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Preparation Of 2,5-Diaryl-1,3,4-Oxadiazoles, Joachim D. Dobe

Retrospective Theses and Dissertations

This report regards the research conducted in the synthesis of 2,5-disubstituted-1,3,4-oxadiazoles as potential insecticides which are closely related to the known insecticide DOWCO 416^R, 2,5-bis(2,4-dichlorophenyl)-1,3,4-oxadiazole. The following compounds were synthesized: 2-(2,4-dichloro-5-nitrophenyl)-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole, (2-(2,4-dichloro-5-nitrophenyl)-5-phenyl-1,3,4-oxadiazole, 2-(2,4-dichloro-5-aminophenyl)-5-aminophenyl)-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole and 2-(2,4-dichloro-5-aminophenyl)-5-phenyl-1,3,4-oxadiazole.

From the commercially available starting material, 2, 4-dichlorobenzoic acid, preparation of the above compounds involved nitration, reduction, esterification, preparation of monoacylhydrazines, preparation of substituted diacylhydrazines and preparation of 2, 5-disubstituted-1, 3, 4-oxadiazoles. All these compounds were characterized via NMR and infrared spectroscopy. In addition, this report includes discussion and recommendations concerning the experimental procedures and conditions for the preparation of these compounds.