The 2-‘phenol’ in the tricyclic [10]annulene series appears to exist entirely in the keto form (4); the ‘phenolate’ anion is readily formed, and can be methylated on oxygen, or on carbon to give isomer (9) exclusively.
R. McCague, C. J. Moody and C. W. Rees, J. Chem. Soc., Chem. Commun., 1982, 622 DOI: 10.1039/C39820000622
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