S 98 Synthesis of fluorine containing glycolurils and oxazolines from oxides of internal perfluoroolefins [Text] / L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, P. A. Slepukhin, M. I. Kodess, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2009. - Vol. 130, № 10. - P853-860 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): OXIDES OF INTERNAL PERFLUOROOLEFINS -- 1,5-bIS(PERFLUOROALKYL)TETRAAZABICYCLO[3.3.0]OCTANE-3,7-D Аннотация: The reaction of oxides of internal perfluoroolefins 1–3 with urea gave two kinds of novel fluorine containing N-heterocyclic compounds depending on the solvent nature: 1,5-bis(perfluoroalkyl)tetraazabicyclo[3.3.0]octane-3,7-diones 4a–c and 2-amino-5-fluoro-4,5-bis(perfluoroalkyl)-4,5-dihydrooxazol-4-ols 7a–d. Use of polar dimethylsulfoxide, N,N-dimethylacetamide and acetonitrile afforded glycolurils 4a–c in moderate yields. In dioxane, unexpected cyclization occurred resulting in oxazolines 7a–d in high yields. A similar reaction of oxiranes 2, 3 with urea in aqueous dioxane gave mixtures of 4,5-dihydroxy-4,5-bis(perfluoroalkyl)imidazolidine-2-ones 9b, c, glycolurils 4b, c and oxazolines 7b–d. The molecular structure of trans-isomers of oxazoline 7b and imidazolidine 9b has been established by X-ray crystallography?? \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2009, V. 130, P. 853.pdf |