Addition of organic halogen compounds

Halo-substituted unsaturated hydrocarbons behave like aromatic hydrocarbons towards saturated halides in the presence of aluminum chloride.93 Suitable acceptors are the halogen substitution products of ethylene in particular, chloromethanes, and best of all chloroform and methylene chloride 

The reaction of isopropyl chloride with trichloroethylene has been described by Schmerling95 who gives also other examples. The halogen atom adds to the carbon atom carrying the smaller number of hydrogen atoms iron(m) chloride can be used as catalyst as well as aluminum chloride 96 Schmerling also added variously branched alkyl halides to ethylene, obtaining, e.g., a 75% yield of l-chloro-3,3-dimethylbutane from tert-butyl chloride and ethylene 97 

Radical addition of halo methanes to olefins was achieved by Kharasch and his co-workers98,99 when they warmed a mixture of an olefin with, e.g., carbon tetrabromide or an excess of carbon tetrachloride in the presence of 1-5 mole % of a diacyl peroxide at 70-90°  

Carbon tetrabromide adds when irradiated even without addition of a peroxide catalyst.100 

Kharasch et al. also achieved peroxide-catalysed addition of a-bromo fatty acid esters, thus obtaining y-bromo fatty acid esters 99,101 

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