P 80 Polyfluoro-2,3-epoxyalkanes in reactions with thiourea and thiosemicarbazide [Text] / L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, V. I. Saloutin, G. G. Aleksandrov, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2000. - Vol. 36, № 6. - P887-899. - Bibliogr. : p. 899 (17 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): POLYFLUORO-2,3-EPOXYALKANES -- THIOUREA -- THIOSEMICARBAZIDE Аннотация: Reactions of polyfluoro-2,3-epoxyalkanes with thiourea and thiosemicarbazide afforded 2-amino-4-hydroxy-4,5-di(polyfluoroalkyl)-5-fluoro-1,3-thiazolines and 2-hydrazino-4-hydroxy-4,5-di(polyfluoroalkyl)-5-fluoro-1,3-thiazolines respectively. Unsymmetrical oxiranes furnish mixtures of regioisomeric heterocyclic compounds, and the epoxy cycle is predominantly cleaved from the side of bulkier fluoroalkyl group. The reactions of E-oxiranes are stereospecific and provide 1,3-thiazolines in the E-form. The structure of compounds obtained was confirmed by IR, 19F, 1H, and 13C NMR spectroscopy, by mass spectra and chemical transformations. E-isomers of 2-amino-4-hydroxy-4,5-bis(trifluoromethyl)-5-fluoro-1,3-thiazoline and 2-amino-5-heptafluoropropyl-4-hydroxy-4-trifluoromethyl-5-fluoro-1,3-thiazoline were subjected to X-ray diffraction analysis. |