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Interaction of a Lithiated Nitronyl Nitroxide with Polyfluorinated 1,4-Naphthoquinones Научная публикация

Общая информация Язык: Английский, Жанр: Статья (Full article),
Статус опубликования: Опубликована, Оригинальность: Оригинальная
Журнал Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416
Вых. Данные Год: 2018, Том: 74, Страницы: 3924-3930 Страниц : 7 DOI: 10.1016/j.tet.2018.05.075
Ключевые слова Nitronyl nitroxides Iminonitroxides 1,4-Naphthoquinones Organic diradicals X-ray diffraction study ESR spectra
Авторы Zhivetyeva S.I. 1 , Zayakin I.A. 1,2 , Bagryanskaya I.Yu. 1,2 , Zaytseva E.V. 1 , Bagryanskaya E.G. 1 , Tretyakov E.V. 1,2
Организации
1 N. N. Vorozhtsov Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, Novosibirsk, 630090, Russia
2 Novosibirsk State University, 2 Pirogova Str, Novosibirsk, 630090, Russia

Информация о финансировании (1)

1 Российский научный фонд 17-73-10238 (АААА-А17-117073110021-4)

Реферат: A 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl lithium derivative was found to react with 2-methoxypentafluoro-1,4-naphthoquinone to form a product of addition at the carbonyl function: radical 2-(3,5,6,7,8-pentafluoro-1-hydroxy-2-methoxy-4-oxo-1,4-dihydronaphthalen-1-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl. The yield of the addition product increased with temperature and reached 84% at 0 C. The reaction of the lithium derivative with hexafluoro-1,4-naphthoquinone gave rise to a product of addition at both carbonyl groups, namely, nitronyl nitroxide diradical 2,3,5,6,7,8-hexafluoro-1,4-bis(4,4,5,5-tetramethyl-3-oxide-1-oxyl-4,5-dihydro-1H-imidazole-2-yl)-1,4-dihydronaphthalene-1,4-diol in a 16% yield. The structures of both mono- and diradical were solved by X-ray diffraction analysis, which revealed formation of an intramolecular H-bond between the OH group and nitroxide oxygen. According to electron paramagnetic resonance (EPR) spectroscopy, the obtained mono- and dinitroxide are prone to spontaneous deoxygenation in a toluene solution to give corresponding iminonitroxides. In water, they are much more stable.
Библиографическая ссылка: Zhivetyeva S.I. , Zayakin I.A. , Bagryanskaya I.Y. , Zaytseva E.V. , Bagryanskaya E.G. , Tretyakov E.V.
Interaction of a Lithiated Nitronyl Nitroxide with Polyfluorinated 1,4-Naphthoquinones
Tetrahedron. 2018. V.74. P.3924-3930. DOI: 10.1016/j.tet.2018.05.075 WOS Scopus РИНЦ
Даты:
Поступила в редакцию: 4 мая 2018 г.
Принята к публикации: 26 мая 2018 г.
Опубликована online: 28 мая 2018 г.
Опубликована в печати: 1 июл. 2018 г.
Идентификаторы:
Web of science WOS:000436914900014
Scopus 2-s2.0-85048315684
РИНЦ 35779120
Chemical Abstracts 2018:1076113
Chemical Abstracts (print) 169:102614
Альметрики: