کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5281643 | 1385676 | 2008 | 5 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Acceleration of bromide mediated benzoylperoxide oxidations of secondary alcohols in aqueous organic solvents Acceleration of bromide mediated benzoylperoxide oxidations of secondary alcohols in aqueous organic solvents](/preview/png/5281643.png)
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.
The combination of commercially available wet benzoylperoxide with NiBr2 provides a fast and convenient oxidation reagent for 2° alcohols.
Journal: Tetrahedron Letters - Volume 49, Issue 20, 12 May 2008, Pages 3199-3203