Thianthrene cation radical induced reactions of semicarbazones and acylhydrazones

dc.creatorMandal, Hari Das
dc.date.available2011-02-18T22:13:05Z
dc.date.issued1996-08
dc.degree.departmentChemistryen_US
dc.description.abstractSingle-electron transfer (SET) reactions of cation radicals have been widely studied." Recently, cation radical induced oxidative intramolecular cyclization reactions and oxidative cycloaddition reactions involving nitrile solvents have been discovered. It was found that cation radicals are capable of causing the oxidative cyclization of arylhydrazones of chalcones and benzalacetones to pyrazoles. In acetonitrile solvent. On the other hand, reactions of thianthrene cation radical with arylhydrazones and oximes of non-conjugated aldehydes in nitrile solvents can cause oxidative cycloaddition to the nitrile group with the formation of 1,2,4-triazoles. Shin investigated the reactions of aldehyde semicarbazones with thianthrene cation radical perchlorate in acetonitrile solvent. These reactions caused oxidative intramolecular cyclization, producing 1,3,4-oxadiazoles as the major product. During this investigation some interesting observations were made. Reactions were generally slow and the yield of the product oxadiazole was moderate. However, addition of a small amount of water to the reaction mixture dramatically accelerated the reaction and increased the yield of the oxadiazole. Therefore, it was of interest to explore the mechanistic aspects of these reactions further and to probe the possible role of added water in enhancing the reaction and product yield.
dc.format.mimetypeapplication/pdf
dc.identifier.urihttp://hdl.handle.net/2346/17785en_US
dc.language.isoeng
dc.publisherTexas Tech Universityen_US
dc.rights.availabilityUnrestricted.
dc.subjectHydrazonesen_US
dc.subjectRing formationen_US
dc.subjectRadicalsen_US
dc.subjectCationsen_US
dc.titleThianthrene cation radical induced reactions of semicarbazones and acylhydrazones
dc.typeDissertation
thesis.degree.departmentChemistry
thesis.degree.departmentChemistry and Biochemistry
thesis.degree.disciplineChemistry
thesis.degree.grantorTexas Tech University
thesis.degree.levelDoctoral
thesis.degree.namePh.D.

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