Generation, Study, and Application of Dicationic Intermediates

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Generation, Study, and Application of Dicationic Intermediates Douglas A. Klumpp, Department of Chemistry, Northern Illinois University, DeKalb, IL 60115 During the past two years, we have exploited the high reactivities of dicationic, superelectrophilic intermediates in the development of new synthetic methodologies. Some of these conversions are shown below. Besides the new synthetic methodologies, the work has also provided key insights into the chemistry of these reactive, highly charged intermediates. Superacid-promoted reactions of a-keto and b-ketoamides: J. Org. Chem. 2008, 73, 6506-6512; 2007, 72, 9761-9764 Synthesis of polycyclic aromatic compounds: J. Org. Chem. 2008, 73, 3654-3657 Aza-Nazarov reaction: Org. Lett. 2007, 9, 3805-3809 Single electron transfer (SET) reactions with superelectrophiles: J. Am. Chem. Soc., manuscript in revision