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Cyclic unsaturated compounds Communication 51. direction of lactonization of bicyclo[2.2.1]-2-heptene-5,6-dicarboxylic acids

  • E. P. Prokof'ev
  • L. I. Petrovskaya
  • V. A. Mironov
Organic and Biological Chemistry

Conclusions

  1. 1.

    A study was made of the NMR spectra of some methyl-substituted lacto esters that are derivatives of the acids that are formed in the spontaneous lactonization of the correspondingbicyclo[2.2.1]-2-heptene-5.6-dicarboxylic acids.

     
  2. 2.

    In the mentioned acids with a monosubstituted double bond the closure of the γ-lactone ring is accomplished at the C2-center (containing the substituent). In the acids with a disubstituted double bond the substituent at C3 in the formed lactones assumes an exo-configuration.

     
  3. 3.

    Additional proof was obtained for the endo-configuration of the anhydride ring in the adducts of substituted cyclopentadienes with maleic anhydride, and in the case of the 5-substituted cyclopentadienes, for the syn-configuration of the substituent at the C7-center (at the bridge) in the adducts that predominate in the corresponding mixtures of the stereoisomers.

     

Keywords

Ester Adduct Double Bond Anhydride Lactone 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Consultants Bureau 1973

Authors and Affiliations

  • E. P. Prokof'ev
    • 1
  • L. I. Petrovskaya
    • 1
  • V. A. Mironov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryUSSR

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