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Beneficial role of conformational 1,3-interactions in acyloin condensation reactions of esters of some branched dicarboxylic acids

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The yields of acyloins in acyloin condensation reactions are quite dependent on the presence of 1,3-interactions of the side chains with the H atoms of the backbone chain of the starting dicarboxylic acid esters. Contrary to the literature data, the gem effect has a comparatively small role in this reaction.

  2. 2.

    We synthesized 4-methylpimelonitrile, 5-methylazelaic acid and its dimethyl ester, and 4.8-dimethylcyclononanol-2-one.

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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, S. A. Chelmakova & V. N. Lutovinova

Authors
  1. A. L. Liberman
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  2. T. V. Vasina
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  3. S. A. Chelmakova
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  4. V. N. Lutovinova
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No.1, pp.187–190, January, 1976.

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Liberman, A.L., Vasina, T.V., Chelmakova, S.A. et al. Beneficial role of conformational 1,3-interactions in acyloin condensation reactions of esters of some branched dicarboxylic acids. Russ Chem Bull 25, 178–180 (1976). https://doi.org/10.1007/BF00925648

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  • DOI: https://doi.org/10.1007/BF00925648

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