Abstract
(S,S)-(+)-3,5-Cyclohexadiene-1,2-diol, (S,S)- 1, displays positive π-π* Cotton effect, Δε +10.0 at 256 nm in methanol. Variable-temperature CD measurements in alcohol solvent indicate that the conformer with equatorial hydroxy groups is more stable than the diaxial one (ΔG° = 0.71 kcal/mol). The diaxial conformer has one order of magnitude higher rotational strength compared to the diequatorial one, due to the effect of the allylic axial CO bonds. The diequatorial conformer is stabilized by electrostatic interactions (MMX calculation) and by intramolecular hydrogen bond formation in non-polar solvents. X-ray diffraction study shows that the diequatorial conformer of (S,S)- 1 is present in the crystalline state.
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