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28.1.3.1.1 Method 1: Oxidative Dearomatization

DOI: 10.1055/sos-SD-028-00057

Kim, S. H.; Theodorakis, E. A.Science of Synthesis, (20062854.

Oxidative dearomatization is the most efficient way to prepare hydroxy- or alkoxy-substituted benzo-1,4-quinones. Corresponding precursors are phenols, hydroquinones, and hydroquinone mono- and diethers. A variety of metals, including cobaltsalen complex, Fremy's salt, chromium trioxide, ammonium cerium(IV) nitrate, lead(IV) oxide, diphenylseleninic anhydride, and copper(II)/oxygen have been used to accomplish this oxidation. The choice of experimental conditions and product yield depend upon the steric and electronic effects of the starting materials. In general, oxidative dearomatization of hydroquinones proceeds under milder conditions than those required for phenol oxidation; thus the former dearomatization is preferred for sensitive substrates. In addition, ortho oxidation of phenols constitutes the main side reaction producing the corresponding benzo-1,2-quinones.[‌4‌]

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