Investigation of Reactive Intermediates and Inner Phase Reactions Inside Molecular Container Compounds

This project has the long term objective to apply molecular container compounds in areas such as the characterization of reactive intermediates and in catalysis. Two highly strained cyclic allenes and various intermediates in the naphthylcarbene rearrangement will be generated and spectroscopically characterized in the inner phase of hemicarcerands, and their thermochemistry will be investigated. These species are important to structural theory in organic chemistry. In addition, a new approach for the stabilization of reactive intermediates will be developed. This approach involves the covalent bonding of a precursor molecule on the inside of a hemicarcerand, whereupon generation of a reactive intermediate from this precursor takes place to the exclusion of other reactive species. Quenching of the intermediate is thus prevented.

With this award, the Organic and Macromolecular Chemistry Program's Organic Dynamics Program supports the research of Professor Ralf Warmuth of Kansas State University. Professor Warmuth is pursuing an area of physical organic chemistry wherein chemical species that are implicated as intermediates in reaction processes are created and observed. These species are referred to as reactive intermediates, and are normally so short-lived that direct observation is difficult. By forming these intermediates in a protective shell, Professor Warmuth will be able to extend the lifetimes of these elusive entities, making their observation more feasible.