Oxygen-stabilized carbocations (oxocarbenium ions) are important intermediates in synthetic chemistry and glycobiology. Consequently, a deeper understanding of their structures and reactivities would benefit both fields.  Our research demonstrates that electronic effects exert powerful influences on the conformational preferences of these cations. Furthermore, nearby functional groups that can engage in neighboring-group participation may or may not be involved in the rate- and stereochemistry-determining steps of these reactions. As the nucleophile becomes more reactive, stereoselectivity can increase, decrease, or remain the same, which provides information regarding the structures and reactivities of intermediates. The insight gained from these studies can also explain the selectivities of reactions of carbonyl compounds with nucleophiles such as Grignard reagents.

Stereoselective addition reactions to carbon electrophiles: Conformational analysis, stereoelectronic effects, and reactivity

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.