Axial Preference of Bulky Group- and Electron-Withdrawing Group-Substituted Oxygen Atom on the Chair-Type-Cyclohexanone, -Glutaric Anhydride, and -Glutarimide

Article abstract of DOI:10.1246/cl.1990.1503

Axial preference (> ca. 70percent at 25 deg C) of alkoxy and silyloxy groups of the chair-type six-membered cyclic compounds has been clarified by the 1H-NMR bandwidth measurement method.Based on the X-ray analysis of 4-substituted cyclohexanones, it has been disclosed that the cyclohexanone ring adopts chair form and the 4-substituent occupies the axial site in all cases.