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Date of Award
Restricted Thesis: Campus only access
Bachelor of Science
Dr. Wade Downey
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.
Sklar, Danielle, "Synthesis of 2-Methylfurans Through Alkylation-Cyclization-Aromatization Reactions" (2020). Honors Theses. 1513.