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Keto–enol tautomerization

4 real reactions from the literature, on enols, phenols and aryl ketones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Keto–enol tautomerization: hydroxy-1-cyclohexene-1-carboxylic acid (an enol) with H2O gives 2-oxocyclohexanecarboxylic acid (the tautomer).
    Keto–enol tautomerizationJ. Am. Chem. Soc. 2003, 125, 6478

  2. Keto–enol tautomerization: an enol with MeOH; 65 °C gives the tautomer. 68% yield.
    Keto–enol tautomerizationJ. Am. Chem. Soc. 1968, 90, 1367

  3. Keto–enol tautomerization: 1,4-naphthalenediol (a phenol) with TFA gives 2,3-dihydro-1,4-naphthoquinone (the tautomer).
    Keto–enol tautomerizationAngew. Chem. Int. Ed. 2006, 45, 98

  4. Keto–enol tautomerization: anthrone (an aryl ketone) with AcOH gives anthranol (the tautomer).
    Keto–enol tautomerizationJ. Chem. Soc., Perkin Trans. 2 2002, 784