Skip to main content
SpringerLink
Log in

Synthesis of steroid compounds and related substances Communication XVII. Preparation ofa,β-unsaturated cyclic ketones (2-cycloalken-1-ones)

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    A general method has been developed for the preparation ofa,β-unsaturated cyclic ketones. There are two stages: bromination of a cyclic ketone in presence of calcium or magnesium carbonate; and elimination of hydrogen bromide from the bromo ketone formed, which is effected by heating it in presence of diethylaniline.

  2. 2.

    2-Methyl-2-cyclohexen-1-one (58% yield), 2-methyl-2-cyclopenten-1-one (50% yield), 2-cyclohexen-1-one (35% yield), and 2-cyclopentea-1-one (25% yield) have been prepared by this method.

  3. 3.

    It has been proved that, in the bromination of 2-methylpyclohexanone and of 2-methylcyclopentanone, bromine attacks the tertiary carbon atom, and not a secondary carbon, as assured previously by some workers.

  4. 4.

    The method of preparing 2,4-dimethyl-2-cyclopenten-1-one has been simplified and improved.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. I. N. Nazarov, et al, J. Gen. Chem., 20, 648, (1950); I. N. Nazarov, et, al., J. Gen. Chem., 20, 661, (1950); 20, 876 (1950).

    Google Scholar 

  2. I. N. Nazarov and I. I. Zaretskaya, Bull. Acad. Sci. USSR, Div. Chem. Sci., No, 1, 65 (1944).

  3. A. Koetz, et al, Ann. 358, 196 (1908); 379, 10 (1911); 400, 73 (1913).

    Google Scholar 

  4. A. Birch, J. Chem. Soc., 1944, 430; 1946, 593,

  5. P. Bartlett, M. Woods, J. Am. Chem. Soc., 62, 2933 (1940).

    Google Scholar 

  6. W. Rigby, J. Chem. Soc., 1949, 1586.

  7. L. Butz, A. Caddis, J. Org. Chem., 12, 121 (1947).

    Google Scholar 

  8. A. Koetz, Scharnhorst, Ann., 379, 10 (1911).

    Google Scholar 

  9. M. Mousseron, R. Richaud and R. Granger, Bull., 625 (1946); see also M. Godchot and M. Mousseron, Comptes. rend., 200, 2189 (1933).

  10. E. Dane, et al, Ann., 532, 29 (1937).

    Google Scholar 

  11. J. Rinkes, Rec., 57, 176 (1938); C. A. 32, 3345 (1938).

    Google Scholar 

  12. E. Dane, et al, Ann., 539, 210 (1939).

    Google Scholar 

  13. O. Wallach, Ann., 359, 303 (1908). F. Whitmore, G. Pedlow, J. Am. Chem. Soc., 63, 758 (1941); M. Orchin, J. Am. Chem. Soc., 66, 537 (1944); M. Mousseron, R. Jacquier, F. Winternitz, Comptes. rend., 224, 1230 (1947).

    Google Scholar 

  14. O. Wallach, Ann., 359, 303 (1908).

    Google Scholar 

  15. A. E. Favorsky, J. Russ. Phys. Chem. Soc., 44, 1362 (1912).

    Google Scholar 

  16. A. Haller, R. Cornubert, Comptes. rend., 158, 298 (1914); M. Godchot, F. Taboury, Bull., (4), 13, 596 (1913).

    Google Scholar 

  17. Ya. I. Denisenko and A. D. Naber, Bull. Acad. Sci. USSR, Div. Chem. Sci., 35 (1945); Gregoire, Chiurdoglu, Bull., 527 (1950).

  18. A. E. Favorsky, J. Russ. Phys. Chem. Soc., 38, 741 (1906).

    Google Scholar 

  19. T. Vaughn, R. Vogt, J. Nieuwland, J. Am. Chem. Soc., 56, 2120 (1934).

    Google Scholar 

  20. A. Haller, R. Cornubert, Comptes. rend., 179, 315, 320 (1924); 180, 1989 (1925); Bull. (4). 39, 1724, 1729(1900

    Google Scholar 

  21. S. Best, J. Thorpe. Soc., 95, 712 (1909); Mellor, Soc., 79, 130 (1901).

    Google Scholar 

  22. G. Blanc, Comptes. rend., 144, 1357 (1907); Bull. (4), 3, 779 (1908).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry of the USSR Academy of Sciences, Russia

    I. N. Nazarov, L. D. Bergelson, I. V. Torgov & S. N. Ananchenko

Authors
  1. I. N. Nazarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. D. Bergelson
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. V. Torgov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. N. Ananchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nazarov, I.N., Bergelson, L.D., Torgov, I.V. et al. Synthesis of steroid compounds and related substances Communication XVII. Preparation ofa,β-unsaturated cyclic ketones (2-cycloalken-1-ones). Russ Chem Bull 2, 787–798 (1953). https://doi.org/10.1007/BF01178858

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01178858

Keywords

Search

Navigation