Condensation of fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones with methylamine / Shchegol'kov E. V.,Burgart Ya. V.,Slepukhin P. A.,Kazheva O. N.,Shilov C. V.,D'yachenko O. A.,Saloutin V. I. // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2007. - V. 43, l. 12. - P. 1788-1796.

ISSN/EISSN:

1070-4280 / нет данных

Type:

Article

Abstract:

Fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones react with methylamine in different ways, depending on the substrate structure. Arylhydrazones having a short fluoroalkyl substituent (R-F = CF3, HCF2CF2) react at the carbonyl group adjacent to the nonfluorinated substituent to give 3-alkyl(aryl)-2-aryldiazenyl-3-methylamino-1-polyfluoroalkylprop-2-en-1- ones. Arylhydrazones with a long-chain fluoroalkyl group (RF = C3F7 and longer) and a bulky nonfluorinated group take up methylamine molecule at the carbonyl group linked to the fluorinated substituent, and the subsequent haloform reaction yields N-methyl-2-arylhydrazono-3-oxobutanamides. Both types of products are formed in reactions of methylamine with 1,2,3-triketone 2-arylhydrazones having a long fluoroalkyl group and methyl group at the other carbonyl group. L Template condensation of fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones with methylamine over Ni(II) template gives bis{[}3-alkyl(aryl)-1-polyfluoroalkyl-3-methylamino-2-aryldiazenylprop-2 -en-1-onato-N,N']nickel(II), regardless of the size of the fluoroalkyl substituent. The same complexes and their copper analogs can be obtained by treatment of 3-alkyl(aryl)-2-aryldiazenyl-3-methylamino-1-polyfluoroalkylprop-2-en-1- ones with the corresponding metal salts.

Author keywords:

нет данных

DOI:

10.1134/S1070428007120081

Web of Science ID:

ISI:000252852300008

Соавторы в МНС:

Другие поля

Поле	Значение
Month	DEC
Publisher	MAIK NAUKA/INTERPERIODICA/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	saloutin@ios.uran.ru
ResearcherID-Numbers	Shchegol'kov, Evgenii/H-6790-2015 Burgart, Yanina/T-8025-2017
ORCID-Numbers	Shchegol'kov, Evgenii/0000-0001-6611-2855 Burgart, Yanina/0000-0001-6061-2410
Number-of-Cited-References	15
Usage-Count-Since-2013	5
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	258EX