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Nucleophilic Replacement of Hydrogen in para-Substituted Nitrobenzenes by Phenylacetonitrile Carbanion

✍ Scribed by V. Yu. Orlov; Ya. V. Sokovikov; A. D. Kotov


Book ID
110335701
Publisher
SP MAIK Nauka/Interperiodica
Year
2002
Tongue
English
Weight
54 KB
Volume
38
Category
Article
ISSN
1070-4280

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ChemInform Abstract: Nucleophilic Substi
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## Abstract Stabilized carbanions of malonates, 2‐phenylacetonitrile, or isopropyl 2‐phenylacetate add to __m__‐(trichloromethyl)nitrobenzene derivatives to form σ^H^ adducts that lose a chloride ion to give intermediate __exo__‐dichloromethylene nitrocyclohexadienes. These undergo re‐aromatization

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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