This report discusses the research conducted in two areas: the synthesis of potential insecticides and the investigation of vinamidinium and azavinamidinium salt chemistry. Firstly, four classes of compounds were synthesized and characterized in the investigation of new potential insecticides. These classes of compounds include a-formamidine methyl esters, amidines, diacylhydrazines and 2,5-disubstituted-1,3,4-oxadiazoles and were characterized via NMR and infrared spectroscopy. This account also reveals and discusses the experimental conditions and procedures necessary for the preparation of these potential insecticides. Secondly, the reaction of [ 3-(dimethyl amino)-2-azaprop-2-en-1-ylidene] dimethyl ammonium chloride (Gold's Reagent) with nucleophiles such as activated (nitro) methylene compounds was examined in hopes of obtaining a more economical process for the production of indoles. Optimum reaction conditions were determined to an extent with regard to solvent, base and temperature. In addition, the reduction of vinamidinium salts was examined using numerous reducing agents; however, only sodium borohydride and sodium cyanoborohydride were found to yield unique products, that is, N,N-dimethylallylic amines and 2-aryl-3-cyanoenamines, respectively. Hence, this report also discloses the experimental conditions and procedures responsible for the novel synthesis of these products, and offers a probable mechanism for their formation. Finally, this report briefly explains the data, and offers recommendations for further research.
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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)
Lizzi, Michael J., "Synthesis of Potential Insecticides and New Synthetic Applications of Vinamidinium and Azavinamidinium Salts: Reactions with Reducing Agents and Nitro Compounds" (1982). Retrospective Theses and Dissertations. 641.