First Evidence for Wheland Intermediates in Azo-Coupling Reactions − Reactions between 1,3,5-Tris(dialkylamino)benzene and Arenediazonium Salts

First Evidence for Wheland Intermediates in Azo-Coupling Reactions − Reactions between 1,3,5-Tris(dialkylamino)benzene and Arenediazonium Salts

We have investigated reactions between 1,3,5‐tris(1‐piperidyl)benzene and 1,3,5‐tris(4‐morpholinyl)benzene and 4‐substituted arenediazonium tetrafluoroborate salts, mainly by NMR spectroscopic measurements. The main products are σ complexes (Wheland‐like intermediates) which are formed in almost qua...

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Veröffentlicht in:European journal of organic chemistry 2004-04, Vol.2004 (7), p.1567-1571
Hauptverfasser: Boga, Carla, Del Vecchio, Erminia, Forlani, Luciano
Format: Artikel
Sprache:eng
Schlagworte:
Aromatic substitution
Diazo compounds
Electrophilic substitution
NMR spectroscopy
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Zusammenfassung:We have investigated reactions between 1,3,5‐tris(1‐piperidyl)benzene and 1,3,5‐tris(4‐morpholinyl)benzene and 4‐substituted arenediazonium tetrafluoroborate salts, mainly by NMR spectroscopic measurements. The main products are σ complexes (Wheland‐like intermediates) which are formed in almost quantitative yields and are moderately stable compounds. From these covalent complexes, products of the azo‐coupling reaction may be obtained as salts or as free bases. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300701