Chromium(VI) Oxide-Catalyzed Benzylic Oxidation with Periodic Acid

Shigekazu Yamazaki*

*Toyama Industrial Technology Center, 150 Futagami, Takaoka, Toyama 933-0981, Japan, Email: s-yamazkitc.pref.toyama.jp

S. Yamazaki, Org. Lett., 1999, 1, 2129-2132.

DOI: 10.1021/ol991175k

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Abstract

CrO₃ is an efficient catalyst for benzylic oxidation with periodic acid as the terminal oxidant in acetonitrile. Substituted electron-poor toluenes and diarylmethanes were oxidized to the corresponding substituted benzoic acids and ketones in excellent yields. Benzyl ethers such as isochroman and phthalan were converted to 3,4-dihydroisocoumarin and phthalide in quantitative yields.

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Key Words

chromium trioxide, periodic acid, ketones, esters

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ID: J54-Y1999