Interception of deaminatively generated benzyl carbenium ions by acetone

F Song, RW Darbeau, EH White

Index: Song, Fenhong; Darbeau, Ron W.; White, Emil H. Journal of Organic Chemistry, 2000 , vol. 65, # 6 p. 1825 - 1829

Full Text: HTML

Citation Number: 14

Abstract

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 ...