Evidence for carbon-carbon Meisenheimer-Wheland complexes between superelectrophilic and supernucleophilic carbon reagents

被引:57
作者
Boga, C [1 ]
Del Vecchio, E [1 ]
Forlani, L [1 ]
Mazzanti, A [1 ]
Todesco, PE [1 ]
机构
[1] Univ Bologna, Fac Chim Ind, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
关键词
carbanions; carbocations; electrophilic addition; nucleophilic addition; zwitterions;
D O I
10.1002/anie.200500238
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) 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). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3285 / 3289
页数:5
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