Issue 12, 1992

The preparation and novel [3.3] sigmatropic rearrangement of cyclophanes having a spiro skeleton

Abstract

Oxidation of dihydroxy[n.2]metacyclophanes 1 with K3[Fe(CN)6] 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.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1992, 865-866

The preparation and novel [3.3] sigmatropic rearrangement of cyclophanes having a spiro skeleton

T. Yamato, J. Matsumoto, K. Tokuhisa, K. Suehiro and M. Tashiro, J. Chem. Soc., Chem. Commun., 1992, 865 DOI: 10.1039/C39920000865

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