Aromatic compounds, Catalysis
This report discusses research which was conducted in two areas: the study of aromatic nucleophilic fluoroalkoxylation assisted via cationic phase transfer catalysis and the study of unsymmetrical vinamidinium salts and their reactions with organometallic reagents. Sodium alkoxides have been successfully used to fluoroalkoxylate activated halo-aryl and heteroaryl substrates under phase transfer catalysis conditions. Optimum reaction conditions incorporated tetra-n-butyl-phosphonium bromide as the catalyst and refluxing toluene as the solvent medium. Different quarternary phosphonium and ammonium salts have been evaluated as catalysts: also, the effects of activating groups, leaving groups, and nucleophiles have been reported. The reaction of 3-dimethylamino-3-phenyl-prop-2-en-1-yliden-dimethyliminium perchlorate with organolithium and Grignard reagents has also been studied in an effort to define the reaction in terms of which electrophilic site of the salt is susceptible to nucleophilic attack to the greatest extent. The results reported reveal that the reaction occurs at the 1-position in all cases producing ∝, β-unsaturated ketone after acid hydrolysis. Finally, this report reveals the experimental procedures used as well as the spectral and physical data of all new compounds synthesized. Explanations of the data are offered and recommendations for future research in both areas are given.
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Gupton, John T.
Master of Science (M.S.)
College of Arts and Sciences
Length of Campus-only Access
Masters Thesis (Open Access)
Coury, Joseph E., "A Two Part Research Report: Aromatic Nucelophilic Fluoroal Koxylation via Cationic Phase Transfer Catalysis and Reactions of Unsymmetrical Vinamidinium Salts with Organometallic Reagents" (1984). Retrospective Theses and Dissertations. 4721.