Abstract
Lewis acid promoted additions of alkyl halides, acetals and related compounds to aliphatic Π systems (e.g. Open image in new window ) represent a straightforward method for the formation of CC^bonds, if the consecutive addition of the 1:1 adduct to another alkene molecule can be inhibited. This article describes how the relative electrophili-cities of reactants RX and products PX may be controlled by nature and quantity of the Lewis acid. Model studies on electrophilic additions of diarylmethyl chlorides to alkenes reveal that a catalytic amount of a (weak) Lewis acid has to be used if the reactant RX ionizes to a greater extent than PX, whereas an equimolar amount of a strong Lewis acid is needed if PX ionizes more readily than RX. Examples demonstrating the application range and limitations of these rules are presented.
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