Conclusions
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1.
Depending on the ratios of the reactants, the electronic transfer from the dipotassium salt of the dianion of cyclooctatetraene to m-dinitrobenzene in THF solution leads either to the K-salts of the anion-radical or to the dianion of the dinitro compound.
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2.
The K-salt of the dianion of m-dinitrobenzene reacts with acetone in the presence of oxidizing agents, giving the K-salt of 2, 4-dinitrocyclohexadienylacetone (Yanovskii σ-complex). The anion-radical of m-dinitrobenzene is incapable of such reaction.
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3.
The reaction of acetone with m-dinitrobenzene in alkaline medium (Yanovskii reaction) can include the steps: formation of the dianion of the dinitro compound, reaction of the latter with acetone, and the one-electron oxidation of the addition product, leading to the formation of the Yanovskii σ-complex.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1083–1088, May, 1972.
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Gol'teuzen, É.É., Todres, Z.V., Kaminskii, A.Y. et al. Role of electronic transfers in mechanism for the reaction of acetone with aromatic dinitro compounds. Russ Chem Bull 21, 1038–1042 (1972). https://doi.org/10.1007/BF00853764
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DOI: https://doi.org/10.1007/BF00853764