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Oxidative Triflamidation of Allyl Cyanide in Nitrile Solutions

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Abstract

The reaction of triflamide with allyl cyanide in benzonitrile and isobutyronitrile solutions in the presence of NBS has been studied. In both cases, the corresponding amidines formed by solvent insetion were obtained. In benzonitrile, depending on the reaction conditions, the isomeric N-(2-bromo-3-cyanopropyl)-N'-(triflyl)benzamidine and N-(1-bromo-3-cyanoprop-2-yl)-N'-(triflyl)benzamidine were obtained in various ratios. The reaction in isobutyronitrile resulted in the isolation of N-(2-bromo-3-cyanopropyl)-N'-(triflyl)isobutyramidine and the deamination product N-[3-cyano-1-(triflamido)propyl]isobutyramide.

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ACKNOWLEDGMENTS

The work was performed using the equipment of the Baikal Analytical Center for Collective Use, Siberian Branch, Russian Academy of Sciences.

Funding

The work was financially supported by the Russian Science Foundation (project no. 22-13-00036).

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Authors and Affiliations

  1. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    A. S. Ganin, M. M. Sobyanina, M. Yu. Moskalik & B. A. Shainyan

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  1. A. S. Ganin
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  2. M. M. Sobyanina
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  3. M. Yu. Moskalik
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  4. B. A. Shainyan
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Correspondence to A. S. Ganin.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1410–1417 https://doi.org/10.31857/S0514749223110022.

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Ganin, A.S., Sobyanina, M.M., Moskalik, M.Y. et al. Oxidative Triflamidation of Allyl Cyanide in Nitrile Solutions. Russ J Org Chem 59, 1851–1857 (2023). https://doi.org/10.1134/S1070428023110027

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  • DOI: https://doi.org/10.1134/S1070428023110027

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