Journal of Undergraduate Research


electronic structure, quassiclassical dynamics, tetrafluoroethylene cycloaddition reactions


Life Sciences


Chemistry and Biochemistry


Cycloaddition reactions are key reactions used to construct complex cyclic scaffolds (large networks of carbon atoms that can be used in catalysis, synthesis, etc.). While classical reactions that form 6-membered rings are well-known and generally have a one-step reaction mechanism, 4-member ring-forming reactions are much less used, but could be very valuable for the construction of cyclobutane structures.

Tetrafluoroethylene (TFE) is used on a large scale by Dow and other chemical companies to form hydrofluoro compounds such as teflon. The current understanding of the mechanism of cycloaddition reactions with TFE is limited. Standard hydrocarbon reactions proceed via a welldocumented, concerted mechanism known as the Diels-Alder reaction; however, the addition of electron-withdrawing groups has been demonstrated to change the selectivity of these reactions, and the mechanism by which they proceed is as yet unknown. Specifically, cycloaddition between 1,3-butadiene and TFE results in exclusive formation of a 4 membered ring with a 2- carbon tail, as opposed to the 6 membered ring structure that is expected with similar cycloaddition reactions. Understanding the mechanism and periselectivity of these cycloaddition reactions will provide a long-standing resolution to many reactions and could lead to the development of new reactions with TFE.