Ammonium salts, Chemical reactions, Organic compounds -- Synthesis
This report discusses research involving the reactions of 2-arylprop-1-en-3-yltrimethyl ammonium iodides with sulfur nucleophiles and the useful synthetic applications of the adducts formed. The present work may be subdivided into four sections: 1) reactions of several 2-arylprop-1-en-3-yltrimethylammonium iodides with benzenethiol; 2) reactions of several 2-arylprop-1-en-3-yltrimethylammonium iodides with the sodium salt of benzenesulfinic acid; 3) reactions of several 2-arylprop-1-en-3-yltrimethylammonium iodides with 2-mercapto-1-methyl imidazole; and 4) oxidation of 2-aryl-3-phenylthio-1-propenes and 2-aryl-3-phenylsulfonyl-1-propenes using sodium perborate. This report outlines the experimental conditions and procedures responsible for the synthesis of these products; in addition, this report describes the physical properties, NMR and IR spectra of the compounds synthesized, as well as offers a possible mechanism for their formation. The classes of compounds synthesized include: 2-aryl-3-phenylthio-1-propenes; 2-aryl3-phenylsulfonyl-1-propenes; 3-(2-aryl-l-propenyl)2-(1-methylimidazoyl)thioethers; and 2-aryl-2-acetoxy-3-phenylsulfonyl-1-propanols. Recommendations are listed to suggest future research in this area.
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Gupton, John T.
Master of Science (M.S.)
College of Arts and Sciences
Length of Campus-only Access
Doctoral Dissertation (Open Access)
Duranceau, Steven J., "The Reaction of 2-Arylprop-1-En-3-Yltrimethylammonium Iodides With Sulfur Nucleophiles and Useful Synthetic Applications of These Adducts" (1987). Retrospective Theses and Dissertations. 5040.
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