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Reactions of methyl esters of adamantane acids with acetonitrile

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Abstract

Methyl adamantane-1-carboxylate and methyl (1-adamantyl)acetate react with acetonitrile in the presence of sodium hydride to give 3-(1-adamantyl)-3-oxopropanenitrile and 4-(1-adamantyl)-3-oxobutanenitrile, respectively. Reaction involving methyl (1-adamantyl)-acetate produces also 2-(1-adamantyl)-N-(E-1-cyanoprop-1-ene-2-yl)acetamide; the structure of this side product was established by X-ray diffraction analysis.

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Authors and Affiliations

  1. Samara State Technical University, 244 ul. Molodogvardeiskaya, 443100, Samara, Russian Federation

    A. K. Shiryaev, R. S. Belen´kaya, V. A. Shiryaev & Yu. N. Klimochkin

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, 3 Build., 1 Leninskie Gory, 119991, Moscow, Russian Federation

    V. B. Rybakov

Authors
  1. A. K. Shiryaev
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  2. R. S. Belen´kaya
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  3. V. A. Shiryaev
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  4. V. B. Rybakov
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  5. Yu. N. Klimochkin
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Corresponding author

Correspondence to A. K. Shiryaev.

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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2966—2969, December, 2015.

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Shiryaev, A.K., Belen´kaya, R.S., Shiryaev, V.A. et al. Reactions of methyl esters of adamantane acids with acetonitrile. Russ Chem Bull 64, 2966–2969 (2015). https://doi.org/10.1007/s11172-015-1256-0

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  • DOI: https://doi.org/10.1007/s11172-015-1256-0

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