Shea, Michael2019-12-112019-12-112019-08https://hdl.handle.net/11299/208961University of Minnesota M.S. thesis. August 2019. Major: Chemistry. Advisor: Viktor Zhdankin. 1 computer file (PDF); x, 125 pages.Nitrogen containing mono-heterocyclic hypervalent iodine(III) compounds, benziodazoles, have been investigated by several research groups as well as ours. These compounds are commonly used as efficient oxidative reagents for various organic substrates. The preparation, structure, and reactivity of the first bicyclic benziodazole compound, N,N’-diisopropylbenziodazole, will be reported and compared to the monocyclic N-isopropyl-m-chlorobenzoate benziodazole. Both benziodazoles were prepared by the m-chloroperoxybenzoic acid oxidation of 2-iodo-N-isopropylbenzamide or 2-iodo-N,N'-diisiopropylisophthalamide, respectively, and their structures were established by X-ray crystallography. These benziodazoles were investigated as efficient reagents for oxidatively assisted coupling reactions to form esters and amides.enAmideBenziodazoleEsterHypervalentIodineThesis or Dissertation