Date of Award
Master of Science
James Kiddle, Ph.D.
Elke Schoffers, Ph.D.
Gellert Mezei, Ph.D.
Organocatalysis, epoxidation, chalcone, amino acids, chemistry
Masters Thesis-Open Access
The epoxide functional group is important throughout the chemical and pharmaceutical industries, as well as in nature. In the chemical industry, epoxides are present in resins and fragrances. In the pharmaceutical industry, epoxide-containing compounds are used as intermediates in the manufacturing of drugs. In nature, many natural products contain epoxide groups and are used for medicinal purposes, and for models to create synthetic molecules.
One approach to epoxide synthesis involves the use of an alkene precursor, a base, and an oxidizing agent. This is where my investigations began. The first step was to optimize the epoxidation reaction, examining substrate scope, catalysts, oxidizing agents, solvents, bases, reaction times, and temperatures. The optimized epoxidation reaction involves chalcone as a substrate, with water as a solvent and proline as a catalyst.
The work continued by synthesizing various substituted chalcones, which were used in epoxide formation investigations. It was found that reactions with substituents on the R1 side of the chalcone were unsuccessful, while those on the R2 side were successful. This indicates that substituents on the R1 side of the chalcone electronically influence the oxygen of the ketone, thereby inhibiting the formation of the reaction intermediate, and therefore the overall reaction, while those on the R2 side do not have this effect. Changing the structure of the molecule away from a chalcone also inhibited the formation of the epoxide product.
Kegeler, Sabrina N., "Organocatalyzed Synthesis of Epoxides from Chalcones Utilizing Amino Acids" (2018). Master's Theses. 3418.