Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Reactions of aromatic and heteroaromatic compounds, bearing electron-acceptor substituents

Communication 17. Direction of bromination and relative activity of the complexes of some aldehydes and ketones of the furan and thiophene series with aluminum chloride and protic acids

  • 36 Accesses

  • 5 Citations

Conclusions

  1. 1.

    On the example of brominating the AlCl3 complex of 2-acetylfuran it was shown that the 4 position in this complex is more active than the 5 position.

  2. 2.

    The deactivating effect of the acyl group, bound in the AlCl3 complex, is transmitted better through the furan ring than through the thiophene ring. As a result the reactivity of the AlCl3 complexes of carbonyl compounds of the furan series during bromination is lower than that of the corresponding complexes of the thiophene analogs, whereas the reverse ratio of the activities is true for the free carbonyl compounds.

  3. 3.

    The direction of the bromination of the protonated 2-thiophenecarboxaldehyde and 2-acetothienone (complexes with HSbCl6) differs but slightly from that of the corresponding complexes with AlCl3

This is a preview of subscription content, log in to check access.

Literature cited

  1. 1.

    Ya. L. Gol'dfarb, N. S. Ksenzhek, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim.,1161 (1973).

  2. 2.

    L. I. Belen'kii, G. P. Gromova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin.,597 (1972).

  3. 3.

    L. I. Belen'kii, I. B. Karmanova, G. P. Gromova, É. I. Novikova, Ya. L. Gol'dfarb, V. S. Bogdanov, and L. V. Shmelev, Zh. Organ. Khim.,9, 1499 (1973).

  4. 4.

    Ya. L. Gol'dfarb, É. I. Novikova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim.,2841 (1971).

  5. 5.

    S. Clementi, P. Linda, and G. Marino, J. Chenu Soc.,B1971, 79.

  6. 6.

    L. I. Belen'kii, G. P. Gromova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin.,591 (1972).

  7. 7.

    F. Fringuelli, G. Marino, and A. Taticchi, J. Chem. Soc., Perkin II,1738 (1972).

  8. 8.

    B. Rcques, S. Combrisson, C. Riche, and C. Pascard-Billy, Tetrahedron,26, 3555 (1970).

  9. 9.

    S. Granowitz, Arkiv Kemi,8, 87 (1955).

  10. 10.

    Ya. I. Gol'dfarb, V. P. Litvinov, and V. I. Shvedov, Zh. Obshch. Khim.,30, 534 (1960).

  11. 11.

    L. I. Belen'kii, G. P. Gromova, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim.,1228 (1971).

  12. 12.

    Ya. L. Gol'dfarb and L. D. Tarasova, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk,1304 (1960).

  13. 13.

    Ya. L. Gol'dfarb and L. D. Tarasova, Dokl. Akad. Nauk SSSR,163, 1393 (1965).

  14. 14.

    Ya. L. Gol'dfarb, M. A. Marakatkina, and L. I. Belen'kii, Khim. Geterotsikl. Soedin.,132 (1970).

  15. 15.

    S. G. Mairanovskii, N. V. Kondratova, I. B. Karmanova, and Yu. B. Vol'kenshtein, Izv. Akad, Nauk SSSR, Ser. Khim.,2429 (1971).

  16. 16.

    Ya. L. Gol'dfarb, Yu. B. Vol'kenshtein, and B. V. Lopatin, Zh. Obshch. Khim.,34, 969 (1964).

Download references

Author information

Additional information

See [1] for Communication 16.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2733–2739, December, 1973.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Belen'kii, L.I., Gol'dfarb, Y.L. & Gromova, G.P. Reactions of aromatic and heteroaromatic compounds, bearing electron-acceptor substituents. Russ Chem Bull 22, 2666–2671 (1973). https://doi.org/10.1007/BF00926134

Download citation

Keywords

  • Carbonyl
  • Thiophene
  • Furan
  • AlCl3
  • Carbonyl Compound