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2,3-Epoxyperfluoro-2-methylpentane in reactions with urea and thiourea

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Abstract

2,3-Epoxyperfluoro-2-methylpentane reacts with thiourea in protic (methanol, 2-propanol) and aprotic (dioxane) solvents, and also with urea in acetonitrile affording unexpected products: 1-(2,2,3,3,3-pentafluoropropionyl)-2-(2,2,2-trifluoro-1-trifluoro-methylethyl)isothiourea, and 1-(2,2,3,3,3-pentafluoropropionyl)-3-(2,2,2-trifluoro-1-trifluoro-methylethyl)urea respectively that result from the rearrangement of the intermediately formed ketone in the process of the intramolecular “haloform” cleavage. At the same time in dioxane the 2,3-epoxyperfluoro-2-methylpentane reacts with urea with the formation of a heterocyclic compound, 2-amino-4-pentafluoroethyl-5,5-bis(trifluoromethyl)-4,5-dihydrooxazol-4-ol. From 1-(2,2,3,3,3-pentafluoropropionyl)-2-(2,2,2-trifluoro-1-trifluoromethylethyl)isothiourea and Cu(OAc)2 a stable fluorine-containing chelate complex was obtained.

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Authors and Affiliations

  1. Postovskii Institute of Organic Chemistry, Ural Branch, Russian Academy of Sciences, Yekaterinburg, 620990, Russia

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

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

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Dedicated to Academician of the Russian Academy of Sciences V.N. Charushin on occasion of his 60th anniversary

Original Russian Text © T.I. Filyakova, L.V. Saloutina, A.Ya. Zapevalov, P A. Slepukhin, M.I. Kodess, V.I. Saloutin, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 5, pp. 649–657.

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Filyakova, T.I., Saloutina, L.V., Zapevalov, A.Y. et al. 2,3-Epoxyperfluoro-2-methylpentane in reactions with urea and thiourea. Russ J Org Chem 47, 650–658 (2011). https://doi.org/10.1134/S107042801105022

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  • DOI: https://doi.org/10.1134/S107042801105022

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