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Reactions of perfluoro(2,3-epoxy-2-methylpentane) with o-phenylenediamine and ethylenediamine

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Abstract

Perfluoro(2,3-epoxy-2-methylpentane) reacted with o-phenylenediamine and ethylenediamine via cleavage of the C-C bond to produce 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)-phenyl]propanamide and 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)ethyl]-propanamide, respectively. Presumably, these compounds are formed as a result of rearrangement of intermediate ketone generated by intramolecular haloform-type reaction. According to the NMR and X-ray diffraction data, 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)phenyl]propanamide in crystal exists as Z conformer with respect to the amide C-N bond.

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Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990, Russia

    T. I. Filyakova, A. Ya. Zapevalov, M. I. Kodess, P. A. Slepukhin & V. I. Saloutin

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  1. T. I. Filyakova
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  2. A. Ya. Zapevalov
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  3. M. I. Kodess
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  4. P. A. Slepukhin
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  5. V. I. Saloutin
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Correspondence to T. I. Filyakova.

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Dedicated to Full Member of the Russian Academy of Sciences I.P. Beletskaya on her jubilee

Original Russian Text © T.I. Filyakova, A.Ya. Zapevalov, M.I. Kodess, P.A. Slepukhin, V.I. Saloutin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 3, pp. 363–368.

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Filyakova, T.I., Zapevalov, A.Y., Kodess, M.I. et al. Reactions of perfluoro(2,3-epoxy-2-methylpentane) with o-phenylenediamine and ethylenediamine. Russ J Org Chem 49, 350–355 (2013). https://doi.org/10.1134/S1070428013030068

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  • DOI: https://doi.org/10.1134/S1070428013030068

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