Conclusions
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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.
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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
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.
M. F. Shostakovskii and A. V. Bogdanova, Diacetylene Chemistry [in Russian], Nauka (1971), p. 196.
A. V. Bogdanova, G. P. Kugatova-Shemyakina, A. N. Volkov, and B. G. Arkelyan, Izv. Akad. Nauk SSSR, Ser. Khim.1964, 174.
I. I. Nazarova, B. N. Gusev, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim.,1967, 1580.
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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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DOI: https://doi.org/10.1007/BF00924568