Scope and limitations of aliphatic Friedel-Crafts alkylations. Lewis acid catalyzed addition reactions of alkyl chlorides to carbon-carbon double bonds

Abstract

Lewis acid catalyzed addition reactions of alkyl halides 1 with unsaturated hydrocarbons 2 have been studied. 1:l addition products 3 are formed if the addends 1 dissociate faster than the corresponding products 3; otherwise, polymerization of 2 takes place. For reaction conditions under which 1 and 3 exist mainly undissociated, solvolysis constants of model compounds can be used to predict the outcome of any such addition reactions if systems with considerable steric hindrance are excluded