Abstract: In the oxygenation of 4-alkyl-2, 6-di-tert-butylphenols (1) catalyzed by potassium tert-butoxide, molecular oxygen is added to the phenolates regioselectively depending on the solvent. In aprotic solvents the para position of the phenolates is oxygenated exclusively, and the resulting p-hydroperoxy anion intermediates (5') are converted to the corresponding epoxy-p-qui-nols (2). In tert-butyl alcohol, the ortho position is oxygenated predominantly, ...
