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Evidence for Carbon–Carbon Meisenheimer–Wheland Complexes between Superelectrophilic and Supernucleophilic Carbon Reagents
Author(s) -
Boga Carla,
Del Vecchio Erminia,
Forlani Luciano,
Mazzanti Andrea,
Todesco Paolo E.
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200500238
Subject(s) - chemistry , homomeric , carbon fibers , reagent , tris , reinforced carbon–carbon , medicinal chemistry , organic chemistry , computer science , gene , algorithm , biochemistry , composite number , protein subunit
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; NR 2 =piperidyl, morpholinyl, pyrrolidinyl).