Oxidative nucleophilic substitution of hydrogen in nitroarenes by silyl enol ethers |
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Authors: | Mieczys?aw M?kosza Marek Surowiec |
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Institution: | Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL-01-224 Warsaw, Poland |
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Abstract: | Enolates generated by treatment of silyl ketene acetals and enol ethers with fluoride ion sources add to nitroarenes to produce σH adducts that oxidize either with KMnO4 to give substituted nitroarenes or with dimethyldioxirane to give substituted phenols. In the latter case the oxidation results in replacement of the nitro group with a hydroxy group. It was shown that high effectiveness of these reactions is not due to stabilization of the σH adducts via O-silylation but due to the nature of the accompanying cation. |
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Keywords: | carbanions dimethyldioxirane nitroarenes oxidation phenols |
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