Organogermanium compounds : III. Reduction of substituted benzyl chlorides with triethylgermane

Abstract

The reactivities of seven nuclear-substituted benzyl chlorides relative to that of unsubstituted benzyl chloride in reaction with triethylgermane containing dibenzoyl peroxide in benzene at 80.0° have been investigated. Electron-withdrawing substituents increase the reactivity, and the rates can be correlated by the Hammett equation with a ϱ value of 0.312. It is concluded that the resonance effect ois not important in the transition state, and that the relative rates are governed mainly by polar effects, with the germyl radical behaving as a nucleophile.