Free-radical oxidation of para-substituted phenols by hypervalent tert-butylperoxyiodane and tert-butyl hydroperoxide: Synthesis of 4-( tert-butylperoxy)-2,5-cyclohexadien-1-ones

Oxidation of 4-alkylphenols 1by 1-( tert-butylperoxy)-1,2-benziodoxol-3(1 H)-one ( 2) in the presence of tert-butyl hydroperoxide affords selectively 4-( tert-butylperoxy)-2,5-cyclohexadien-1-ones 3in good yields. Evidence for the involvement of free-radicals is reported.