Interaction of a Lithiated Nitronyl Nitroxide with Polyfluorinated 1,4-Naphthoquinones Научная публикация
Журнал |
Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416 |
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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 |
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Организации |
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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
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 БД:
Web of science | WOS:000436914900014 |
Scopus | 2-s2.0-85048315684 |
РИНЦ | 35779120 |
Chemical Abstracts | 2018:1076113 |
Chemical Abstracts (print) | 169:102614 |
OpenAlex | W2805183730 |