Abstract
The reaction ofZ-2-furaldoxime with oxirane afforded theN-alkylation product,viz., α-2-furyl-N-(2-hydroxyethyl)nitron, in good yield.E-Benzaldoxime gave predominantly theO-alkylation product, while itsZ isomer was converted into a mixture with theN-alkylation product slightly predominating.
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References
G. B. Bachman and T. Hokama,J. Am. Chem. Soc., 1959,81, 4223.
W. Kliegel,Liebigs Ann. Chem., 1970,733, 192.
Svoistva organicheskikh soedinenii. Spravochnik [Properties of Organic Compounds. Handbook], Ed. A. A. Potekhin, Khimiya, Leningrad, 1984 (in Russian).
E. Buchler,J. Org. Chem., 1967,32, 261.
R. Grigg and J. Markandu,Tetrahedron Lett., 1989,30, 5489.
W. Kliegel and H. Becker,Chem. Ber., 1977,110, 2067.
S. Sivasubramanian, P. Mohan, M. Thirumalaikumar, and S. Muthusubramanian,J. Chem. Soc., Perkin Trans. 1, 1994. 3353.
J. Bjorgo, D. R. Boyd, and D. C. Neill,J. Chem. Soc., Chem. Commun., 1974,12, 478.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1403–1404, July, 1999.
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Bakunova, S.M., Grigor'ev, I.A. & Volodarsky, L.B. Influence ofE/Z isomerism of aldoximes on the direction of their alkylation with oxirane. Russ Chem Bull 48, 1389–1391 (1999). https://doi.org/10.1007/BF02495314
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DOI: https://doi.org/10.1007/BF02495314