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Investigation of keto-enol equilibrium of 3-alkylacetylacetones by the method of nuclear magnetic resonance

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    After alkylation of sodium acetylacetone with alkyliodides, individual 3-alkylacetylacetones were isolated from the reaction mixture and characterized. Our previous literature data pertained to substances containing an admixture of products of O-alkylation,

  2. 2.

    The NMR method was to determine the content of enol forms in the 3-alkylacetylacetones.

  3. 3.

    Alkylacetylacetones with unbranched substituents, according to the NMR data, contain cis-enol forms at equilibrium with the ketone, which agrees with the chemical data. Substances with branched substituents (3-iso-propylacetylacetone and 3-sec-butylacetylacetone) are almost pure ketones. The low enolization of these substances does not permit an assignment of the enol from to the cis-or trans-series by the NMR method.

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Literature cited

  1. S. T. Ioffe, E. M. Popov, K. V. Vatsuro, E. K. Tulikova, and M. I. Kabachnik, Tetrahedron,18, 923 (1962).

    Google Scholar 

  2. H. Henecka, Ber.,81, 179, 192 (1948).

    Google Scholar 

  3. S. J. Rhoads, R. W. Hasbrouck, C. Pryde, and R. W. Holder, Tetrahedron Letters,1963, No. 10, 669.

    Google Scholar 

  4. H. Jarrett, M. Sadler, and J. Shoolery, J. Chem. Phys.,21, 2092 (1953).

    Google Scholar 

  5. B. Bhar, Arkiv für Kemi,10, 223 (1956).

    Google Scholar 

  6. L. Reeves, Can. J. Chem.35, 1351 (1957).

    Google Scholar 

  7. L. Reeves and W. Schneider, Can. J. Chem.,36, 793 (1958).

    Google Scholar 

  8. F. Jose and B. Calleja. Compt rend,249, 1102 (1959).

    Google Scholar 

  9. J. R. Burdett and M. T. Rogers, J. Amer. Chem. Soc.,86, 2105 (1964).

    Google Scholar 

  10. L. Eberson and S. Forsen, J. Phys. Chem.,64, 767 (1960).

    Google Scholar 

  11. Ichiro Yamaguchi, Bull. Chem. Soc. Japan,34, 353 (1961).

    Google Scholar 

  12. K. Meyer, Ber.,45, 2846 (1912).

    Google Scholar 

  13. K. Auwers, Liebigs Ann. Chem.,426, 161 (1922).

    Google Scholar 

  14. M. Julia, Ann. Chimi, (12),5, 595 (1950).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences, USSR

    Yu. N. Molin, S. T. Ioffe, E. E. Zaev, E. K. Solov'eva, E. E. Kugucheva, V. V. Voevodskii & M. I. Kabachnik

  2. Institute of Chemical Kinetics and Combustion, Siberian Division, Academy of Sciences, USSR

    Yu. N. Molin, S. T. Ioffe, E. E. Zaev, E. K. Solov'eva, E. E. Kugucheva, V. V. Voevodskii & M. I. Kabachnik

Authors
  1. Yu. N. Molin
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  2. S. T. Ioffe
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  3. E. E. Zaev
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  4. E. K. Solov'eva
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  5. E. E. Kugucheva
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  6. V. V. Voevodskii
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  7. M. I. Kabachnik
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1556–1564, September, 1965

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Molin, Y.N., Ioffe, S.T., Zaev, E.E. et al. Investigation of keto-enol equilibrium of 3-alkylacetylacetones by the method of nuclear magnetic resonance. Russ Chem Bull 14, 1523–1530 (1965). https://doi.org/10.1007/BF01083792

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  • DOI: https://doi.org/10.1007/BF01083792

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