Abstract
Reactions of azides and condensed tetrazoles, containing electropositive and electronegative substituents, with organomagnesium halogen compounds and organolithium compounds have been studied. The results obtained, like the study of the IR spectra carried out previously, permit the conclusion that the condensed tetrazoles are tautomeric compounds and the course of the reaction depends on the position of the azido-tetrazole equilibrium, which is affected by the nature of the substituent in the nitrogen-containing ring and the chemical nature of the reagent acting.
Similar content being viewed by others
References
O. Dimrot, M. Eble, and W. Gruhl, Ber.,40, 2390, 1907.
V. Ya. Pochinok, S. D. Zaitseva, and R. G. El'gort, Ukr. khim. zh.,17, 509, 1951.
V. Ya. Pochinok and S. D. Zaitseva, Ukr. khim. zh.,26, 351, 1960.
A. N. Nesmeyanov, V. N. Drozd, and V. A. Sazonova, DAN,150, 321, 1963.
H. Hoffman, Chem. Ber.,95, 2563, 1962.
V. Ya. Pochinok and L. F. Avramenko, Ukr. khim. zh.,28, 511, 1962.
L. F. Avramenko, V. Ya. Pochinok, and Yu. S. Rozum, ZhOKh,33, 980, 1963.
Yu. N. Sheinker, I. Ya. Postovskii, N. P. Bednyagina, L. B. Semyavina, and L. F. Lipatova, DAN,141, 1388, 1961.
I. Ya. Postovskii, N. P. Bednyagina, L. B. Semyavina, and Yu. N. Sheinker, Izv. AN SSSR, OFN,36, 1298, 1962.
I. Ya. Postovskii and I. N. Goncharova, ZhOKh,33, 2334, 1963.
I. Ya. Postovskii and N. B. Smirnova, DAN,166, 1136, 1966.
J. H. Boyer and E. J. Miller, J. Am. Chem. Soc.,81, 4671, 1959.
J. H. Boyer, M. S. Chang, and R. F. Reinisch, J. Org. Chem.,26, 286, 1960.
J. H. Boyer and H. W. Hyde, J. Org. Chem.,25, 458, 1960.
J. A. Reynolds and A. Van Allen, J. Org. Chem.,24, 1205, 1959.
H. Behringer and H. J. Fischer, Chem. Ber.,95, 2546, 1962.
C. Temple and J. A. Montgomery, J. Am. Chem. Soc.,86, 2946, 1964.
C. Temple and J. A. Montgomery, J. Org. Chem.,30, 826, 828, 1965.
C. Temple, M. C. Thorpe, W. C. Coburn, and J. A. Montgomery, J. Org. Chem.,31, 935, 1966.
W. Marekwalde and E. Meyer, Chem. Ber.,33, 1833, 1900.
R. Fargher and R. Furness, J. Chem. Soc.,107, 695, 1915.
V. Ya. Pochinok and S. D. Zaitseva, Ukr. khim. zh.,27, 675, 1961.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Skripnik, L.I., Pochinok, V.Y. Reactions of azides and condensed tetrazoles with organomagnesium halogen and organolithium compounds. Chem Heterocycl Compd 4, 353–355 (1968). https://doi.org/10.1007/BF00755279
Issue Date:
DOI: https://doi.org/10.1007/BF00755279