Controlling factors determining the regiochemistry of intramolecular alkoxymercuration
Abstract
The intramolecular alkoxymercuration of
(E
)-5-arylpent-4-en-1-ols indicated that the
regioselectivity is closely related to the Hammett constants of the
para-substituents on the benzene ring. Large solvent effects on
the regioselectivity were also observed. These results were compared
with those of the methoxymercuration of β-methylstyrene analogues.
The regioselectivity is discussed in terms of steric effects as well as
the electronic effects which are suggested by the MO calculation for the
mercurinium ion intermediates.
)-5-arylpent-4-en-1-ols indicated that the
regioselectivity is closely related to the Hammett constants of the
para-substituents on the benzene ring. Large solvent effects on
the regioselectivity were also observed. These results were compared
with those of the methoxymercuration of β-methylstyrene analogues.
The regioselectivity is discussed in terms of steric effects as well as
the electronic effects which are suggested by the MO calculation for the
mercurinium ion intermediates.
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