Abstract
The relative rate constants for SiH hydrogen abstraction from substituted phenylsilanes, phenylmethylsilanes and phenyldimethylsilanes by the trichloromethyl radical have been determined from competitive chlorinations at 80° with carbon tetrachloride as the chlorinating agent. The relative rates for the three sets of arylhydrosilanes are well correlated with the Hammett σ constants for the ring substituents, with ϱ values of −0.460, −0.372 and −0.453, respectively. It seems that there is electrophilic attack by the trichloromethyl radical at the SiH bond but without much separation fo charge in the transition state. The ϱ values are compared with those for the benzylic hydrogen abstraction from the corresponding carbon analogs.
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