Abstract
3,3"-Bi(2-R-5,5-dimethyl-4-oxopyrrolinylidene) 1,1"-dioxides (R = CF3, Me, Ph, and But), which represent cyclic nitrons linked by the conjugated C=C bond, were shown to be strong electron-acceptors. The mechanism of their electrochemical reduction is the EE-type process including the consecutive formation of radical anions and dianions, which are stable under standard conditions. The radical anions of dinitrons, which are stable at 298 K and whose nitron group is not a part of the aromatic π-system and is not conjugated with it, were obtained for the first time and characterized by ESR spectroscopy in combination with quantum-chemical calculations.
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Shundrin, L.A., Reznikov, V.A., Irtegova, I.G. et al. Radical anions and dianions of 3,3"-bi(2-R-5,5-dimethyl-4-oxopyrrolinylidene) 1,1"-dioxides. Russian Chemical Bulletin 52, 939–943 (2003). https://doi.org/10.1023/A:1024460611872
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DOI: https://doi.org/10.1023/A:1024460611872