Determination of the basicities of benzyl, allyl, and tert-butylpropargyl anions by anodic oxidation of organolithium compounds

B Jaun, J Schwarz, R Breslow

Index: Jaun, Bernhard; Schwarz, Joshua; Breslow, Ronald Journal of the American Chemical Society, 1980 , vol. 102, # 18 p. 5741 - 5748

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Citation Number: 109

Abstract

Abstract: Electrochemical oxidation potentials have been determined by using cyclic voltammetry and second-harmonic ac voltammetry for benzyllithium, allyllithium, tert- butylpropargyllithium, and triphenylmethyllithium in tetrahydrofuran/ hexamethylphosphoramide. The use of these potentials along with bond dissociation energies and the known pKa of triphenylmethane permit the estimation of ion-pair ...