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Cycloketonization and linear polyketonization of α, ω-dicarboxylic acids

Communication 5. Synthesis of dispiro[5.2.5.3]heptadecan-16-one and some new data on cycloketonization mechanism

  • Organic and Biological Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Confirmation was obtained for the previously made conclusion regarding the effect of the 1,3-interactions of the CH3 groups with the H atoms of the backbone chain of a dicarboxylic acid molecule on the yields of the cycloketonization products. At the same time it was shown that an increase in the conformational strain of the ring does not lead to a decrease in the yield of a cyclic ketone with a sevenmembered ring.

  2. 2.

    The previously unknown 1,2-bis(1-carboxymethylcyclohexyl)ethane and its dimethyl ester, and dispiro[5.2.5.3]heptadecan-16-one and its 2,4-dinitrophenylhydrazone, were obtained.

  3. 3.

    When a H atom in the hydrocarbon chain of a dicarboxylic acid is replaced by CH3 the dihedral angle of rotation around the C1-C2 bond changes by ∼120° for any C1 atom as the result of 1,3-interactions.

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Literature cited

  1. W. H. Carothers and J. W. Hill, J. Amer. Chem. Soc.,55, 5043 (1933).

    Google Scholar 

  2. M. Stoll and A. Rouvé, Helv. Chim. Acta,27, 1570 (1944).

    Google Scholar 

  3. V. I. Yakerson and A. M. Rubinshtein, Reactions and Methods for the Study of Organic Compounds [in Russian], Vol. 13, Khimiya, Moscow (1964).

    Google Scholar 

  4. A. L. Liberman, T. V. Vasina, and Z. Z. Novikova, Izv. Akad. Nauk SSSR, Ser. Khim., 1527 (1971).

  5. A. L. Liberman, T. V. Vasina, and Z. Z. Novikova, Izv. Akad. Nauk SSSR, Ser. Khim., 1917 (1971).

  6. A. L. Liberman and T. V. Vasina, Dokl. Akad. Nauk SSSR,198, 1344 (1971).

    Google Scholar 

  7. R. M. Beesley, C. K. Ingold, and J. F. Thorpe, J. Chem. Soc.,107, 1080 (1915).

    Google Scholar 

  8. A. L. Liberman and T. V. Vasina, Zh. Organ. Khim.,3, 690 (1967).

    Google Scholar 

  9. N. L. Allinger, J. Amer. Chem. Soc.,81, 5727 (1959).

    Google Scholar 

  10. F. R. Jensen, D. S. Noyce, C. H. Sederholm, and A. J. Berlin, J. Amer. Chem. Soc.,84, 386 (1962).

    Google Scholar 

  11. A. I. Vogel, J. Chem. Soc., 1758 (1934).

  12. M. Qudrat-I-Khuda, J. Chem. Soc., 713 (1929).

  13. S. F. Birch, V. E. Gripp, D. T. McAllan, and W. S. Nathan, J. Chem. Soc., 1363 (1952).

  14. A. L. Liberman and T. V. Vasina, Dokl. Akad. Nauk SSSR,189, 1021 (1969).

    Google Scholar 

  15. A. L. Liberman and T. V. Vasina, Izv. Akad. Nauk SSSR, Ser. Khim., 632 (1968).

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    A. L. Liberman & T. V. Vasina

Authors
  1. A. L. Liberman
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  2. T. V. Vasina
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 854–858, April, 1975.

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Liberman, A.L., Vasina, T.V. Cycloketonization and linear polyketonization of α, ω-dicarboxylic acids. Russ Chem Bull 24, 771–775 (1975). https://doi.org/10.1007/BF00920691

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  • DOI: https://doi.org/10.1007/BF00920691

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