Off-campus University of Richmond users: To download campus access theses, please use the following link to log in to our proxy server with your university username and password.
Date of Award
2020
Document Type
Restricted Thesis: Campus only access
Degree Name
Bachelor of Science
Department
Chemistry
First Advisor
Dr. Wade Downey
Abstract
Ketones are easily converted to enol silanes in the presence of trimethylsilyl trifluoromethanesulfonate and an amine base, conditions that also result in the ionization of terminally silylated propargyl acetates. When these events occur in a single flask, the intermediates undergo an SN1 reaction to generate a B-propargyl ketone intermediate. Upon concentration in the presence of trace water, the intermediate cyclizes to provide 2- methylfurans in high yield. The use of various ketones and propargyl acetates allows for the synthesis of an extensive range of 2-methylfurans, which can be tested for biological activity.
Recommended Citation
Sklar, Danielle, "Synthesis of 2-Methylfurans Through Alkylation-Cyclization-Aromatization Reactions" (2020). Honors Theses. 1513.
https://scholarship.richmond.edu/honors-theses/1513