Semester of Graduation

Summer 2021


Master of Science (MS)



Document Type



The development of new methodologies in organic chemistry is of great importance. In fact, the discovery and creation of new reactions frequently uncovers new chemical reactivities and creates new areas of chemistry. The purpose of this thesis is to present the development of new synthetic reactions that were discovered through previous findings. Additionally, the main theme of this work relies on the intermediacy of a cationic reactive intermediate: epoxonium ions. Chapter 1 provides a brief review of bicyclic epoxonium ions and methods for their generation, as well as their utility in the synthesis of interesting heterocycles. Furthermore, Chapter 1 illustrates our attempts at applying the information we gained from our group’s previous projects utilizing triphosgene and pyridinium acids for the chemoselective cyclization of epoxides to novel chlorinated pyranoside heterocycles. Ultimately through this study we were able to uncover the unprecedented chemoselective activation of an epoxyketone with triphosgene, as well as discover a novel counterion based selectivity during the ionization of epoxyketones.

Committee Chair

Donghui, Zhang