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DOI: 10.1039/A608003K (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1997, 1143-1146

Controlling factors determining the regiochemistry of intramolecular alkoxymercuration

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Yasuhisa Senda, Hiroko Kanto and Hiroki Itoh

Abstract

The intramolecular alkoxymercuration of (E[hair space])-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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