Essentially free benzyl carbenium ions were generated via protonation of phenyldiazomethane with benzoic acid in acetone. Interestingly, no proton transfer occurred below-20° C. After protonation and dediazoniation of the diazoalkane at-20° C, the solvent was found to intercept the deaminatively generated carbocations to yield initially the corresponding O-benzyl oxonium ion and benzyl benzoate. The onium ion, however, was ...
