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Adamantylation of N-aryl and N-arylalkyl acetamides in trifluoroacetic acid

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Abstract

Alkylation of N-aryl and N-arylalkyl acetamides with hydroxy adamantane derivatives in trifluoroacetic acid was studied. The differentiating effect of trifluoroacetic acid on the regio-selectivity of adamantylation of o-alkyl-substituted acetanilides was established, leading to energetically more stable products of para-substitution with respect to the alkyl group (the content of para-alkyl isomers is 93–94%). This enabled the synthesis of adamantylaminoarenes in 83–99% yields and with 95–99% purity.

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Authors and Affiliations

  1. Volgograd State Technical University, 28 prosp. Lenina, 400005, Volgograd, Russian Federation

    I. A. Novakov, B. S. Orlinson, D. V. Zavyalov, V. I. Porkhun, E. N. Savelyev, E. A. Potaenkova, O. V. Vostrikova, M. A. Nakhod, A. V. Kireeva & A. M. Pichugin

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  1. I. A. Novakov
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  2. B. S. Orlinson
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  3. D. V. Zavyalov
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  4. V. I. Porkhun
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  5. E. N. Savelyev
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  6. E. A. Potaenkova
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  7. O. V. Vostrikova
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  8. M. A. Nakhod
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  9. A. V. Kireeva
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  10. A. M. Pichugin
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Corresponding author

Correspondence to E. A. Potaenkova.

Additional information

Dedicated to the Academician of the Russian Academy of Sciences I. L. Eremenko on the occasion of his 70th birthday.

This study was carried out using equipment of the Center for Collective Use “Physicochemical Investigation Methods” of the Volgograd State Technical University.

This study was financially supported by the Ministry of Higher Education and Science of the Russian Federation (state assignment No. 4.3230.2017/4.6).

Published in Russian in Izyestiya Akcademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1096–1101, June, 2020.

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Novakov, I.A., Orlinson, B.S., Zavyalov, D.V. et al. Adamantylation of N-aryl and N-arylalkyl acetamides in trifluoroacetic acid. Russ Chem Bull 69, 1096–1101 (2020). https://doi.org/10.1007/s11172-020-2873-9

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  • DOI: https://doi.org/10.1007/s11172-020-2873-9

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