Hypervalent Iodine Reagents for Tosyl Transfer Reactions in Organic Synthesis

University of Minnesota M.S. thesis. July 2015. Major: Chemistry. Advisors: Viktor Zhdankin, Akira Yoshimura. 1 computer file (PDF); xi, 114 pages.In recent years, organohypervalent iodine compounds have emerged as environmentally friendly and efficient reagents for various synthetically useful oxidative transformations. The purpose of this research is to take a closer look at newer five membered heterocyclic hypervalent iodine compounds similar to the hydroxy(tosyloxy)iodobenzene (HTIB) studied by G.F. Koser in the 1980's, which utilized different variations of iodobenzene with different functional groups in the para-position of a benzene ring in order to perform ligand transfer reactions. Utilizing Koser's framework new heterocyclic hypervalent iodine reagents have been synthesized using 2-iodobenzoic acid as well as other similar substrates as a starting material along with HTIB. Different variations of these heterocycles have been synthesized in order to analyze the structural and kinetic nature of these less studied derivatives and their overall reactivity for selective oxidations and tosyl-transfer reactions in organic synthesis