The interaction of 1,4-dyhydroxynaphthalene with tertiary alcohols in trifluoroacetic acid was investigated. It was shown, that alkylation occurred in position 2 with formation of 2-(tert.alkyl)-2,3-dihydronaphthalene-1,4-diones. Kinetic of keto-enol tautomerization 2-(1-adamantyl)-2,3-dihydronaphthalene-1,4-dione into 2-(1-adamantyl)-1,4-dyhydroxynaphthalene by morpholine action was analyzed using ¹H NMR spectroscopy.   2-(1-adamantyl)-1,4-dyhydroxynaphthalene was quickly oxidized into 2-(1-adamantyl)-1,4-naphthoquinone by atmospheric oxygen.