This research addresses two distinct areas of synthetic organic chemistry: the use of phase transfer catalysts for the fluoroalkoxylation of activated haloaromatic and haloheteroaromatic systems, as well as the Grignard addition and sodium cyanoborohydride reduction of aryl chloropropeniminium salts. In Part I of this research, a number of macrocyclic- and linear polytethers were studied as phase transfer catalysts in the nucleophilic aromatic substitution of haloaromitc systems. The most effective catalyst was determined to be poly(ethylene glycol)-8000 and the reaction conditions were optimized for this catalyst. Subsequently isomer reactivity, effects of activating groups, effects of leaving groups, and nucleophiles were studied with respect to the selective fluoroalkoxylation of various halogenated aromatic substrates. In Part II, a series of 3-chloro-3-aryl-prop-2-en-lyliden-dimethyliminium perchlorates were synthesized, isolated, and subsequently their regio-chemistry was studied with reducing agents and with Grignard reagents. The results indicated that reduction and Grignard addition occurred at the imine (C=N) carbon to form the corresponding N, N-dialkyl allylic amines.
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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)
Moebus, Martin A.M., "I. The Use of Polyethers as Phase Transfer Catalysts for the Fluoroalkoxylation of Halogenated Aromatic and Heteroaromatic Systems II. The Grignard Addition and Sodium Cyanoborohydride Reduction of Arylchloropropeniminium Salts" (1985). Retrospective Theses and Dissertations. 4829.
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