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

2005; Wiley; Volume: 44; Issue: 21 Linguagem: Inglês

10.1002/anie.200500238

1521-3773

Carla Boga, Erminia Del Vecchio, Luciano Forlani, Andrea Mazzanti, P. E. TODESCO,

Molecular Spectroscopy and Structure

Angewandte Chemie International EditionVolume 44, Issue 21 p. 3285-3289 Communication Evidence for Carbon–Carbon Meisenheimer–Wheland Complexes between Superelectrophilic and Supernucleophilic Carbon Reagents† Carla Boga Dr., Carla Boga Dr. Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this authorErminia Del Vecchio Dr., Erminia Del Vecchio Dr. Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this authorLuciano Forlani Prof. Dr., Luciano Forlani Prof. Dr. forlani@ms.fci.unibo.it Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this authorAndrea Mazzanti Dr., Andrea Mazzanti Dr. Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this authorPaolo E. Todesco Prof. Dr., Paolo E. Todesco Prof. Dr. Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this author Carla Boga Dr., Carla Boga Dr. Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this authorErminia Del Vecchio Dr., Erminia Del Vecchio Dr. Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this authorLuciano Forlani Prof. Dr., Luciano Forlani Prof. Dr. forlani@ms.fci.unibo.it Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this authorAndrea Mazzanti Dr., Andrea Mazzanti Dr. Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this authorPaolo E. Todesco Prof. Dr., Paolo E. Todesco Prof. Dr. Dipartimento di Chimica Organica "A. Mangini", Facolta' di Chimica Industriale, Universita' di Bologna, Viale Risorgimento, 4-40136 Bologna, Italy, Fax: (+39) 051-209-3654Search for more papers by this author First published: 17 May 2005 https://doi.org/10.1002/anie.200500238Citations: 51 † This work was supported by the University of Bologna (ex 60 % MIUR and funds for selected research topics A.A. 2003–2004) and the Ministero dell'Università e della Ricerca Scientifica e Tecnologica. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract 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). Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z500238_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume44, Issue21May 20, 2005Pages 3285-3289 RelatedInformation