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

S. I. Zhivetyeva, I. A. Zayakin, I. Yu Bagryanskaya, E. V. Zaytseva, E. G. Bagryanskaya, E. V. Tretyakov

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

1 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)3924-3930
Число страниц7
ЖурналTetrahedron
Том74
Номер выпуска28
DOI
СостояниеОпубликовано - 12 июл 2018

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