Chemistry of Halonitroethenes,
Part 2: Trichloronitroethene as a Building Block for the Novel Synthesis
of 5-Chloro(nitro)methyl-Substituted 1-Aryltetrazoles

Viktor A. Zapol’skii; Xuena Yang; Jan C. Namyslo; Mimoza Gjikaj; Dieter E. Kaufmann

doi:10.1055/s-0031-1289716

PAPER

Chemistry of Halonitroethenes, Part 2: Trichloronitroethene as a Building Block for the Novel Synthesis of 5-Chloro(nitro)methyl-Substituted 1-Aryltetrazoles

Viktor A. Zapol’skii^a, Xuena Yang^a, Jan C. Namyslo^a, Mimoza Gjikaj^b, Dieter E. Kaufmann*^a
^a Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstraße 6, 38678 Clausthal-Zellerfeld, Germany
Fax: +49(5323)722834; e-Mail: dieter.kaufmann@tu-clausthal.de;
^b Institute of Inorganic and Analytical Chemistry, Clausthal University of Technology, Paul-Ernst-Straße 4, 38678 Clausthal-Zellerfeld, Germany

Abstract

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Abstract

Conversion of 1,1,2-trichloro-2-nitroethene with an excess of 1H-benzotriazole, followed by transamination of the resulting 1,1-bis(benzotriazol-1-yl)-2-chloro-2-nitroethene with different aniline derivatives provides the corresponding 1-(arylimino)-1-(benzotriazolyl)ethanes. Upon cycloaddition with sodium azide, these amidines enable the formation of hitherto unknown 1-aryltetrazoles bearing a chloro(nitro)methyl group in the 5-position. The structure of a 4-fluorophenyl derivative was proven by single-crystal X-ray diffraction analysis. Starting from arenediamines, this reaction affords bistetrazoles. In addition, the tetrazoles are interesting starting materials for further conversions of the side chain.

Key words

nitro compounds - nucleophilic substitution - amidines - arenes - heterocycles - tetrazoles

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References

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