Abstract
Chlorine-hydrogen exchange reaction between a chloroalkane and a hydrosilane was found to occur under rather mild conditions in the presence of free radical initiators. A radical chain mechanism involving alternate formations of silyl and alkyl radicals was proposed to explain the reduction reaction. For the reaction of carbon tetrachloride with triethylsilane, azobisisobutyronitrile was somewhat less effective than benzoyl peroxide or di-tert-butyl peroxide.
The reduction is very selective. Thus, for example, 1, 2-dichloroethane was obtained from 1, 1, 2-trichloroethane as a sole product. Various chloroalkanes could be reduced in a similar manner and their reactivities appeared to be consistent with the respective carbon-chlorine bond dissociation energies.
The reduction of simple monochloroalkanes is also possible under somewhat drastic conditions.
