Electrostatic Effects on the Reactions of Cyclohexanone Oxocarbenium Ions

Nucleophilic substitution reactions of 4-substituted cyclohexanone acetals display different selectivities
depending upon the electronic nature of the substituent. Alkyl groups favor equatorial positions in the
oxocarbenium ions, but alkoxy groups prefer axial conformers. The reactions of acetals with alkoxy
groups constrained to either equatorial or axial positions suggest that the presence of an axial alkoxy
group distorts the oxocarbenium ion, changing its inherent preferences for facial attack.