Probing the arenium-ion (protontransfer) versus the cation-radical (electron transfer) mechanism of Scholl reaction using DDQ as oxidant

L Zhai, R Shukla, SH Wadumethrige…

Index: Zhai, Linyi; Shukla, Ruchi; Wadumethrige, Shriya H.; Rathore, Rajendra Journal of Organic Chemistry, 2010 , vol. 75, # 14 p. 4748 - 4760

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Citation Number: 99

Abstract

DDQ/H+ system readily oxidizes a variety of electron donors with oxidation potential as high as∼ 1.7 V to the corresponding cation radicals. A re-examination of the controversial arenium-ion versus cation-radical mechanisms for Scholl reaction using DDQ/H+ together with commonly utilized FeCl3 as oxidants led us to demonstrate that the reaction proceeds largely via a cation-radical mechanism. The critical experimental evidence in support of a ...