t‐Butyl Hydroperoxide Oxidative Dealkylation of Hydroquinone Ethers to 1,4‐Quinones

Abstract

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.

Keywords:

• t‐Butyl hydroperoxide
• 1,4‐dimethoxyarenes
• hydroquinone ethers
• organoselenium compounds
• oxidation

Acknowledgments

This work was supported by the Polish State Committee for Scientific Research (Grant No. 3T09A 003 27).