Synthesis of fluorine containing glycolurils and oxazolines from oxides of internal perfluoroolefins / Saloutina Lyudmila V.,Zapevalov Aleksandr Ya.,Saloutin Victor I.,Slepukhin Pavel A.,Kodess Mikhail I.,Chupakhin Oleg N. // JOURNAL OF FLUORINE CHEMISTRY. - 2009. - V. 130, l. 10. - P. 853-860.

ISSN/EISSN:

0022-1139 / нет данных

Type:

Article

Abstract:

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. (C) 2009 Elsevier B.V. All rights reserved.

Author keywords:

Oxides of internal perfluoroolefins; Urea; 1,5-Bis(perfluoroalkyl)tetraazabicyclo{[}3.3.0]octane-3,7-diones; 2-Amino-5-fluoro-4,5-bis(perfluoroalkyl)-4,5-dihydrooxazol-4-ols; 4,5-Dihydroxy-4,5-bis(per

DOI:

10.1016/j.jfluchem.2009.06.016

Web of Science ID:

ISI:000271345400001

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
Author-Email	fc403@ios.uran.ru
Funding-Acknowledgement	Russian Federation {[}3758.2008.3]
Funding-Text	The research has been financially supported by the State Program for supporting leading scientific schools of Russian Federation (grant no. 3758.2008.3).
Number-of-Cited-References	19
Usage-Count-Since-2013	2
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	513TD