Protonated (protosolvated) onium ions (onlum dications) |
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Authors: | G. A. Olah G. K. Surya Prakash P. Donald Katherine B. Loker Koop Lammertsma |
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Affiliation: | 1. Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 90089-1661, Los Angeles, California, USA 2. Department of Chemistry, University of Alabama at Birmingham, 35294, Birmingham, Alabama, USA
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Abstract: | In this short review we have shown the importance of protosolvation of onium ions (containing non-bonded pairs of electrons) in superacid catalyzed reactions. Such activation can result in unusual reactions such as aromatic alkylation with Meerwein’s salts, aliphatic nitration with nitronium ion, alkylation of saturated hydrocarbons, greatly enhanced activity of acyl cations, etc. Possibly such phenomena may be operative in hydroxylation reactions using protonated hydrogen peroxide in strong acid solutions. Even the reactivity of halonium ions could be enhanced by protosolvation. Consequently, electrophilic protosolvation may play a significant role in strogg acid catalyzed reactions. |
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