Abstract
The nitration of 4-(5-R-2-thienyl)-3-buten-2-ones with nitric acid in acetic anhydride is accompanied by the formation of a mixture of nitro isomers, whereas nitration with nitric acid and copper and aluminum nitrates in carbon tetrachloride, dichloroethane, and acetonitrile leads to the production of only the α-nitro ketone. The results of quantum-chemical calculations of the reactivity indexes within the CNDO/2 approximation are in agreement with the experimental data on electrophilic substitution of these compounds in the basic and protonated forms.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
L. V. Panfilova, M. Yu. Antipin, Yu. D. Churkin, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., No. 9, 120] (1979).
J. A. Pople and G. A. Segal, J. Chem. Phys., 44, 3289 (1966).
D. P. Sautry and G. A. Segal, J. Chem. Phys., 47, 158 (1967).
G. Gombes, M. Hebbelynck, and I. Ledrut, Bull. Soc. Chim. Fr., No. 3, 315 (1953).
A. V. Topchiev, in: Selected Works. Nitration [in Russian], Nauka, Moscow (1965), p. 55.
H. Gilman (editor), Organic Syntheses [Russian translation], Vol. 1, Inostr. Lit., Moscow (1949), p. 76.
Yu. D. Churkin and L. V. Panfilov, Khim. Geterotsikl. Soedin., No. 8, 1048 (1980).
Author information
Authors and Affiliations
Additional information
See [1] for Communication 1.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 325–328, March, 1981.
Rights and permissions
About this article
Cite this article
Churkin, Y.D., Panfilova, L.V., Shashkov, A.S. et al. Nitro derivatives of the thiophene series. 2. Nitration of thienyl-substituted unsaturated methyl ketones. Chem Heterocycl Compd 17, 232–235 (1981). https://doi.org/10.1007/BF00505983
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00505983