endo-Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid, in acidic solution, cyclizes to give a mixture of three isomeric lactones. These three isomers have different stabilities and are partly interconvertible, but their simultaneous decomposition makes the experimental study of these equilibria difficult. In the present work, these three lactones were studied using MM3. The relationship between the O-C(O)-C bond angles and the C=O stretching frequencies of these compounds was investigated. Based partly on the thermodynamic data calculated by MM3, the mechanism of the interconversion of the three lactones was proposed.
endo-Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid, in acidic solution, cyclizes to give a mixture of three isomeric lactones. These three isomers have different stabilities and are partly interconvertible, but their simultaneous decomposition makes the experimental study of these equilibria difficult. In the present work, these three lactones were studied using MM3. The relationship between the O-C(O)-C bond angles and the C=O stretching frequencies of these compounds was investigated. Based partly on the thermodynamic data calculated by MM3, the mechanism of the interconversion of the three lactones was proposed.
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