Direct Observation of the Intermediate in Vicarious Nucleophilic Substitutions of Hydrogen

Direct Observation of the Intermediate in Vicarious Nucleophilic Substitutions of Hydrogen

Mononitrobenzene derivatives and 1‐chloro‐1‐arylsulfonyl‐methyl anions react with formation of stable σH adducts (see scheme; Ts=tosyl) which are observed by UV/Vis and NMR spectroscopy. The generally accepted energy profiles for vicarious nucleophilic substitutions with σH adducts as high‐energy in...

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Veröffentlicht in:Angewandte Chemie International Edition 2003-06, Vol.42 (24), p.2793-2795
Hauptverfasser: Lemek, Tadeusz, Mąkosza, Mieczysław, Stephenson, David S., Mayr, Herbert
Format: Artikel
Sprache:eng
Schlagworte:
aromatic substitution
carbanions
elimination
kinetics
nucleophilic substitution
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Beschreibung
Zusammenfassung:Mononitrobenzene derivatives and 1‐chloro‐1‐arylsulfonyl‐methyl anions react with formation of stable σH adducts (see scheme; Ts=tosyl) which are observed by UV/Vis and NMR spectroscopy. The generally accepted energy profiles for vicarious nucleophilic substitutions with σH adducts as high‐energy intermediates have to be revised.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351352