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Cyclic unsaturated compounds

Communication 33. New method for the synthesis of indan
  • V. A. Mironov
  • A. P. Ivanov
  • A. A. Akhrem
Organic and Biological Chemistry
  • 15 Downloads

Conclusions

  1. 1.

    A study was made of the transformations of spiro [4.4]-1, 3-nonadiene (I), an equilibrium mixture of bicyclo[4.3.0]-1, 3-nonadiene (II), bicyclo[4.3.0]-2, 4-nonadiene (III) and bicyclo [4.3.0]-1(5), 3-nonadiene (IV), and also bicyclo[4.3.0]-1, 5-nonadiene (V), in the presence of palladium-on-carbon in the temperature range 120–400°.

     
  2. 2.

    Under the experimental conditions, dienes (I)–(V) are converted in good yields to indan (VI) as the result of three consecutive reactions (I) → (II)+(III)+(IV) → V) → (VI).

     
  3. 3.

    A convenient method was developed for the synthesis of indan (VI) by the catalytic isomerization-dehydrogenation of the readily available spiro [4.4]-1, 3-nonadiene (I).

     

Keywords

Indan Diene Good Yield Spiro Convenient Method 
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.

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Literature cited

  1. 1.
    V. A. Mironov, A. P. Ivanov, Ya. M. Kimel'fel'd, L. I. Petrovskaya, and A. A. Akhrem, Izv. Akad. Nauk SSSR, Ser. Khim., 2571 (1970).Google Scholar
  2. 2.
    L. Gatterman, Ann. Chem.,347, 384 (1906).Google Scholar
  3. 3.
    V. Jacobi, J. Prakt. Chem.,129, 55 (1931).Google Scholar
  4. 4.
    J. von Braun, Z. Arkuszewski, and Z. Köhler, Chem. Ber.,51, 291 (1918).Google Scholar
  5. 5.
    W. Borsche and M. Pommer, Chem. Ber.,54, 102 (1921).Google Scholar
  6. 6.
    I. A. Musaev and G. D. Gal'pern, Zh. Prikl. Khim.,12, 572 (1938).Google Scholar
  7. 7.
    W. M. Kutz, J. E. Nickels, J. J. McGovern, and B. B. Corson, J. Am. Chem. Soc.,70, 4026 (1948).Google Scholar
  8. 8.
    N. D. Zelinsky and I. N. Titz, Chem. Ber., 2869 (1929).Google Scholar
  9. 9.
    K. D. Errington and R. P. Lenstead. J. Chem. Soc., 666 (1938).Google Scholar
  10. 10.
    H. Adkins, L. M. Richards, and J. W. Davis, J. Am. Chem. Soc.,63, 1320 (1941).Google Scholar
  11. 11.
    E. Clemmensen, Chem. Ber.,47, 682 (1914).Google Scholar
  12. 12.
    R. F. Nystrom, C. Rainer, and A. Berger, J. Am. Chem. Soc.,80, 2896 (1958).Google Scholar
  13. 13.
    F. Fichter and H. Stenzl, Helv. Chim. Acta,22, 425 (1939).Google Scholar
  14. 14.
    A. T. Blomquist, J. Wolinsky, Y. C. Meinwald, and D. T. Longone, J. Am. Chem. Soc.,78, 6057 (1956).Google Scholar
  15. 15.
    C. M. Suter and G. A. Lutz, J. Am. Chem. Soc.,60, 1360 (1938).Google Scholar
  16. 16.
    S. I. Khromov, E. S. Balenkova, O. E. Lishenok, and B. A. Kazanskii, Dokl. Akad. Nauk SSSR,135, 627 (1960).Google Scholar
  17. 17.
    A. L. Liberman, O. V. Bragin, and B. A. Kazanskii, Dokl. Akad. Nauk SSSR,111, 1039 (1965).Google Scholar
  18. 18.
    O. V. Bragin, G. K. Gur'yanova, and A. L. Liberman, Dokl. Akad. Nauk SSSR,160, 823 (1965).Google Scholar
  19. 19.
    E. S. Balenkova, N. A. Khafizova, M. L. Frank, S. I. Khromov, and B. A. Kazanskii, Dokl. Akad. Nauk SSSR,158, 1112 (1964).Google Scholar
  20. 20.
    B. A. Kazanskii, S. I. Khromov, A. L. Liberman, E. S. Balenkova, T. V. Vasina, V. T. Aleksan-yan, and Kh. E. Sterin, Dokl. Akad. Nauk SSSR,135, 327 (1960).Google Scholar
  21. 21.
    G. G. Eberhardt, J. Org. Chem.,29, 643 (1964).Google Scholar
  22. 22.
    I. P. Losev, O. S. Smirnova, and T. A. Pfeifer, Zh. Obshch. Khim.,21, 668 (1951).Google Scholar
  23. 23.
    USA Patent No. 2535606 (1950); C. A.,45, 7784 (1951).Google Scholar
  24. 24.
    R. Mecke and F. Langenbucher, Catalog of Infrared Spectra of Selected Chemical Compounds, Heyden and Son, Ltd., London (1965), p. 945.Google Scholar
  25. 25.
    V. A. Mironov, A. P. Ivanov, and A. A. Akhrem, USSR Patent No. 263591 (1969).Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • V. A. Mironov
    • 1
  • A. P. Ivanov
    • 1
  • A. A. Akhrem
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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