Advertisement

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

Nitration of 5-formyl-substituted 2-cyclopropylfurans and 2-methylfurans and the corresponding thiophenes

  • 71 Accesses

  • 4 Citations

Abstract

In the nitration of 5-formyl-substituted 2-cyclopropylfurans and the corresponding thiophenes, in addition to the formation of the corresponding 3-nitro derivative the replacement of the formyl group by a nitro group takes place. For a thiophene derivative the latter direction of the reaction is observed to a substantially smaller degree. Under nitration conditions, 5-formylsylvane is converted only into 5-nitrosylvane, while the corresponding formylmethylthiophene is nitrated exclusively in position 3. The difference observed in the behavior on nitration of the furans and thiophenes studied is explained by the different degrees of participation of the heteroatom in the delocalization of the charges in the heterocyclic ipso-ions formed as intermediates.

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

Literature cited

  1. 1.

    R. M. Kellogg and J. Buter, J. Org. Chem.,36, 2236 (1971).

  2. 2.

    E. Ya. Lukevits, Advances in Furan Chemistry [in Russian], Zinatne, Riga (1978).

  3. 3.

    L. I. Belen'kii, New Directions in Thiophene Chemistry [in Russian], Nauka, Moscow (1976).

  4. 4.

    K. Yu. Novitskii, V. P. Volkov, Yu. M. Il'ina, and Yu. K. Yur'ev, Zh. Obshch. Khim.,33, 1145 (1963).

  5. 5.

    I. Burdon, G. E. Chivers, and I. C. Tatlow, J. Org. Chem., 729 (1955).

  6. 6.

    Yu. S. Shabarov, S. S. Mochalov, and I. P. Stepanova, Dokl. Akad. Nauk SSSR,189, 1028 (1969).

  7. 7.

    Yu. K. Yur'ev and D. Ekkkhardt, Zh. Obshch. Khim.,31, 3274 (1961).

  8. 8.

    N. M. Kizhner, Zh. Russ. Fiz.-Khim. Ova.,61, 781 (1929).

  9. 9.

    V. A. Zefirova and R. A. Karakhanov, Khim. Geterotsikl. Soedin., No. 8, 1032 (1977).

  10. 10.

    R. A. Karakhanov, V. A. Zefirova, and T. I. Snoval'nikova, Khim. Geterotsikl. Soedin., No. 12, 1591 (1972).

  11. 11.

    A. Fischer and I. N. Ramsay, Can. J. Chem.,52, 3960 (1974).

  12. 12.

    Yu. S. Shabarov, S. S. Mochalov, N. B. Matveeva, and I. P. Stepanova, Zh. Org. Khim.,11, 568 (1975).

  13. 13.

    S. S. Mochalov, V. I. Daineko, N. F. Balan, and Yu. S. Shabarov, Dokl. Akad. Nauk SSSR,238, 1105 (1978).

  14. 14.

    Yu. S. Shabarov, S. S. Mochalov, and V. I. Daineko, Zh. Org. Khim.,12, 1293 (1976).

  15. 15.

    Yu. S. Shabarov, S. S. Mochalov, and S. A. Ermishkina, Dokl. Akad. Nauk SSSR,211, 1135 (1973).

  16. 16.

    S. S. Mochalov, S. A. Ermishkina, S. K. Erglis, and Yu. S. Shabarov, Zh. Org. Khim.,11, 1409 (1975).

  17. 17.

    A. Hinz, G. Meyer, and G. Schucking, Ber.,76, 676 (1943).

  18. 18.

    V. Reichstein, Helv. Chim. Acta,13, 346 (1930).

  19. 19.

    W. I. Keng, J. Org. Chem.,13, 635 (1948).

Download references

Author information

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 455–460, April, 1980.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Mochalov, S.S., Abdel'razek, F.M., Surikova, T.P. et al. Nitration of 5-formyl-substituted 2-cyclopropylfurans and 2-methylfurans and the corresponding thiophenes. Chem Heterocycl Compd 16, 339–344 (1980). https://doi.org/10.1007/BF00552770

Download citation

Keywords

  • Nitrate
  • Organic Chemistry
  • Thiophene
  • Furan
  • Nitration