Exploration of SNF-Approach toward Functionalized Nitronyl Nitroxides

Abstract

A 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl lithium derivative was found to react with perfluoroaromatic compounds with formation of products of fluoro-atom substitution, namely fluorinated aryl(hetaryl)-substituted nitronyl nitroxides. The yields of the fluorinated nitroxides were acceptable in cases of reactions with functionalized perfluorobenzene and perfluoropyridine (25–60%), but was low in case of reaction with perfluorobiphenyl (~ 5%). Molecular and crystal structures of the obtained nitronyl nitroxides were solved by monocrystal Xray diffraction analysis, and the nature of the radical was ascertained by EPR.