THE OCTANT RULE. XX. SYNTHESIS AND CIRCULAR DICHROISM OF (1S,5S)-DIMETHYLADAMANTAN-2-ONE -- PREDICTED TO HAVE ZERO COTTON EFFECT

Article abstract of DOI:10.1016/S0040-4020(01)87672-9

The title compound was synthesized in optically active form from adamantane.Although the methyl perturbers lie in the extended local symmetry planes of the carbonyl chromophore, and octant and quadrant rules therefore predict they should make no contributions to the Cotton effect (CE), weak negative CEs are found in cyclopentane (Δε^max₂₉₃ = -0.03) and in CF3CH2OH (Δε^max₂₈₈ = -0.02) solvents.