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Abstract— The mechanisms by which 4‐substituted 2,6‐di‐t‐butylphenols are oxygenated by base‐ and Co(II) Schiff base complex‐catalysis into o‐ or p‐peroxyquinols and their Co(III) complexes, respectively, have been investigated. For the base‐catalyzed oxygenation, a one‐step ionic mechanism involving no radical species is suggested to be the most probable one. For the formation of the peroxycobalt(III) complexes, the following stoichiometry is concluded: ArOH + Co(II) + 5/4 O2→ peroxycobalt(III) complex + 1/2 H2O. A mechanism involving an electron transfer between the phenols and the Co(II)‐O2 complex followed by further electron transfer between the formed phenoxy radicals and the Co(II) complex to give the corresponding phenolate anions is proposed.