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Nitro derivatives of the thiophene series. 3. Study of the nitration of thiophene α,β-unsaturated ketones in the presence of protic and aprotic acids

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The nitration of 4-(5-R-2-thienyl) but-3-en-2-ones (R = H, CH3, C2H5) with a nitrating mixture and group I and III metal nitrates in concentrated sulfuric and trifluoroacetic acids, as well as in the presence of aluminum chloride, was investigated. Nitration with a nitrating mixture and potassium, sodium, lithium, copper, and aluminum nitrates in sulfuric acid takes place in the heterocyclic ring to give a mixture of nitro ketones. Nitration in trifluoroacetic acid and in the presence of aluminum chloride proceeds with the formation of a single α-nitro ketone. The structures of the substances obtained were proved by means of the IR and PMR spectra. A possible mechanism of the reaction is discussed.

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Authors and Affiliations

  1. V. V. Kuibyshev Kuibyshev Polytechnic Institute, 443645, Kuibyshev

    Yu. D. Churkin, L. V. Panfilova, A. S. Shashkov & K. Ya. Burshtein

Authors
  1. Yu. D. Churkin
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  2. L. V. Panfilova
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  3. A. S. Shashkov
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  4. K. Ya. Burshtein
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Additional information

See [1] for Communication 2.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 753–757, June, 1981.

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Churkin, Y.D., Panfilova, L.V., Shashkov, A.S. et al. Nitro derivatives of the thiophene series. 3. Study of the nitration of thiophene α,β-unsaturated ketones in the presence of protic and aprotic acids. Chem Heterocycl Compd 17, 549–552 (1981). https://doi.org/10.1007/BF00503477

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  • DOI: https://doi.org/10.1007/BF00503477

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