Abstract
Abstract The conformational analysis of a stereoisomeric pair of 4-hydroxymenthones, (1R:4R)-(−)-4-hydroxymenthone (1) and (1R:4S)-(+)-4-hydroxyisomenthone (2), was made by means of temperature-dependent circular dichroism. It was demonstrated that α-hydroxyketone (1) exists in the conformational equilibrium: 1a\leftrightarrows1b; the conformer 1a exists predominantly in a nonpolar medium, whereas the conformer 1b is more stable than 1a in a polar medium. On the other hand, the other isomer, (2), exists preferentially in the state of the conformer 2b in either a polar or a nonpolar solvent. The results were interpreted in terms of the competition of the steric factor and intramolecular hydrogen-bonding.
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