Interaction of a lithiated nitronyl nitroxide with polyfluorinated 1,4-naphthoquinones

Interaction of a lithiated nitronyl nitroxide with polyfluorinated 1,4-naphthoquinones Научная публикация

Журнал

Tetrahedron
ISSN: 0040-4020

Вых. Данные

Год: 2018, Том: 74, Номер: 28, 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	(Данные Web of science) NN Vorozhtsov Inst Organ Chem, 9 Ac Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia

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 degrees 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-2yl)-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. (C) 2018 Elsevier Ltd. All rights reserved.

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. N28. P.3924-3930. DOI: 10.1016/j.tet.2018.05.075 WOS Scopus РИНЦ

Опубликована в печати:

1 июл. 2018 г.

Web of science	WOS:000436914900014
Scopus	2-s2.0-85048315684
РИНЦ	35779120
OpenAlex	W2805183730