Heating the phenolic iodide (14) with potassium t-butoxide and t-butyl alcohol in a sealed tube gave the phenolic dienone (6) or the adamantanoid dienone (18a) depending on the quantity of potassium t-butoxide used. Treatment of (18a) with DDQ gives the adamantanoid bis-dienone (17), which fails to undergo the dienone–phenol rearrangement in the presence of trifluoracetic acid.
R. S. Atkinson and J. E. Miller, J. Chem. Soc., Perkin Trans. 1, 1979, 3017 DOI: 10.1039/P19790003017
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