Synthesis of fluorine containing N-heterocycles using oxides of terminal perfluoroolefins and urea / Saloutina Lyudmila V.,Zapevalov Aleksandr Ya.,Kodess Mikhail I.,Slepukhin Pavel A.,Saloutin Victor I.,Chupakhin Oleg N. // JOURNAL OF FLUORINE CHEMISTRY. - 2012. - V. 139, l. . - P. 16-22.

ISSN/EISSN:

0022-1139 / нет данных

Type:

Article

Abstract:

The reaction of octafluoro-1,2-epoxybutane (1) with urea in Me2SO, aqueous Me2SO, aqueous dioxane, aqueous acetonitrile and of hexadecafluoro-1,2-epoxyoctane (2) with urea in aqueous Me2SO gave perfluoroalkylhydantoins - 5-hydroxy-5-pentafluoroethylimidazolidine-2,4-dione (4a) (yield 40-42\%) and 5-hydroxy-5-tridecafluorohexylimidazolidine-2,4-dione (4b) (yield 54\%), respectively. Use of dioxane and acetonitrile in the reaction of oxiranes 1, 2 with urea led to unexpected heterocyclic products - perfluoroalkyloxazoles 7a, b (yield 11-82\%). Perfluoroalkyl containing allantoin - 5-tridecafluorohexyl-5-ureidoimidazolidine-2,4-dione (3b) (yield 19\%) and polyfluoroalkyl containing urea-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-hydroxyheptyl)urea (6b) (yield 46\%) have been first obtained by the reaction of oxirane 2 with urea in Me2SO and aqueous Me2SO, respectively. The molecular and crystal structure of hydantoin 4a has been studied by X-ray crystallography. (C) 2012 Elsevier B.V. All rights reserved.

Author keywords:

Perfluoro-1,2-epoxyalkanes; Urea; Perfluoroalkyl containing hydantoins; Perfluoroalkyl containing oxazoles; Perfluoroalkyl containing allantoins; Polyfluoroalkylurea TRIFLUOROPYRUVIC ACID HYDRATE

DOI:

10.1016/j.jfluchem.2012.03.017

Web of Science ID:

ISI:000305204100003

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
Keywords-Plus	TRIFLUOROPYRUVIC ACID HYDRATE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
Author-Email	fc403@ios.uran.ru
Funding-Acknowledgement	Russian Federation {[}5505.2012.3]; Urals Branch of the Russian Academy of Sciences {[}12-P-3-1030, 12-T-3-1025]
Funding-Text	The research has been financially supported by the State Program for supporting leading Scientific Schools of Russian Federation (Grant no. 5505.2012.3) and Projects of Urals Branch of the Russian Academy of Sciences (12-P-3-1030 and 12-T-3-1025).
Number-of-Cited-References	25
Usage-Count-Since-2013	3
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	957YX