Conclusions
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1.
From a comparison of the constants of the nitrogen splitting, it has been shown that in the radical anion of nitrocyclopropane delocalization of the unpaired electron over the three-membered ring comparable with that in nitroolefins is observed. The EPR spectrum with HFS for the protons of the ring has been obtained in dimethylformamide.
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2.
In the radical anions of tertiary nitroalkanes a decrease in the nitrogen splitting with the introduction of electronegative substituents has been observed.
Literature cited
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L. H. Piette, P. Ludwig, and R. N. Adams, J. Amer. Chem. Soc.84, 4212 (1962).
M. Karplus and G. K. Fraenkel, J. Chem. Phys.35, 1312 (1961).
P. G. Bay, U. S.Patent 3,100,805; Chem.Abstrs.60, P4216d (1963).
H. B. Hass and H. Shechter, J. Amer. Chem. Soc.75, 1382 (1953).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1105–1107, June, 1966.
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Prokof'ev, A.I., Chibrikin, V.M., Yuzhakova, O.A. et al. EPR spectra of radical anions obtained in the electrochemical reduction of nitrocyclopropane, nitroalkanes, and nitroalkylenes. Russ Chem Bull 15, 1060–1062 (1966). https://doi.org/10.1007/BF00846074
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DOI: https://doi.org/10.1007/BF00846074