2,3-Epoxyperfluoro-2-methylpentane in reactions with urea and thiourea / Filyakova T. I.,Saloutina L. V.,Zapevalov A. Ya,Slepukhin P. A.,Kodess M. I.,Saloutin V. I. // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2011. - V. 47, l. 5. - P. 650-658.

ISSN/EISSN:

1070-4280 / 1608-3393

Type:

Article

Abstract:

2,3-Epoxyperfluoro-2-methylpentane reacts with thiourea in protic (methanol, 2-propanol) and aprotic (dioxane) solvents, and also with urea in acetonitrile affording unexpected products: 1-(2,2,3,3,3-pentafluoropropionyl)-2-(2,2,2-trifluoro-1-trifluoro-methyl ethyl)isothiourea, and 1-(2,2,3,3,3-pentafluoropropionyl)-3-(2,2,2-trifluoro-1-trifluoro-methyl ethyl)urea respectively that result from the rearrangement of the intermediately formed ketone in the process of the intramolecular ``haloform{''} cleavage. At the same time in dioxane the 2,3-epoxyperfluoro-2-methylpentane reacts with urea with the formation of a heterocyclic compound, 2-amino-4-pentafluoroethyl-5,5-bis(trifluoromethyl)-4,5-dihydrooxazol-4- ol. From 1-(2,2,3,3,3-pentafluoropropionyl)-2-(2,2,2-trifluoro-1-trifluoromethyle thyl)isothiourea and Cu(OAc)(2) a stable fluorine-containing chelate complex was obtained.

Author keywords:

PERFLUORINATED ALPHA-OXIDES; AMMONIUM

DOI:

10.1134/S107042801105022

Web of Science ID:

ISI:000291487300002

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY
Publisher	MAIK NAUKA/INTERPERIODICA/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
EISSN	1608-3393
Keywords-Plus	PERFLUORINATED ALPHA-OXIDES; AMMONIUM
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	fc403@ios.uran.ru
Funding-Acknowledgement	President of the Russian Federation {[}NSh-65261.2010.3]; Ural Division of the Russian Academy of Sciences {[}09-P-3-1013, 09-C-3-1002, 09-M-23-2006, 09-P-3-2001]
Funding-Text	The study was carried out under a financial support of the Council on grants of the President of the Russian Federation (the program of support of leading scientific schools, grant NSh-65261.2010.3) and of projects of Ural Division of the Russian Academy of Sciences 09-P-3-1013, 09-C-3-1002, 09-M-23-2006, 09-P-3-2001.
Number-of-Cited-References	24
Usage-Count-Since-2013	3
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	775TW