Abstract
Reaction of liquid chlorobenzene or benzonitrile with chlorine under free radical conditions at 100–170° gives, apart from the well known products of additive chlorination, small amounts of dichlorobenzenes and chlorobenzonitriles, respectively. Relative rate and isomer patterns resemble those of the gas-phase, thermal chlorination, known to take place at ca. 300° and above in a flow system. In our opinion this substitution occurs via intermediate aryl radicals, arising through (endothermal) hydrogen abstraction by chlorine atoms.
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