Conclusions
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1.
Reduction of nitroacetonitrile and 2-cyano-2-nitropropane proceeds through attack at the nitrogroup N-O bond.
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2.
The details of the structure of the anion formed through C-N bond rupture will determine whether nitroalkane reduction, will proceed through the C-N or N-O bonds.
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Literature cited
V. A. Petrosyan, V. V. Paramonov, V. I. Slovetskii, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 1719 (1976).
V. A. Petrosyan, V. V. Paramonov, V. I. Slovetskii, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 2252 (1977).
V. A. Pal'm, Usp. Khim.,30, 1069 (1961).
V. I. Slovetskii, S. A. Shevelev, A. A. Fainzil'berg, and S. S. Novikov, Zh. Vses. Khim. Obshch.,6, 599, 707 (1961).
W. Steinkopf and L. Bohrmann, Ber.,41, 1044 (1908).
W. Steinkopf and A. Supan, Ber.,44, 2895 (1911).
N. Kornblum, R. J. Clutter, and W. J. Jones, J. Am. Chem. Soc.,78, 4003 (1956).
S. G. Mairanovskii, V. A. Petrosyan, V. I. Slovetskii, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 2390 (1969).
F. Petru, Collect. Czech. Commun.,12, 620 (1947).
M. Masui, H. Sayo, and K. Kishi, Chem. Pharm. Bull.,12, 1397 (1964).
V. T. Novikov, Dissertation, Moscow, 1975, p. 104.
W. Ried and E. Kohler, Liebigs Ann. Chem.,598, 145, 154 (1956).
M. Masui and H. Sayo, J. Chem. Soc., 1733 (1962).
J. Armand, Bull. Soc. Chim. France, 543 (1966).
M. Masui and C. Yijima, J. Chem. Soc., 1101 (1963).
G. Foier, Chemistry of the Nitro and Nitroso Groups [Russian translation], Mir, (1972), p. 279.
V. A. Petrosyan, V. I. Slovetskii, S. G. Mairanovskii, and A. A. Fainzil'berg, Elektrokhimiya,6, 1595 (1970).
V. A. Petrosyan, V. M. Khutoretskii, L. V. Okhlobystina, andV. I. Slovetskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2023 (1973).
R. G. Pierson and R. L. Dillon, J. Am. Chem. Soc.,75, 2439 (1953).
V. A. Petrosyan, V. I. Slovetskii, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 2027 (1973).
V. A. Petrosyan, S. G. Mairanovskii, L. V. Okhlobystina, V. I. Slovetskii, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim., 1690 (1971).
V. V. Paramonov, V. A. Petrosyan, and V. I. Slovetskii, Izv. Akad. Nauk SSSR, Ser. Khim., 567 (1977).
A. G. Bazanov, M. U. Chistyakova, M. F. Kozlova, I. V. Tselinskii, and B. V. Gidaspov, Reakts. Sposobn. Org. Soedin.,10, 807 (1973).
J. P. Lorand, J. Urban, J. Overs, and Q. A. Ahmed, J. Org. Chem.,34, 4176 (1969).
I. M. Filatova, K. K. Babievskii, V. T. Novikov, I. A. Avrutskaya, V. M. Belikov, and M. Ya. Fioshin, Polarography News 1975. Abstracts of Reports, Sixth All-Union Conference on Polarography, Riga (1975), p. 144.
D. J. Cram, Fundamentals of Carbanion Chemistry, Academic Press (1965).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 793–799, April, 1978.
The authors would like to thank A. V. Sultanov for his aid in synthesizing the compounds used in this work.
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Petrosyan, V.A., Paramonov, V.V., Slovetskii, V.I. et al. Polarographic study of aliphatic nitro compounds 11. Reduction of nitroalkanes with an electronegative substituent in the α position. Russ Chem Bull 27, 684–689 (1978). https://doi.org/10.1007/BF00925284
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DOI: https://doi.org/10.1007/BF00925284