive ring-enlargement processes (ABC; see scheme). The halonium ion (X+) induces expansion of the four-membered ring to a five-membered ring, and SmI2 promotes the expansion of the five-membered ring to the six-membered ring with concomitant elimination of ROSmI2.

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