t-butyl hydroperoxide oxidative dealkylation of hydroquinone ethers to 1,4-quinones

Various organoselenium compounds (diselenides, benzisoselenazol-3(2H)-ones, and 1,3,2-thiaselenazolones) are effective catalysts for oxidative dealkylation of hydroquinone ethers with t -butyl hydroperoxide to 1,4-quinones. The reactions is most efficient when t -butyl hydroperoxide in the presence of poly(bis-1,2-phenyl) diselenide is used as an oxidizing agent. In this way 1,4-benzo and 1,4-naphthoquinones are produced in good to high yields.