Friedel-Crafts-type reactions involving di-and tricationic species. Onium-allyl dications and O, O-diprotonated aci-nitro species bearing a protonated carbonyl group

T Ohwada, N Yamagata, K Shudo

Index: Ohwada, Tomohiko; Yamagata, Naoko; Shudo, Koichi Journal of the American Chemical Society, 1991 , vol. 113, # 4 p. 1364 - 1373

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Citation Number: 84

Abstract

Abstract: Stable carbocations do not react with nonactivated benzenes. For example, acetophenone does not react with benzene in the presence of trifluoromethanesulfonic acid (TFSA), while trifluoroacetophenone does do so under acidic conditions owing to activation of the electrophilicity of the hydroxycarbenium cation by the trifluoromethyl group. This and other studies suggest that an electron-withdrawing substituent on the cationic center ...