Abstract
We have studied the reaction of nitrile oxides with nitrogen tetroxide. It was shown that the reaction is selective: acetonitrile oxide yields ethylnitrolic acid, α-oximinophenylacetonitrile oxide gives a mixture of isomers of phenylnitrofuroxan, and aromatic nitrile oxides give aryltrinitromethanes.
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Literature cited
C. Grundmann and P. Grunanger, The Nitrile Oxides, Springer Verlag, Berlin-Heidelberg-New York (1971).
P. Gray and A. D. Joffe, Chem. Rev.,55, 1069 (1955).
T. Caronna, A. Qiulico, and F. Minisci, Tetrahedron Lett., 3633 (1970).
T. Mukaiyama and T. Hoshino, J. Am. Chem. Soc.,82, 5339 (1960).
A. I. Timov and V. V. Smirnov, Dokl. Akad. Nauk SSSR,83, 243 (1952).
A. A. Potekhina (ed.), Properties of Organic Compounds (a Handbook) [in Russian], Khimiya, Leningrad (1984).
A. Qiulico, Isoxazoles and Related Compounds. The Chemistry of Heterocyclic Compounds, A. Weissberger (ed.), Vol. 17, p. 21.
L. I. Khmel'nitskii, S. S. Novikov, and O. V. Lebedev, Izv. Akad. Nauk SSSR, Otd. Khim., 2019 (1960).
E. Zinner and H. Guntner, Angew. Chem.,76, 440 (1964).
V. Meyer, J. Liebigs Ann. Chem.,175, 88 (1875).
G. Ponzio, Gazz. Chim. Ital.,66, 123 (1936).
N. N. Makhova, I. V. Ovchinnikov, B. N. Khasapov, and L. I. Khmel'nitskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 646 (1982).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1620–1622, July, 1990.
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Rakitin, O.A., Ogurtsov, V.A., Godovikova, T.I. et al. Reactions of nitrile oxides with nitrogen oxides. 1. Reactions with nitrogen tetroxide. Russ Chem Bull 39, 1469–1471 (1990). https://doi.org/10.1007/BF00957862
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DOI: https://doi.org/10.1007/BF00957862