Advertisement

Springer Nature is making Coronavirus research free. View research | View latest news | Sign up for updates

Investigation in the series of condensed heteroaromatic systems including a thiophene ring

Communication 20. Metallation of benzo-[b]-naphtho-[2,3-d]-thiophene and desulfurization of its alkyl derivatives

  • 18 Accesses

Conclusions

  1. 1.

    Under the action of n-butyllithium on benzo-[b]-naphtho-[2, 3-d]-thiophene (I), the lithium atom is inserted in the 4-position of the benzonaphthothiophene system.

  2. 2.

    In the desulfurization of 4- and 7-alkyl derivatives of benzonaphthothiophene (I) by Raney nickel, together with desulfurization there is a partial hydrogenation of the alkyl derivatives ofβ-phenylnaphthalene formed.

  3. 3.

    On the basis of a comparative study of the IR spectra of 4- and 7-alkyl derivatives of benzonaphthothiophene (I) and alkyl derivatives of naphthalenes, general principles in the vibrational spectra of these systems were found, which permitted a reliable confirmation of the position of the substituent in 4- and 7-alkyl derivatives of (I).

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

Literature cited

  1. 1.

    D. D. Gverdtsitel: and V. P. Litvinov, Soobshcheniya AN GSSR,59, 333 (1970).

  2. 2.

    H. Gilman and R. L. Bebb, J. Amer. Chem. Soc.,61, 109 (1939).

  3. 3.

    H. Gilman and D. A. Shirley, J. Amer. Chem. Soc.71, 1870 (1949).

  4. 4.

    D. A. Shirley and M. D. Cameron, J. Amer. Chem. Soc.,72, 2788 (1950);74, 664 (1952).

  5. 5.

    Ya. L. Gol'dfarb, S. A. Ozolin', and V. P. Litvinov, Zh. Obshch. Khim.,37, 2220 (1967).

  6. 6.

    H. Gilman, M. W. Van Ess, and H. B. Willisand, J. Amer. Chem. Soc.,62, 2606 (1940).

  7. 7.

    H. Gilman and C. G. Stuckwish, J. Amer. Chem. Soc.,67, 877 (1945).

  8. 8.

    J. D. Roberts and D. Y. Curtin, J. Amer. Chem. Soc.,68, 1658 (1946).

  9. 9.

    D. D. Gverdtsiteli and V. P. Litvinov, Izv. Akad. Nauk SSSR, Ser. Khim., 1340 (1970).

  10. 10.

    E. G. G. Werner, Recueil Trav. Chim.,68, 520 (1949).

  11. 11.

    G. Gilman, in: Organic Reactions [Russian translation], No. 8, IL (1956), p. 333.

  12. 12.

    N. Claverie, J. Chim. Phys.,60, 746 (1943).

  13. 13.

    A. L. McClellan and G. C. Pimetel, J. Chem. Phys.,23, 245 (1955).

  14. 14.

    E. R. Lippinkott and E. J. O'Reilly, J. Chem. Phys.,23, 238 (1955).

  15. 15.

    W. LeCalve-Claverie, Ann. Chimie,10, 5 (1965).

  16. 16.

    H. M. Fridman, Spectrochim. Acta.,22, 1465 (1966).

  17. 17.

    H. Hauptmann and W. F. Walter, Chem. Rev.,62, 347 (1962).

  18. 18.

    G. N. Kao, B. D. Tilak, and K. Venkataraman, Proc. Ind. Sci.,38A, 244 (1953).

  19. 19.

    W. Davies and Q. N. Porter, J. Chem. Soc., 459 (1957).

  20. 20.

    H. Hauptmann, W. F. Walter, and C. Marino, J. Amer. Chem. Soc.,80, 5832 (1958).

  21. 21.

    D. S. Tarbell and D. K. Fukushima, J. Amer. Chem. Soc.,68, 1456 (1946).

  22. 22.

    I. A. Ewidge and R. G. Foster, J. Chem. Soc., 981 (1964).

Download references

Author information

Additional information

For communication 19. see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 79–85, January, 1972.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Litvinov, V.P., Gverdtsiteli, D.D. & Lubuzh, E.D. Investigation in the series of condensed heteroaromatic systems including a thiophene ring. Russ Chem Bull 21, 70–75 (1972). https://doi.org/10.1007/BF00855658

Download citation

Keywords

  • Hydrogenation
  • Nickel
  • Lithium
  • Naphthalene
  • Thiophene