S-N(H) Approach in the Synthesis of Nitronyl Nitroxides / Chupakhin Oleg N.,Utepova Irina A.,Varaksin Mikhail V.,Tretyakov Evgeny V.,Romanenko Galina V.,Stass Dmitry V.,Ovcharenko Victor I. // JOURNAL OF ORGANIC CHEMISTRY. - 2009. - V. 74, l. 7. - P. 2870-2872.

ISSN/EISSN:

0022-3263 / нет данных

Type:

Article

Abstract:

We show that the S-N(H) approach opens up new possibilities in the synthesis of hetaryl-substituted nitronyl nitroxides. The reaction of 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl lithium salt with pyridine-, pyrimidine-, pyrazine-, isoquinoline-, phthalazine-, quinoxaline-, and 1,2,4-triazine-N-oxides readily gives rise to the corresponding paramagnetic hetarenes. The reaction of this salt with quinoxaline-1,4-dioxide enabled the synthesis of the first nitronyl nitroxide biradical with two spin-labeled fragments in the vicinal positions of the heteroaromatic cycle; the persistent biradicals of this type were not known earlier. The characterizations of all persistent radicals obtained by S-N(H) synthetic strategy include X-ray crystal structures, EPR investigation, and static magnetic susceptibility measurements.

Author keywords:

MOLECULAR MAGNETIC-MATERIALS; STABLE FREE RADICALS; SYSTEMS

DOI:

10.1021/jo900085s

Web of Science ID:

ISI:000264627400035

Соавторы в МНС:

Другие поля

Поле	Значение
Month	APR 3
Publisher	AMER CHEMICAL SOC
Address	1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Language	English
Keywords-Plus	MOLECULAR MAGNETIC-MATERIALS; STABLE FREE RADICALS; SYSTEMS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	chupakhin@ios.uran.ru tev@tomo.nsc.ru
ResearcherID-Numbers	Tretyakov, Evgeny/A-7163-2014 Varaksin, Mikhail/J-5007-2015
ORCID-Numbers	Tretyakov, Evgeny/0000-0003-1540-7033 Varaksin, Mikhail/0000-0002-7997-3686 Romanenko, Galina/0000-0001-8852-2759 Stass, Dmitri/0000-0003-3510-5219
Funding-Acknowledgement	RFBR {[}06-03-32157, 08-03-00025, 08-03-00038]; Russian Federation {[}NSh-1213.2008.3]
Funding-Text	The financial support by RFBR (grants 06-03-32157, 08-03-00025, 08-03-00038), RAS, SB RAS, the Program for State Support of Leading Scientific Schools of the Russian Federation (Grant NSh-1213.2008.3), and the Bruker firm is gratefully acknowledged.
Number-of-Cited-References	21
Usage-Count-Since-2013	21
Journal-ISO	J. Org. Chem.
Doc-Delivery-Number	425HK