Organic Reactions and Syntheses in Water Solution

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Professor Ronald Breslow, of the Department of Chemistry at Columbia University, is supported by the Organic Synthesis Program for his studies of organic reactions and synthesis in water solution. In addition to the environmental advantages of carrying out chemical reactions in water instead of organic solvents, water can also influence the effectiveness of organic reactions. Thus, for example, the Diels Alder reaction is found to be both faster and more selective when carried out in aqueous solution. Professor Breslow explores the factors influencing such chemical reactions, focusing on hydrophobic effects and on polarity issues. He also exploits the hydrophobic effect in designing cyclodextrin-based catalysts and is developing additional non-cyclodextrin-based synthetic binding agents which also rely on hydrophobic binding. His synthetic bifunctional catalysts permit the determination of the preferred reaction geometries for such reactions as the deprotonation of carbon during enolization. With the support of the Organic Synthesis Program, Professor Ronald Breslow, of the Department of Chemistry at Columbia University, explores chemical reactions in water in place of traditional organic solvents. While the use of water offers clear and significant environmental advantages, it plays a central chemical role as well. Thus, certain chemical reactions are found to be greatly accelerated when carried out in aqueous solution, and they often lead more selectively to specific products. These effects appear to be due, at least in part, to the tendency of many organic molecules to aggregate in water so as to minimize their interfaces with the water solvent. Professor Breslow exploits similar effects in the design and construction of molecules which bind smaller molecules in solution and then carry out desired chemical transformations of the bound molecules, mimicking in many ways the function of enzymes. These studies are leading to an understanding of the factors controlling certain chemical reactions.