Advertisement

Chemistry of Heterocyclic Compounds

, Volume 8, Issue 4, pp 424–427 | Cite as

Investigation of selenides of the thiophene and furan series

VII. Cleavage of some aryl hetaryl selenides BY n-butyllithium or bromine
  • V. P. Litvinov
  • A. N. Sukiasyan
  • Ya. L. Gol'dfarb
Article

Abstract

As in the case of alkyl 2-thienyl selenides, replacement of the alkylseleno group to form the corresponding lithium derivative is observed when n-butyllithium acts on alkyl 2-furyl and alkyl 2-selenienyl selenides. The alkylselenide function is also replaced when alkyl 2-thienyl selenides are treated with excess bromine. A scheme of the mechanism for the reaction of alkyl 2-hetaryl selenides with n-butyllithium is proposed. Alkyl 2-furyl selenides undergo the diene synthesis with maleic anhydride to give phthalic anhydride without a selenide function as the final product.

Keywords

Lithium Organic Chemistry Anhydride Diene Bromine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    V. S. Bogdanov, V. P. Litvinov, A. N. Sukiasyan, and Ya. L. Gol'dfarb, Zh. Organ. Khim., 7, 1257 (1971).Google Scholar
  2. 2.
    Ya. L. Gol'dfarb, V. P. Litvinov, and A. N. Sukiasyan, Izv. Akad. Nauk SSSR, Ser. Khim.,2585 (1967).Google Scholar
  3. 3.
    Ya. L. Gol'dfarb, V. P. Litvinov, and A. N. Sukiasyan, Dokl. Akad. Nauk SSSR, 182, 340 (1968).Google Scholar
  4. 4.
    H. Gilman and F. J. Webb, J. Am. Chem. Soc., 71, 4062 (1949).Google Scholar
  5. 5.
    H. Gilman and R. L. Bebb, J. Am. Chem. Soc., 61, 109 (1939).Google Scholar
  6. 6.
    D. A. Shirley and R. J. Reeves, J. Organomet. Chem., 16, 1 (1969).Google Scholar
  7. 7.
    A. N. Sukiasyan, V. P. Litivinov, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., 1345 (1970).Google Scholar
  8. 8.
    Ya. L. Gol'dfarb, V. P. Litvinov, and A. N. Sukiasyan, Izv. Akad. Nauk SSSR, Ser. Khim., 1296 (1971).Google Scholar
  9. 9.
    L. I. Belen'kii, N. S. Ksenzhek, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., 310 (1972).Google Scholar
  10. 10.
    O. K. Edwards, W. R, Gaytwaite, J. Kenyon, and H. Phillips, J. Chem. Soc., 2293 (1928).Google Scholar
  11. 11.
    P. Spinoglio and M. De Gasperi, Gazz. Chim. Ital., 67, 318 (1937).Google Scholar
  12. 12.
    E. Hannig and H. Ziebandt, Pharmazie, 23, 552 (1968).Google Scholar
  13. 13.
    Ya. L. Gol'dfarb, Ya. L. Danyushchevskii, and M. A. Marakatkina, USSR Author's Certificate No. 187,778 (1965); Byull. Izobr., No. 21, 39 (1966).Google Scholar
  14. 14.
    Ya. L. Danyushevskii, M. A. Marakatkina, and Ya. L. Gol'dfarb, Zh. Organ. Khim., 4, 474 (1968).Google Scholar
  15. 15.
    L. Chugaev, Ber., 42, 53 (1909).Google Scholar
  16. 16.
    Syntheses of Heterocyclic Compounds [in Russian], Vol. 1, Izd. Akad. Nauk Arm. SSSR, Erevan (1956), p. 54.Google Scholar
  17. 17.
    E. G. Kataev and M. F. Palkina, Uch. Zap. Kazansk. Univ., 113, 115 (1953).Google Scholar
  18. 18.
    G. Ayrey, D. Barnard, and D. T. Woodbridge, J. Chem. Soc., 2095 (1962).Google Scholar
  19. 19.
    M. Nardelli and L. Chierici, Ann. Chim. (Rome), 42, 111 (1952); Chem. Abstr., 47, 7454 (1952).Google Scholar
  20. 20.
    H. D. Hartough, Thiophene and Its Derivatives, New York (1952), p. 208.Google Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • V. P. Litvinov
    • 1
  • A. N. Sukiasyan
    • 1
  • Ya. L. Gol'dfarb
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations