Evidence for Carbon-Carbon Meisenheimer-Wheland Complexes between Superelectrophilic and Supernucleophilic Carbon Reagents

Proposal accepted: NMR experiments have shown unequivocally that the previously only proposed zwitterionic carbon–carbon Meisenheimer–Wheland complexes are formed in the reaction of 4,6‐dinitrobenzofuroxan (DNBF) with 1,3,5‐tris(N,N‐dialkylamino)benzenes. Increasing the temperature results in a rapi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-05, Vol.44 (21), p.3285-3289
Main Authors: Boga, Carla, Del Vecchio, Erminia, Forlani, Luciano, Mazzanti, Andrea, Todesco, Paolo E.
Format: Article
Language:English
Subjects:
carbanions
carbocations
electrophilic addition
nucleophilic addition
zwitterions
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Summary:Proposal accepted: NMR experiments have shown unequivocally that the previously only proposed zwitterionic carbon–carbon Meisenheimer–Wheland complexes are formed in the reaction of 4,6‐dinitrobenzofuroxan (DNBF) with 1,3,5‐tris(N,N‐dialkylamino)benzenes. Increasing the temperature results in a rapid exchange between three homomeric forms of the complex (see scheme; NR2=piperidyl, morpholinyl, pyrrolidinyl).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200500238