Conclusions
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1.
The reaction of fluorine with the potassium salt of dinitroacetonitrile in the presence of potassium fluoride leads not only to replacement of the cation of the salt by the fluorine atom, but also to the addition of fluorine to the multiple bonds of the nitrile group. The reaction of fluorine with the sodium salt of dinitroacetonitrile in the presence of calcium fluoride gives fluorodinitroacetonitrile.
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2.
The electrophilic character of the nitrile grouping in fluorodinitroacetonitrile was shown on the examples of the reactions with ammonia, methanol, and difluoronitroethanol. The previously unknown hydrochloride of fluorodinitroacetamidine, and the methyl and difluoronitroethyl esters of iminofluorodinitroacetic acid, were obtained.
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Literature cited
L. T. Eremenko, F. Ya. Natsibullin, and I. P. Borovinskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 429 (1968).
A. V. Fokin, V. S. Galakhov, and V. P. Radchenko, Zh. Obshch. Khim.,39, 1605 (1969).
A. V. Fokin, V. S. Galakhov, and V. P. Radchenko, ibid.,39, 1345 (1969).
C. O. Parker, Tetrahedron,17, 109 (1962).
J. K. Ruff, J. Org. Chem.,32, 1675 (1967).
R. A. Wiesboeck and J. K. Ruff, ibid.,33, 1257 (1968).
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 456–458, February, 1974.
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Fokin, A.V., Galakhov, V.S., Uzun, A.T. et al. Reaction of fluorine with alkali metal salts of dinitroacetonitrile in presence of potassium or calcium fluorides. Russ Chem Bull 23, 425–427 (1974). https://doi.org/10.1007/BF00924706
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DOI: https://doi.org/10.1007/BF00924706