Reactions of internal perfluoroolefin oxides with urea |
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Authors: | L V Saloutina A Ya Zapevalov V I Saloutin M I Kodess P A Slepukhin |
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Institution: | (1) Postovskii Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620041, Russia |
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Abstract: | Internal perfluoroolefin oxides reacted with urea to give, depending on the solvent nature, two types of new fluorine-substituted nitrogen-containing heterocycles. 1,5-Bis(perfluoroalkyl)tetraazabicyclo3.3.0]octane-3,7-diones were formed in dimethyl sulfoxide, N,N-dimethylacetamide, and acetonitrile, while the reaction in dioxane resulted in the formation of unexpected products, 2-amino-5-fluoro-4,5-bis(perfluoroalkyl)-4,5-dihydrooxazol-4-ols, existing mainly as trans isomers. trans Orientation of perfluoroalkyl substituents in these compounds was determined by analysis of 19F-19F spin-spin coupling constants in the 19F NMR spectra. The molecular structure of trans-2-amino-5-fluoro-4,5-bis(trifluoromethyl)-4,5-dihydrooxazol-4-ol was studied by X-ray analysis. |
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