Chemistry of Heterocyclic Compounds

, Volume 17, Issue 7, pp 673–675

Nitro derivatives of the thiophene series. 4. Nitration of thiophene derivatives with metal nitrates in acetic anhydride


  • Yu. D. Churkin
    • V. V. Kuibyshev Kuibyshev Polytechnic Institute
  • L. V. Panfilova
    • V. V. Kuibyshev Kuibyshev Polytechnic Institute
  • V. D. Lugovoi
    • V. V. Kuibyshev Kuibyshev Polytechnic Institute
  • N. V. Boiko
    • V. V. Kuibyshev Kuibyshev Polytechnic Institute

DOI: 10.1007/BF00506032

Cite this article as:
Churkin, Y.D., Panfilova, L.V., Lugovoi, V.D. et al. Chem Heterocycl Compd (1981) 17: 673. doi:10.1007/BF00506032


The nitration of 2-formylthiophene, 2-acetothienone, and unsaturated ketones of the thiophene series with copper and aluminum nitrates in acetic anhydride at various temperatures was studied. At low temperatures 2-acetothienone gives a mixture of 4- and 5-nitro isomers, while 2-formylthipphene gives only a 5-nitro-substituted compound in the diacetate form; α,β-unsaturated ketones are not nitrated under these conditions. When the reaction is carried out at 70–90 °C, one can obtain mixtures of nitro ketones in the case of unsaturated ketones; 2-formylthiophene is oxidized to thiophene-2-carboxylic acid, while 2-acetothienone gives a substance, the structure of which could not be established. The reaction of copper and aluminum nitrates with acetic anhydride was investigated by means of thermal and x-ray diffraction analysis. It is shown that the reaction is accompanied by the formation of free nitric acid, and the nitrating agent in these mixtures is consequently the nitronium cation.

Copyright information

© Plenum Publishing Corporation 1982