2,3-Epoxyperfluoro-2-methylpentane in reactions with urea and thiourea |
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| Authors: | T I Filyakova L V Saloutina A Ya Zapevalov P A Slepukhin M I Kodess V I Saloutin |
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| Institution: | 1.Postovskii Institute of Organic Chemistry, Ural Branch,Russian Academy of Sciences,Yekaterinburg,Russia |
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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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