Abstract
The selective alkylation of mononuclear tetrazoles by 2,5-dimethyl-2,5-hexanediol and of N-unsubstituted binuclear tetrazoles by tert-butyl alcohol was realized in perchloric and sulfuric acids. A series of previously unknown N-substituted binuclear tetrazoles and tetrazolium salts were synthesized. Data from X-ray crystallographic analysis of 2,5-dimethyl-2,5-di(5-phenyl-2-tetrazolyl)hexane are presented.
Similar content being viewed by others
References
R. N. Butler,Comprehensive Heterocyclic Chemistry. II (Eds. A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Vol. 4, Pergamon Press, Oxford (1996), p. 621.
G. I. Koldobskii and V. A. Ostrovskii,Usp. Khim.,63, 847 (1994).
V. A. Ostrovskii and G. I. Koldobskii,Ross. Khim. Zh., No. 2, 84 (1997).
P. N. Gaponik,Chemical Problems of the Creation of New Materials and Technologies [in Russian] (Ed. V. V. Sviridov), Minsk (1998), p. 185.
A. J. Downard, P. J. Steel, and J. Steenwijk,Aust. J. Chem.,48, 1643 (1995).
C. Janiak, T. G. Scharmann, K. W. Brzezinka, and P. Reich,Chem. Ber.,128, 323 (1995).
R. W. Saalfrank, K. Schobert, S. Trummer, and A. Wolski,Z. Naturforsch.,50b, 642 (1995).
V. G. Kitaeva, D. T. Beresnev, R. I. Ishmetova, and G. L. Rusinov,Zh. Org. Khim.,31, 620 (1995).
V. I. Boev, E. M. Krasnikov, A. I. Moskalenko, E. I. Pil'ko, L. V. Snegur, V. N. Babin, and Yu. S. Nekrasov,Zh. Obshch. Khim.,67, 1386 (1997).
A. V. Sachivko, V. P. Tverdokhlebov, and I. V. Tselinskii,Ross. Khim. Zh., No. 2, 119 (1997).
S. A. Gromova, M. I. Barmin, I. B. Karaulova, A. N. Grebenkin, and V. V. Mel'nikov,Zh. Org. Khim.,34, 1094 (1998).
R. N. Butler and A. F. M. Fleming,J. Heterocycl. Chem.,34, 691 (1997).
J. Torres, J. L. Lavandera, P. Cabildo, R. M. Claramuni, and J. Elguero,J. Heterocycl. Chem.,25, 771 (1988).
A. O. Koren' and P. N. Gaponik,Khim. Geterotsikl. Soedin., No. 12, 1643 (1990).
A. O. Koren' and P. N. Gaponik,Khim. Geterotsikl. Soedin., No. 9, 1280 (1991).
S. V. Voitekhovich, P. N. Gaponik, and A. O. Koren,Mendeleev Commun., No. 1, 41 (1997).
P. N. Gaponik, S. V. Voitekhovich, A. S. Lyakhov, and I. I. Maruda,Khim. Geterotsikl. Soedin., No. 9, 1222 (1999).
P. N. Gaponik, S. V. Voitekhovich, I. I. Maruda, A. A. Kulak, and O. A. Ivashkevich,Pol. J. Chem.,72, 2247 (1998).
A. O. Koren, P. N. Gaponik, and V. A. Ostrovskii,Int. J. Chem. Kinet.,25, 1043 (1993).
A. O. Koren, P. N. Gaponik, O. A. Ivashkevich, and T. V. Kovalyova,Mendeleev Commun., No. 1, 10 (1995).
P. N. Gaponik and S. V. Voitekhovich,Zh. Org. Khim.,34, 788 (1998).
P. N. Gaponik, Yu. V. Grigor'ev, T. N. Andreeva, and I. I. Maruda,Khim. Geterotsikl. Soedin., No. 7, 915 (1995).
K. Yamaguchi, A. Ohsawa, T. Kaihoh, and T. Itoh,Acta Crystallogr.,C46, 1161 (1990).
Zi-yi Zhang and N. Zou,Chem. Research Chinese Univ.,10, 373 (1994).
F. H. Allen and O. Kennard,Chem. Design Automation News,8, 31 (1993).
W. G. Finnegan, R. A. Henry, and R. Lofqist,J. Am. Chem. Soc.,80, 3908 (1958).
P. N. Gaponik, V. P. Karavai, and Yu. V. Grigor'ev,Khim. Geterotsikl. Soedin., No. 11, 1521 (1985).
Yu. V. Grigor'ev, I. I. Maruda, and P. N. Gaponik,Vestsi AN Belarusi, No. 4, 80 (1997).
M. I. Ermakova, I. A. Shikhova, and N. I. Latosh,Zh. Obshch. Khim.,51, 174 (1981).
D. D. Coffman and E. L. Jenner,J. Am. Chem. Soc.,80, 2872 (1958).
G. M. Sheldrick,Program for Crystal Structure Refinement, Gottingen (1997).
G. M. Sheldrick,Acta Crystallogr.,A46, 467 (1990).
G. M. Sheldrick, Z. Dauter, K. S. Wilson, and L. Sieker,Acta Crystallogr.,D49, 18 (1993).
Additional information
Scientific-Research Institute of Physicochemical Problems, Belorus State University, Minsk; e-mail: fhp@fhp.bsu.unibel.by. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 387–395, March, 2000.
Rights and permissions
About this article
Cite this article
Gaponik, P.N., Voitekhovich, S.V. & Lyakhov, A.S. Selective synthesis of binuclear N-substituted tetrazoles and tetrazolium salts. Chem Heterocycl Compd 36, 326–333 (2000). https://doi.org/10.1007/BF02256871
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02256871