Unexpected formation of the most strained δ-lactone in the pyrolysis of diethyl ester of <i>cis</i>-4-hydroxy-<i>trans</i>-5-methoxy-<i>trans</i>-1,2-cyclohexanedicarboxylic acid

Authors

  • B. А. Чертков M. V. Lomonosov Moscow State University, Moscow 119899
  • Е. K. Добрецова M. V. Lomonosov State Academy of Fine Chemical Technology, Moscow 117571
  • Д. Е. Гремячинский M. V. Lomonosov Moscow State University, Moscow 119899
  • С. С. Голотвин M. V. Lomonosov Moscow State University, Moscow 119899
  • H. А. Симонов M. V. Lomonosov State Academy of Fine Chemical Technology, Moscow 117571
  • Л. П. Вaтлина M. V. Lomonosov Moscow State University, Moscow 119899
  • B. B. Сaмoшин K. D. Ushinskii Yaroslavl' State Pedagogical University, Yaroslavl' 150000

Abstract

Vacuum distillation of diethyl ester of cis-4-hydroxy-trans-5-methoxy-trans-1,2-cyclohexanedicarboxylic acid gave a single compound, 5-ethoxycarbonyl-7-methoxy-2-oxa[2.2.2.]bicyclooctan-3-one. The structure of this δ-lactone was demonstrated by data of NMR and IR spectroscopy. Calculations using the method of molecular mechanics showed that this structure has the highest steric strains of all possible stereoisomeric δ-lactones.

How to Cite
Chertkov, V. A.; Dobretsova, E. K.; Gremyachinskii, D. E.; Golotvin, S. S.; Simonov, N. A.; Vatlina, L. P.; Sasmoshin, V. V. Chem. Heterocycl. Compd. 1997, 33, 33. [Khim. Geterotsikl. Soedin. 1997, 41.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02290743

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Published

1997-01-25

Issue

No. 1 (1997)

Section

Original Papers