Conclusions
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1.
The content of enol forms of chromatographically pureα-alkylacetoacetic esters and 3-alkylacet-ylacetones in various solvents was determined by the method of bromometric titration.
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2.
The introduction of branched substituents, as a result of steric hindrances, leads to a sharp decrease in the enolization, but not to the appearance of the trans-enol form, as we and other authors had earlier proposed.
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3.
The change in the content of the enol form in various solvents obeys the Meyer rule, which indicates cis-enolization of the compounds studied.
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Literature cited
H. Henecak, Ber.,81, 192 (1948).
D. N. Shigorin and A I. Skoldinov, ZhFKh,24, 955 (1950).
M. I. Kabachnik, S. T. Ioffe, E. M. Popov, and K. V. Vatsuro, ZhOKh,31, 2682 (1961).
S. J. Rhoads, R. W. Hasbrouck, and O. Pryde, Tetrahedron Letters, 669 (1963).
S. T. Ioffe, K. V. Vatsuro, E. E. Kugucheva, and M. I. Kabachnik, ZhOrKh,2, 381 (1966).
K. Meyer, Ber.,47, 826 (1914).
F. Korte and F. Wüsten, Tetrahedron,19, 1423 (1963).
P. Russel and J. Mentra, J. Amer. Chem. Soc.,77, 4245 (1955).
S. T. Yoffe, E. I. Fedin, P. V. Petrovskii, and M. I. Kabachnik, Tetrahedron Letters, 2661 (1966).
A. Ness and S. M. McElvain, J. Amer. Chem. Soc.,60, 2213 (1938).
R. R. Briese and S. M. McElvain, J. Amer. Chem. Soc.,55., 1697 (1933).
W. Dieckmann, Ber.,55, 2470 (1922).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2024–2027, September, 1968.
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Ioffe, S.T., Vatsuro, K.V. & Kabachnik, M.I. Enolization of α-alkylacetoacetic esters and 3-alkylacetylacetones in solutions. Russ Chem Bull 17, 1927–1930 (1968). https://doi.org/10.1007/BF00904985
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DOI: https://doi.org/10.1007/BF00904985