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Oxidative nucleophilic substitution of hydrogen in nitroarenes by silyl enol ethers

✍ Scribed by Mieczysław Mąkosza; Marek Surowiec

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
158 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

Enolates generated by treatment of silyl ketene acetals and enol ethers with fluoride ion sources add to nitroarenes to produce s H adducts that oxidize either with KMnO 4 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 s H adducts via O-silylation but due to the nature of the accompanying cation.

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Oxidative nucleophilic substitution of h
Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetonitrile derivatives
✍ Mieczyslaw Ma̧kosza; Krzysztof Staliński 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 836 KB

Tertiary carbanions generated from a-substituted phenylacetonitriles in liquid ammonia add to nitrobenzenes in the para position to form the corresponding oH-adducts which are transformed, depending on the starting nitriles and the reaction conditions, to products of oxidative nucleophilic substitut