Intramolecular condensation of nitro group with olefinic double bond

  • L. A. Simonyan
  • N. P. Gambaryan
  • P. V. Petrovskii
  • I. L. Knunyants
Organic and Biological Chemistry

Conclusions

A new reaction of nitro compounds was discovered on the example of the thermal isomerization of unsaturated nitrocarbinols and nitrodihydropyrans, consisting in the intramolecular addition of the nitro group to the olefinic double bond with the formation of the heterolytic 1,3,2-dioxazoline system.

Keywords

Double Bond Nitro Group Nitro Compound Thermal Isomerization Olefinic Double Bond 

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Literature cited

  1. 1.
    N. P. Gambaryan, El. M. Rokhlina, and Yu. V. Zeifman, Izv. Akad. Nauk SSSR, Ser. Khim.,1965, 1466.Google Scholar
  2. 2.
    T. R. Emerson and C. W. Rees, J. Chem. Soc.,1962, 1917.Google Scholar
  3. 3.
    G. W. Steinhoff and M. C. Henry, J. Organ. Chem.,29, 2808 (1964).Google Scholar
  4. 4.
    Y. Ahmad, M. S. Habib, Ziauddin Bashir, and Naz Bashir, Tetrahedron,21, 861 (1965).Google Scholar
  5. 5.
    E. Ochiai, J. Organ. Chem.,18, 534 (1953).Google Scholar
  6. 6.
    V. A. Tartakovskii, I. E. Chlenov, S. S. Smagin, and S. S. Novikov, Izv. Akad. Nauk SSSR, Ser. Khim.,1964, 583.Google Scholar
  7. 7.
    S. D. Sokolov and N. K. Kochetkov, Dokl. Akad. Nauk SSSR,156, 1391 (1964).Google Scholar
  8. 8.
    V. A. Tartakovskii, A. A. Onishchenko, I. E. Chlenov, and S. S. Novikov, Dokl. Akad. Nauk SSSR,164, 1081 (1965).Google Scholar
  9. 9.
    V. A. Tartakovskii, Dissertation [in Russian], Moscow (1966).Google Scholar
  10. 10.
    R. Huisgen, Angew. Chem.,75, 604, 742 (1963).Google Scholar
  11. 11.
    R. Grashey, Angew. Chem.,74, 155 (1962).Google Scholar
  12. 12.
    J. S. Splitter and M. Calvin, J. Organ. Chem.,20, 1086 (1955).Google Scholar
  13. 13.
    G. Buchi and D. E. Ayer, J. Amer. Chem. Soc.,78, 689 (1956).Google Scholar
  14. 14.
    M. L. Scheinbaum, J. Organ. Chem.,29, 2200 (1964).Google Scholar
  15. 15.
    K. L. McEwen, J. Chem. Phys.,32 (6), 1801 (1960).Google Scholar
  16. 16.
    J. Tanaka, J. Chem. Soc. Japan,78, 1643 (1957).Google Scholar
  17. 17.
    N. P. Gambaryan, L. A. Simonyan, and P. V. Petrovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1967, 918.Google Scholar
  18. 18.
    I. L. Knunyants, B. L. Dyatkin, and A. A. Gevorkyan, Izv. Akad. Nauk SSSR, Ser. Khim.,1966, 1377.Google Scholar
  19. 19.
    M. Martynoff, Bull. Soc. chim. France,1951, 214.Google Scholar
  20. 20.
    C. Mills, J. Chem. Soc.,67, 925 (1895).Google Scholar
  21. 21.
    F. Arndt, Ber.,46, 3522 (1913).Google Scholar
  22. 22.
    M. Colonna, Gazz. Chim. Ital,90, 1179 (1960).Google Scholar
  23. 23.
    R. W. Layer, Chem. Rev.,63, 489 (1963).Google Scholar
  24. 24.
    J. Hamer and A. Macaluso, Chem. Rev.,64, 473 (1964).Google Scholar
  25. 25.
    A. Hassner and D. R. Fitchmun, Tetrahedron Letters,1966, 1991.Google Scholar
  26. 26.
    G. Tennant, J. Chem. Soc.,1966, 2285.Google Scholar
  27. 27.
    J. P. Loudon and G. Tennant, Quart. Rev. (London),18, 389 (1964).Google Scholar
  28. 28.
    J. I. Brauman and V. A. Sanderson, Tetrahedron,23, 37 (1967).Google Scholar

Copyright information

© Consultants Bureau 1968

Authors and Affiliations

  • L. A. Simonyan
    • 1
  • N. P. Gambaryan
    • 1
  • P. V. Petrovskii
    • 1
  • I. L. Knunyants
    • 1
  1. 1.Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRUSSR

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