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Ethynylation of cycloaliphatic ketones

  • D. A. Kazlauskas
  • G. P. Kugatova-Shemyakina
Organic and Biological Chemistry
  • 72 Downloads

Summary

  1. 1.

    The ethynylation of cycloaliphatic ketones was studied. With sodium acetylide,3-cyclohexen-1-ylketones condense rather worse than the corresponding cyclohexyl ketones do.

     
  2. 2.

    In their condensation with lithium acetylide cyclohexyl, 3-cyclohexen-1-yl, and 1-cyclohexen-1-yl ketones form tertiary acetylenic alcohols with equal ease in yields of 70–80%.

     

Keywords

Sodium Alcohol Lithium Ketone Cyclohexyl 
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.
    A. W. Johnson, The Chemistry of the Acetylenic Compounds,1, The Acetylenic Alcohols, L. Arnold and Co. (1946); W, Oroshnik and A. D. Mebane, J. Amer. Chem. Soc.,71, 2062 (1949); J. R. Boisier, Prod, pharmac.,11, 237, 319 (1956); W. Chodkiewicz, Theses pour obtenir le titre de docteurs de L'Université, Paris (1958).Google Scholar
  2. 2.
    D. Papa, F. Vilani, and H. Ginsberg, Arch. Biochem. Biophys.,33, 482 (1951); J. Amer. Chem. Soc.,76, 4446 (1954).Google Scholar
  3. 3.
    T. Takeshima, K. Wakamatsu, and A. Furuhashi, Bull. Chem. Soc., Japan, 33, 640 (1958).Google Scholar
  4. 4.
    A. A. Petrov, Zh. obshch. khimii,11, 309 (1941); K. Aider and W. Vogt, Ann.,564, 109 (1949).Google Scholar
  5. 5.
    I. N. Nazarov, G. P. Kugatova, and G. A. Laumyanskas, Zh. obshch. khimii,27, 2450 (1957).Google Scholar
  6. 6.
    G. P. Kugatova-Shemyakina and Yu. A. Ovchinnikov, Tetrahedron,18, 697 (1962).Google Scholar
  7. 7.
    G. P. Kugatova-Shemyakina, G. A. Laumyanskas, G. K. Krasil'nikova, and V. I. Vidugirene, Zh. obshch. khimii,32, 49 (1962).Google Scholar
  8. 8.
    Organic Syntheses [Russian translation] (1953),4, p. 82; T. Takeshima, J. Scient. Res. Inst.,48, 103 (1954).Google Scholar
  9. 9.
    A. A. Petrov and N. P. Sopov, Zh. obshch. khimii,22, 591 (1952).Google Scholar
  10. 10.
    P. Sabatier and A. Mailhe, Compt. rend.,139, 345 (1904).Google Scholar
  11. 11.
    N. Sharma and S. Dumt, J. Indian, Chem. Soc.,12, 774, 1935 (1953).Google Scholar

Copyright information

© Consultants Bureau Enterprises Inc. 1965

Authors and Affiliations

  • D. A. Kazlauskas
    • 1
    • 2
  • G. P. Kugatova-Shemyakina
    • 1
    • 2
  1. 1.Institute for the Chemistry of Natural ProductsAcademy of SciencesUSSR
  2. 2.Institute of Chemistry and Chemical TechnologyAcademy of SciencesLithuanian SSR

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