Abstract
The 4-nitro derivative is formed in the nitration of 3,5-diphenylisoxazole (I) in acetic anhydride. Mononitration of isoxazole I in concentrated H2SO4 gave 3-phenyl-5-(p-nitrophenyl)isoxazole, while polynitration gave a mixture of dinitro derivatives, among which 3- (m-nitro-phenyl)-5-(p-nitrophenyl)isoxazole was identified. The structures of the isolated products were established by means of the spectra, by reaction-chromatography methods, and gasliquid chromatography, as well as by a comparison with genuine samples of the two mononitro and four dinitro derivatives of isoxazole I.
Similar content being viewed by others
Literature cited
S. D. Sokolov, T. N. Egorova, and N. S. Kuryatov, Khim. Geterotsikl. Soedin., 1329 (1973).
M. R. Langella and P. Vita Finzi, Chim. Ind. (Milano), 47, 996 (1965).
B. M. Lynch and L. Shiu, Canad. J. Chem., 43, 2117 (1965).
S. D. Sokolov and I. M. Yudintseva, Zh. Organ. Khim., 4, 2057 (1968).
C. Musante, Farm. Sci. Tec. (Pavia), 6, 32 (1951); Chem. Abstr., 45, 5879 (1951).
S. D. Sokolov, L. A. Kazitsyna, and L. K. Guseva, Zh. Organ. Khim., 2, 731 (1966).
T. A. Babushkina, G. K. Semin, S. D. Sokolov, and I. M. Yudintseva, Izv. Akad. Nauk SSSR, Ser. Khim., 2376 (1970).
G. E. Lewis, J. Org. Chem., 30, 2798 (1965).
G. P. Sharnin, I. E. Moisak, E. E. Gryazin, and I. F. Falyakhov, Zh. Organ. Khim., 3, 1836 (1967).
V. V. Zverev, G. P. Sharnin, and I. D. Morozova, Izv. Akad. Nauk SSSR, Ser. Khim., 404 (1968).
M. L. Scheinbaum, Chem. Commun., 1235 (1969).
F. Bell, J. Kenyon, and P. H. Robinson, J. Chem. Soc., 1239 (1926).
M. A. Paul, J. Amer. Chem. Soc., 80, 5332 (1958).
S. D. Sokolov, I. M. Yudintseva. P. V. Petrovskii, and V. G. Kalyuzhnaya. Zh. Organ. Khim., 7, 1979 (1971).
R. P. Barnes and L. B. Dodson, J. Amer. Chem. Soc., 67, 132 (1945).
A. H. Blatt, J. Amer. Chem. Soc., 71, 1861 (1949).
P. Klinke and H. Gibian, Chem. Ber., 94, 26 (1961).
J. Frank and K. Pospisilova, J. Chromatogr., 48, 207 (1970).
M. Arbasino and P. Grünanger, Ric. Sci., 34, (II-A), 561 (1964).
U. Türck and H. Behringer, Chem. Ber.. 98, 3020 (1965).
G. Bianchetti, D. Pocar, and P. Dalla Croce, Gazz. Chim. Ital., 93, 1714 (1963).
Author information
Authors and Affiliations
Additional information
See [1] for communication XXVII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 597–601, May, 1974.
Rights and permissions
About this article
Cite this article
Sokolov, S.D., Egorova, T.N. & Yudintseva, I.M. Research in the isoxazole series. Chem Heterocycl Compd 10, 516–520 (1974). https://doi.org/10.1007/BF00471316
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00471316