Abstract
A 1H NMR conformational study of cis- and trans-4-substituted cyclohexene oxides revealed an increased predominance, as compared with the parent 4-substituted cyclohexenes, of the equatorial conformer for cis-isomers and a preference of the axial conformer for trans-isomers. These conformational shifts can be rationalized in terms of intramolecular dipole-dipole and/or steric interactions. However, molecular mechanics calculations failed to reproduce the relative stability of the axial conformer in trans-4-substituted cyclohexene oxides.
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