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- Title
Reactions of internal perfluoroolefin oxides with urea.
- Authors
Saloutina, L. V.; Zapevalov, A. Ya.; Saloutin, V. I.; Kodess, M. I.; Slepukhin, P. A.
- 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)tetraazabicyclo[3.3.0]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.
- Subjects
OXIDES; HETEROCYCLIC compounds; DIMETHYL sulfoxide; ACETONITRILE; DIOXANE
- Publication
Russian Journal of Organic Chemistry, 2009, Vol 45, Issue 6, p865
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428009060116