Abstract
The reaction of 2-acetyloxiranes with alkyl thiocyanates in the presence of Lewis acids (BF3, AlCl3) has given 2-alkylthio-5-acetyl-2-oxazolines (yields 40–60%). It has been shown that the reaction of trans-2-acetyl-3-methyloxirane and of trans-2-acetyl-3-methyloxirane and of trans-2-acetyl-2,3-dimethyloxirane with alkyl thiocyanates takes place stereospecifically and leads to cis-2-alkylthio-5-acetyl-2-oxazolines.
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O. N. Bubel', I. G. Tishchenko, and O. A. Grinkevich, Khim. Geterotsikl. Soedin., No. 4, 460 (1979).
U. Schollköpf, G. Fritz, J. Hoppe, R. Harms, K. Hantke, K. D. Scheunemann, E. Eilers, and E. Blume, Ann. Chem., No. 1, 183 (1976).
V. N. Yandovskii and T. I. Temnikova, Zh. Org. Khim.,4, 1758 (1968).
C. L. Van Antwerp, J. Chem. Educ.,50, 638 (1973).
P. Allen, J. Am. Chem. Soc.,57, 198 (1935).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 468–471, April, 1980.
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Bubel', O.N., Tishchenko, I.G., Grinkevich, O.A. et al. Synthesis of 2-alkylthio-5-acetyl-2-oxazolines. Chem Heterocycl Compd 16, 352–355 (1980). https://doi.org/10.1007/BF00552772
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DOI: https://doi.org/10.1007/BF00552772