Abstract
The stereochemical structure of the cycloaliphatic epoxy monomer, 4-vinylcyclohexene oxide (VCO), was determined using 13C NMR spectroscopy and quantum chemical calculation. The 13C 2D INADEQUATE NMR spectrum of VCO showed that this compound is composed of 4 stereochemical isomers. Although NMR spectroscopy is unavailable to identify the structure of the isomers, the isomeric energy calculations using the MNDO method lead to the complete structural determination of them. Among 8 isomers in terms of the bond connecting cyclohexene oxide ring and ethylene oxide ring, the equatorial forms were considerably more stable than the axial forms. Thus the former were isomers found in the 13C NMR spectrum of VCO. In addition, the isomeric composition was obtained from the signal intensity of the NOE-suppressed 13C NMR spectrum.
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Udagawa, A., Yamamoto, Y., Inoue, Y. et al. Structural Determination of 4-Vinylcyclohexene Oxide Using 2D INADEQUATE NMR Spectroscopy and MNDO Calculation. Polym J 22, 719–723 (1990). https://doi.org/10.1295/polymj.22.719
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DOI: https://doi.org/10.1295/polymj.22.719