ิThese forces
are not balanced for the alkoxy-substituted oxocarbenium ion,
however. Alkoxy substituents exhibit a larger preference for the
pseudoequatorial conformer than the alkyl-substituted cation,24
likely due to hyperconjugation between the electron-donating
C-H bond and the 2p orbital on the electrophilic carbon atom.5
Because an alkoxy group is less sterically demanding than an
alkyl group, the nucleophile can approach from the same face as
the substituent to provide predominantly the 1,2-cis product 14b.
As with the 3-substituted oxocarbenium ion, cis selectivity is
inconsistent with anchimeric assistance