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Ethynylation of cycloaliphatic ketones

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

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%.

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Literature cited

  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).

  2. D. Papa, F. Vilani, and H. Ginsberg, Arch. Biochem. Biophys.,33, 482 (1951); J. Amer. Chem. Soc.,76, 4446 (1954).

    Google Scholar 

  3. T. Takeshima, K. Wakamatsu, and A. Furuhashi, Bull. Chem. Soc., Japan, 33, 640 (1958).

    Google Scholar 

  4. A. A. Petrov, Zh. obshch. khimii,11, 309 (1941); K. Aider and W. Vogt, Ann.,564, 109 (1949).

    Google Scholar 

  5. I. N. Nazarov, G. P. Kugatova, and G. A. Laumyanskas, Zh. obshch. khimii,27, 2450 (1957).

    Google Scholar 

  6. G. P. Kugatova-Shemyakina and Yu. A. Ovchinnikov, Tetrahedron,18, 697 (1962).

    Google Scholar 

  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. Organic Syntheses [Russian translation] (1953),4, p. 82; T. Takeshima, J. Scient. Res. Inst.,48, 103 (1954).

  9. A. A. Petrov and N. P. Sopov, Zh. obshch. khimii,22, 591 (1952).

    Google Scholar 

  10. P. Sabatier and A. Mailhe, Compt. rend.,139, 345 (1904).

    Google Scholar 

  11. N. Sharma and S. Dumt, J. Indian, Chem. Soc.,12, 774, 1935 (1953).

    Google Scholar 

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Author information

Authors and Affiliations

  1. Institute for the Chemistry of Natural Products, Academy of Sciences, USSR

    D. A. Kazlauskas & G. P. Kugatova-Shemyakina

  2. Institute of Chemistry and Chemical Technology, Academy of Sciences, Lithuanian SSR

    D. A. Kazlauskas & G. P. Kugatova-Shemyakina

Authors
  1. D. A. Kazlauskas
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  2. G. P. Kugatova-Shemyakina
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Additional information

This article is published in accordance with a resolution of the Conference of Chief Editors of Journals of the Academy of Sciences of the USSR of July 12, 1962, as a dissertation paper by D. A. Kazlauskas.

The authors thank L. B. Senyavina for determining the infrared spectra.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 95–103, January, 1965

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Kazlauskas, D.A., Kugatova-Shemyakina, G.P. Ethynylation of cycloaliphatic ketones. Russ Chem Bull 14, 82–89 (1965). https://doi.org/10.1007/BF00854865

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  • DOI: https://doi.org/10.1007/BF00854865

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