Summary
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1.
The methyl ester of phenylnitromethane reacts by the 1,3-dipolar addition scheme with compounds, containing an activated double bond, with the formation of 5-substituted 3-phenyl-N-methoxyisoxazolidine derivatives.
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2.
The reaction of the N-methoxyisoxazolidines with LiAlH4 leads to their conversion to the corresponding isoxazoline derivatives.
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3.
The methyl ester of phenylnitromethane enters into the 1,3-dipolar addition reaction across the C=N bond in oximes. As the result of spontaneous aromatization, the formed adduct is converted to the oxadiazole derivative.
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Literature cited
R. Huisgen, Angew. Chemie,75, 604 (1963).
V. A. Tartakovskii, I. E. Chlenov, S. S. Smagin, and S. S. Novikov, Izv. AN SSSR, Ser. Khim.,1964, 583.
G. Stagno d'Alcontres and P. Grünanger, Gazz. Chim. Ital.,80, 744 (1950).
F. Arndt and J. D. Rose, J. Chem. Soc.,1935, 6.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 552–554, March, 1965
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Tartakovskii, V.A., Smagin, S.S., Chlenov, I.E. et al. Methyl ester of phenylnitromethane in the 1,3-dipolar cycloaddition reaction. Russ Chem Bull 14, 534–536 (1965). https://doi.org/10.1007/BF00846623
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DOI: https://doi.org/10.1007/BF00846623