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Synthesis of β-diketones and acetylenic ketones from ethers of tertiary diacetylenic alcohols

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Conclusions

  1. 1.

    To prevent the formation of dihydrofurans when diacetylenic carbinols are hydrated it is recommended to replace the alcohols by either their ethers or esters.

  2. 2.

    Depending on the reaction conditions, the hydration of the ethers of tertiary diacetylenic carbinols can be directed toward the formation of either theβ-diketones or acetylenic ketones.

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Literature cited

  1. 1.

    S. I. Shergina, I. E. Sokolov, A. S. Zanina, and I. L. Kotlyarevskii, Papers Delivered at All-Union Conference on Acetylene Chemistry [in Russian], Vol. 2, Alma-Ata (1972), p. 217.

  2. 2.

    M. F. Shostakovskii and A. V. Bogdanova, Diacetylene Chemistry [in Russian], Nauka (1971), p. 196.

  3. 3.

    A. V. Bogdanova, G. P. Kugatova-Shemyakina, A. N. Volkov, and B. G. Arkelyan, Izv. Akad. Nauk SSSR, Ser. Khim.1964, 174.

  4. 4.

    I. I. Nazarova, B. N. Gusev, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim.,1967, 1580.

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2781–2784, December, 1977.

The authors thank L. Ya. Al'ta for assistance in taking and interpreting the NMR spectra.

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Zanina, A.S., Shergina, S.I., Khabibulina, G.N. et al. Synthesis of β-diketones and acetylenic ketones from ethers of tertiary diacetylenic alcohols. Russ Chem Bull 26, 2572–2575 (1977). https://doi.org/10.1007/BF00924568

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Keywords

  • Alcohol
  • Ether
  • Ester
  • Hydrate
  • Ketone