Structure and Reactivity of Mixed Aggregates of Lithium Alkyls and Alkoxides

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This project by Craig Ogle of the University of North Carolina, Charlotte is within the Organic Dynamics Program, and is aimed at a better understanding of organolithium compounds. Organolithiums are important intermediates in the synthesis of a wide variety of organic compounds, and this research will provide the elucidation of their structure by a relatively new technique known as rapid injection nuclear magnetic resonance spectroscopy. The reactivity of alkyllithium reagents is often modified by the addition of alkoxides. Mixed bases have been used extensively in metalations, polymerizations and alkylations, without a clear understanding of how the reagent is being changed. This study is aimed at providing a fundamental understanding of the mechanism of the reaction of alkyllithiums and mixed aggregates with electrophiles; this may lead to the development of more reactive and selective reagents. The work will consist of the preparation and identification of mixed aggregates of organolithiums and alkoxides of groups IA and IIA. The reactivity of these mixed aggregates towards electrophiles and carbon acids will then be investigated by Li-7 and H-1 rapid injection NMR. Mixed aggregates formed from the reaction of alkyllithiums with electrophiles will also be investigated.