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Abstract:
The unsymmetric electron density distribution of the LUMOs of the carbonyl π-bond of cyclohexanones (in the picture C is left, O right) is the reason for preferred axial attack (a) of these compounds by nucleophiles. If the ketones are substituted in the 3-position by electronegative substituents (e.g. halogens), this tendency is enhanced still further. The authors have been able to demonstrate this by quantum mechanical ab-initio calculations.