Acceleration of bromide mediated benzoylperoxide oxidations of secondary alcohols in aqueous organic solvents |
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Authors: | Jennessa Ji Youn Youm Matthias Bierenstiel |
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Affiliation: | a University of Guelph, Department of Chemistry, Guelph, Ontario, Canada N1E 2W1 b Cape Breton University, Department of Chemistry, Sydney, Nova Scotia, Canada B1P 6L2 |
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Abstract: | The efficiency of the bromide mediated benzoylperoxide oxidation of 2° alcohols to ketones was greatly improved by the addition of water. The aqueous oxidation protocol allows also the direct use of off-the-shelf benzoylperoxide reagent without an otherwise necessary and potentially dangerous drying procedure. The oxidation of cyclopentanol, cyclohexanol, 1-phenyl-ethanol and three menthol isomers occurred in good to excellent yields. The oxidation reaction tolerated N,N-dimethylacetamide (DMA) as the solvent, which resulted in a slightly lower oxidation rate than acetonitrile. Chemoselective oxidation of vicinal diols to α-hydroxy ketones did not succeed under the aqueous organic conditions employed as over-oxidation and bromination side-reactions were observed. The impact of water content, solvent, oxidant source and type of alcohol substrates employed was investigated. |
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Keywords: | Hypobromous acid Benzoyl hypobromite Selective oxidation Mechanistic studies Vicinal diol |
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