Regio- and stereoselectivity in the solvomercuriation and intramolecular alkoxymercuriation of cyclic unsaturated alcohols

The regio- and stereoselectivity in the solvomercuriation and intramolecula r alkoxymercuriation of several cyclic olefinic alcohols were examined. The regioselectivity is controlled mainly by electronic factors, while the ste reoselectivity is controlled by steric factors as well as electronic ones. The optimised structure of the mercurinium ion intermediate suggests that t he attractive interaction between the hydroxy group in the molecule and the mercurinium ion moiety affects the selectivity.