Selective Oxidation of Benzylic Alcohols and Ethers and Oxidative Cleavage of Benzylic Tetrahydropyranyl and Trimethylsilyl Ethers to Their Carbonyl Compounds by Dinitrogen Tetroxide–Impregnated Activated Charcoal (N₂O₄/Charcoal)

Abstract

Benzylic alcohols and ethers were oxidized to their corresponding carbonyl compounds using dinitrogen tetroxide impregnated on activated charcoal (N₂O₄/charcoal) in CH₂Cl₂ at room temperature. Efficient oxidative cleavage of trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to their corresponding carbonyl compounds was also performed by this reagent. High selectivity was observed for oxidation of benzylic alcohols and ethers and also trimethylsilyl ethers in the presence of tetrahydropyranyl ethers.

Keywords:

• Benzylic alcohol
• benzylic ether
• charcoal
• oxidation
• tetrahydropyranyl ether
• trimethylsilyl ether
• N₂O₄

Acknowledgment

The authors are thankful to Shiraz University Research Council for the partial support of this work.