Enolate Aggregation and Reactivity

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With this renewal award the Organic and Macromolecular Chemistry Program is continuing its support for the work of Dr. Andrew Streitwieser of the Department of Chemistry of the University of California at Berkeley. The research aims to extend earlier work on the equilibria and kinetics involved in the aggregation of lithium enolates and their reactions with organic halides, sulfonates, and carbonyl compounds containing activated double bonds. Variables to be explored include steric effects, conjugation, added functionality which can coordinate with the lithium ions, solvent effects, and the effects of additives such as HMPA and amines. Research, which involves dilute air-sensitive solutions, will be done in a unique glove box facility, with a thermostated sample holder connected by quartz fiber-optic cables to an external computer-controlled uv/vis spectrometer. Experiments will be complemented by theoretical computations. The increased understanding expected to result from this work will aid synthetic chemists to devise improved ways to form organic molecules containing new carbon-carbon bonds.