Abstract
A new type of easily dimerized heterocyclic compound, viz., nitro derivatives of 2-phenylpyrrolo[1,2-a]benzimidazole, was discovered. The reaction proceeds by heating the latter in acetic acid. A radical mechanism for the dimerization that takes into account partial protonation of the starting compound is discussed on the basis of electrochemical data, the high π-donor capacity of 2-phenyl-4-methylpyrrolo[1,2-a]benzimidazole, the coloration that is characteristic for selfcomplexes, and EPR spectroscopy.
Similar content being viewed by others
Literature cited
A. I. Shakhnovich, B. V. Salov, and M. V. Gorelik, Khim. Geterotsikl. Soedin., No. 12, 1636 (1978).
Ya. Ya. Dregeris and Ya. F. Freimanis, Zh. Vses. Khim. Ova., No. 5, 496 (1978).
J. Kolc and J. Michl, J. Am. Chem. Soc., 95, 7391 (1973).
T. A. Kuz'menko, V. V. Kuz'menko, A. M. Simonov, M. S. Korobov, and S. A. Fillppov, Khim. Geterotsikl. Soedin., No. 3, 388 (1982).
A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 9, 1155 (1979).
A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 6, 723 (1977).
A. N. Kost, M. A. Yurovskaya, and A. S. Vyazgin, Khim. Geterotsikl. Soedin., No. 9, 1222 (1980).
P. B. Kurapov and N. A. Klyuev, Khim. Geterotsikl. Soedin., No. 9, 1237 (1979).
L. M. Alekseeva, G. G. Dvoryantseva, I. V. Persianova, Yu. N. Sheinker, R. M. Palei, and L. M. Kochergin, Khim. Geterotsikl. Soedin., No. 8, 1132 (1972).
M. Yu. Kornilov, G. G. Dyadyusha, and F. S. Babichev, Khim. Geterotsikl. Soedin., No. 5, 905 (1968).
V. A. Anisimova, N. I. Avdyunina, A. F. Pozharskii, A. M. Simonov, and L. N. Talanova, Khim. Geterotsikl. Soedin., No. 4, 528 (1980).
R. L. Hinman and E. R. Shull, J. Org. Chem., 26, 2339 (1961).
G. E. Troshin, F. F. Lakomov, and I. M. Sosonkin, Elektrokhimiya, 17, 894 (1981).
S. G. Mairanovskii, N. P. Rodionov, and V. P. Gul'tyai, Zavod. Lab., 40, 518 (1974).
R. M. Palei and P. M. Kochergin, Khim. Geterotsikl. Soedin., No. 3, 536 (1967).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 188–196, February, 1984.
Rights and permissions
About this article
Cite this article
Pozharskii, A.F., Kuz'menko, T.A., Kuz'menko, V.V. et al. Dimerization of biradicaloid heterocyclic compounds. Nitro derivatives of pyrrolo[1, 2-a]benzimidazole. Chem Heterocycl Compd 20, 150–159 (1984). https://doi.org/10.1007/BF00506284
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00506284