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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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M. V. Lomonosov Moscow State University, Moscow 119899. M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, Moscow 117571. K. D. Ushinskii Yaroslavl' State Pedagogical University, Yaroslavl' 150000. Translated from Khimiya Geterotsiklicheskaya Soedinenii, No. 1, pp. 41–47, January, 1997.

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Chertkov, V.A., Dobretsova, E.K., Gremyachinskii, D.E. et al. Unexpected formation of the most strained δ-lactone in the pyrolysis of diethyl ester of cis-4-hydroxy-trans-5-methoxy-trans-1,2-cyclohexanedicarboxylic acid. Chem Heterocycl Compd 33, 33–38 (1997). https://doi.org/10.1007/BF02290743

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  • DOI: https://doi.org/10.1007/BF02290743

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