Optical Rotatory Dispersion Studies. 130. Additivity of Deuterium Octant Contributions in Cyclohexanone

Article abstract of DOI:10.1021/jo01301a027

A comparison between the circular dichroism spectra of (4S)-3,3-dideuterio-4-methylcyclohexanone (1), (3R,4R)-3-deuterio-4-tert-butylcyclohexanone (2) and (3S,4R)-3-deuterio-4-tert-butylcyclohexanone (3) leads to the conclusion that the octant contributions of deuterium in the β-equatorial and β-axial positions of the cyclohexanone ring are additive.From the temperature-dependent circular dichroism spectra of 1 an energy difference of -1.1 kcal/mol was obtained for the conformations with the 4-methyl substituent in the axial and equatorial position, respectively.