The Preparation and Novel Sigmatropic Rearrangement of Cyclophanes having a Spiro Skeleton

DOI: 10.1039/c39920000865

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Journal of the Chemical Society. Chemical communications p. 865 - 866 (1992)

Update date:2022-07-30

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Authors:

Yamato, Takehiko

Matsumoto, Jun-ichi

Tokuhisa, Kiwamu

Suehiro, Kazuaki

Tashiro, Masashi

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Article abstract of DOI:10.1039/c39920000865

Oxidation of dihydroxymetacyclophanes 1 with K3 afforded the intramolecular O-C coupling product 2, which has a spiro skeleton in good yield; variable temperature 1H NMR measurements indicated that compounds 2 are interconvertible by a thermal <3.3> sigmatropic rearrangement, and the activation free energies for the <3.3> sigmatropic rearrangement increased with increasing length of the methylene bridge in compounds 2.

Full text of DOI:10.1039/c39920000865

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