Abstract
It was established that 5-bromo-2-cyclopropylthiophene and 5-methyl-2-cyclo-propylthiophene undergo transformations during nitration with nitric acid in acetic anhydride that are a consequence of ipso attack of the nitryl cation in the 2 or 5 positions of the thiophene rings of the starting compounds.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. Fischer and J. N. Ramsay, Can. J. Chem., 52, 3960 (1974).
S. S. Mochalov, N. B. Matveeva, I. P. Stepanova, and Yu. S. Shabarov, Zh. Org. Khim., 13, 1639 (1977).
P. Cogolli, F. Maiolo, L. Testaferri, M. Tiecco, and M. Tingoli, J. Heterocycl. Chem., 16, 1495 (1979).
S. S. Mochalov, F. M. Abdel'razek, T. P. Surikova, and Yu. S. Shabarov, Khim. Geterotsikl. Soedin., No. 4, 455 (1980).
S. S. Mochalov, V. V. Karpova, and Yu. S. Shabarov, Zh. Org. Khim., 16, 571 (1980).
R. B. Moodie, K. Schofield, and S. B. Weston, J. Chem. Soc., Perkin II, No. 9, 1089 (1976).
Yu. S. Shabarov, S. S. Mochalov, N. B. Matveeva, and I. P. Stepanova, Zh. Org. Khim., 11, 568 (1975).
Yu. S. Shabarov and S. S. Mochalov, Zh. Org. Khim., 8, 293 (1972).
S. Nichimura, A. Sakumoto, and E. Imoto, Nippon Kagaku Zasshi, 82, 1540 (1961); Chem. Abstr., 57, 15051 (1962).
Yu. S. Shabarov and S. S. Mochalov, Zh. Org. Khim., 9, 2044 (1973).
R. M. Kellogg and J. Buter, J. Org. Chem., 36, 2236 (1971).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 189–194, February, 1981.
Rights and permissions
About this article
Cite this article
Mochalov, S.S., Surikova, T.P., Abdel'razek, F.M. et al. Ipso attack in the nitration of 5-bromo- and 5-methyl-2-cyclopropylthiophenes. Chem Heterocycl Compd 17, 132–136 (1981). https://doi.org/10.1007/BF00507242
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00507242