Honors Theses
Date of Award
Spring 5-7-2026
Document Type
Undergraduate Thesis
Department
Chemistry and Biochemistry
First Advisor
David A Colby
Second Advisor
Jonah Jurss
Third Advisor
Antim Maurya
Relational Format
Thesis
Abstract
As the most electronegative element, fluorine has unique applications and properties. The carbon-fluorine bond is known to be one of the strongest bonds in organic chemistry. As a result of fluorine’s high C–F bond strength, fluorine chemistry has become an interdisciplinary field of chemistry, pharmacy, physics, geology, and ecology. In pharmaceuticals for example, current estimates indicate that about 15–20% of FDA approved small-molecule drugs include at least one fluorine atom. The incorporation of fluorine atoms into organic molecules has become a powerful strategy in modern drug development, as fluorination can enhance metabolic stability, lipophilicity, and biological activity. Despite these advantages, the synthesis of highly fluorinated compounds remains challenging due to the difficulties of making the C–F bond and the electronic effects imparted by fluorinated substituents.
Building upon previous work in the Colby laboratory demonstrating the high-yield synthesis of difluoromethyl ketones from α-fluorinated gem-diols, this project aimed to develop novel tetrafluorinated alcohols through the dimerization of difluoromethyl ketones. Using LiBr and Et3N to promote the release of trifluoroacetate from α-fluorinated gem-diols with base, multiple tetrafluorinated alcohol derivatives were synthesized by dimerization and purified. The reaction conditions were optimized to improve yield and minimize byproduct formation. This work expands the synthetic utility of α-fluorinated intermediates and provides access to structurally complex, highly fluorinated alcohols that may serve as valuable scaffolds in medicinal chemistry and future drug development.
Recommended Citation
Ryan, Abigail A., "Synthesis of Novel Tetrafluorinated Alcohols Through the Dimerization of Difluoromethyl Ketones for Use in Drug Development" (2026). Honors Theses. 3611.
https://egrove.olemiss.edu/hon_thesis/3611