2-Alkyl-1,2,3,4-benzotetrazinium Tetrafluoroborates: Their Reaction with Nucleophiles

2-Alkyl-1,2,3,4-benzotetrazinium Tetrafluoroborates: Their Reaction with Nucleophiles

Treatment of 2‐alkyl‐1,2,3,4‐benzotetrazinium tetrafluoroborates with a nucleophile (AlkO−, ArO−, AcO−, Hal−, CN−, NCO−, ArNH2, AlkNH2, Alk2NH), at room temperature, results in elimination of an N2 molecule to afford ortho‐substituted azobenzenes. This reaction could be suitable for mild phenylation...

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Veröffentlicht in:European journal of organic chemistry 2004-12, Vol.2004 (23), p.4794-4801
Hauptverfasser: Lipilin, Dmitry L., Smirnov, Oleg Y., Churakov, Aleksandr M., Strelenko, Yuri A., Tyurin, Aleksei Y., Ioffe, Sema L., Tartakovsky, Vladimir A.
Format: Artikel
Sprache:eng
Schlagworte:
Aromatic substitution
Azo compounds
Fused-ring systems
Nitrogen heterocycles
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Zusammenfassung:Treatment of 2‐alkyl‐1,2,3,4‐benzotetrazinium tetrafluoroborates with a nucleophile (AlkO−, ArO−, AcO−, Hal−, CN−, NCO−, ArNH2, AlkNH2, Alk2NH), at room temperature, results in elimination of an N2 molecule to afford ortho‐substituted azobenzenes. This reaction could be suitable for mild phenylation of carboxylic acids and other compounds containing active hydrogen. A plausible reaction pathway for the reaction is discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400588