The majority of C-C bond forming reactions involve the interaction of electrophilic carbon species with carbanionic centers, of which organolithium reagents are probably the most important source. The vast organolithium literature provides a great deal of empirical information, but firm mechanistic and structural insights have been difficult to achieve.  We have attempted to understand in detail the properties and reactions of organolithium reagents using reactivity, kinetics, stereochemical  and selectivity studies, as well as multinuclear NMR spectroscopic studies using Rapid Injection NMR.  Our efforts have focused on the role played by the various aggregates and mixed aggregates of lithium reagents which are now known to be almost invariably involved in their reactions with electrophiles.

Award Address  (James   Flack Norris Award in Physical Organic Chemistry sponsored by the ACS   Northeastern Section). Structure and reactivity of organolithium reagents

243rd National Meeting (2012)

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