Abstract
Classical polarography inaprotic solvents was used to study the reduction of N-vinyl derivatives of pyrazole, imidazole, 1,2,3- and 1,2,4-triazoles, and tetra-zole. The N-vinylazoles studied were reduced in acetonitrile by a one-electron mechanism with subsequent dimerization of the radical-anions formed. The N-vinyl derivatives of pyrazole, imidazole and tetrazole were reduced analogously in DMF, while N-vinyltriazoles in DMF are reduced by a mixed mechanism with predominant two-electron transfer. Possible schemes for the electrochemical reduction of N-vinylazoles are discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
L. A. Korshikov, A. P. Karpinets, and V. D. Bezuglyi, Elecktrokhimiya, 10, 990 (1974).
V. D. Bezuglyi, A. P. Karpinets, and L. A. Korshikov, Elektrokhimiya, 11, 1253 (1975).
G. S. Shapoval, T. E. Lipatova, and E. S. Shevchuk, Vysokomol. Soedin., 20A, 2104 (1978).
V. D. Bezuglyi and Yu. Ponomarev, Zh. Anal. Khim., 20, 505 (1965).
T. G. Ermakova, A. I. Gritsa, N. M. Deriglazov, L. A. Tatarova, V. V. Keiko, T. I. Vakul'skaya, and V. A. Lopyrev, Khim. Geterotsikl. Soedin., No. 3, 408 (1980).
V. A. Lopyrev, T. N. Kashik, L. E. Protasova, T. G. Ermakova, and M. G. Voronkov, Vysokomol. Soedin., 26B, 594 (1984).
C. Mann and K. Barnes, Electrochemical Reactions in Nonaqueous Systems [Russian translation], Izd. Khimiya, Moscow (1974), p. 15.
V. N. Kizhnyaev, V. A. Kruglova, L. E. Protasova, G. V. Ratovskii, G. A. Gareev, and L. I. Vereshchagin, Vysokomol. Soedin., 28A, (1986) (in print).
S. G. Mairanovskii, Ya. P. Stradyn', and V. D. Bezuglyi, Polarography in Organic Chemistry [in Russian], Izd. Khimiya, Moscow (1975), p. 68.
I. P. Grandberg and G. I. Sharova, Khim. Geterotsikl. Soedin., No. 6, 1097 (1968).
M. F. Shostakovskii, G. C. Skvortsova, N. P. Glazkova, and E. S. Domnina, Khim. Geterotsikl. Soedin., No. 9, 1279 (1981).
V. A. Lopyrev, N. P. Kuznetsova, G. F. Myachina, ad T. G. Ermakova, Khim. Geterotsikl. Soedin., No. 11, 1535 (1983).
L. P. Makhno, T. G. Ermakova, E. S. Domnina, L. A. Tatarova, G. G. Skvortsova, and V. A. Lopyrev, USSR Inventor's Certificate No. 464, 584; Byul. Izobr., No. 4, 66 (1975).
B. I. Mikhat'ev, G. V. Shatalov, and V. D. Galkin, in: Monomers and High-Molecular-Weight Compounds [in Russian], Voronezh (1973), p. 87.
G. G. Skvortsova, E. S. Domnina, N. P. Glazkova, and L. P. Makhno, Abstracts of the Third All-Union Conference on Acetylene Chemistry [in Russian], Izd. Nauka, Moscow (1972), p. 115.
S. R. Buzilova, V. M. Shul'gina, G. V. Sakovich, and L. I. Vereshchagin, Khim. Geterotsikl. Soedin., No. 9, 1279 (1981).
C. Mann, The Electrochemistry of Metals in Nonaqueous Solutions [Russian translation], Izd. Mir, Moscow (1974), p. 17.
W. Reppe and E. Keyssner, German Patent No. 618, 120; Chem. Abst., 30, 110 (1936).
S. Trofimenko, J. Org. Chem., 24, 3459 (1970).
W. G. Finnegan and R. A. Henry, J. Org. Chem., 24, 1565 (1959).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 315–319, March, 1986.
Rights and permissions
About this article
Cite this article
Lopyrev, V.A., Ermakova, T.G., Kashik, T.N. et al. Electrochemical reduction of N-vinylazoles. Chem Heterocycl Compd 22, 253–257 (1986). https://doi.org/10.1007/BF00514989
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00514989