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)
- 1 June 2005
- journal article
- Published by Taylor & Francis Ltd in Synthetic Communications
- Vol. 35 (11), 1527-1533
- https://doi.org/10.1081/scc-200058001
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
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