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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, solvolysisconstants of model compounds can be used to predict the outcome of any such addition reactions if systems withconsiderable steric hindrance are excluded.

the journal of organic chemistry

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