Organic Reactions and Syntheses in Water Solution

With funding from the Organic Dynamics Program Professor Breslow of Columbia University will develop methods that cause organic reactions to occur in water solutions. Organic molecules will be incorporated into cyclodextrin cavities and these complexes will be dissolved in aqueous solutions. This technique will allow the study of the effects of water on normally hydrophobic reactions of organic compounds. Cyclodextrins will be modified to contain by covalent bonds biphasic organic catalysts whose ability to accelerate certain organic reactions in the presence of metal ions will be studied. The use of selected cyclodextrins will also allow the determination of specific geometry requirements that are anticipated to occur in selected organic reactions. The goals described in the proposal are applicable to the area of environmentally chemically benign synthesis. This research will use the unique shapes of naturally occurring cyclodextrins, found in plants rich in starch, as miniature containers in which certain organic reactions will occur while the entire mixture is dissolved in water. Many organic substances resist interacting with water and exhibit hydrophobic behavior. The use of cyclodextrins as containers which dissolve in water will allow a unique study of the hydrophobic reactivity of organic compounds in a water environment. This research represents an important development of environmentally benign chemical synthesis studies that can help to reduce pollution from manufacturing processes in the chemical industry.