Studies On The Application Of IBX In Organic Synthesis

This thesis describes the addition of ketones and the substitution of alkenes with hypervalent iodine compound orthoiodoxybenzoic acid (IBX). It is divided into threemajor parts as follows:1. Recent Progress of Hypervalent Iodine Compounds in Organic Synthesis The review summarizes the history of hypervalent iodine chemistry and focusesmainly on the common members of the hypervalent iodine compound family. The recent progress of them in organic synthetic reactions such as oxidation, addition, substitution and rearrangement was provided by references, which all are newly published in leading international journals.2. Substitution of Ketones with IBXAlthough hypervalent iodine has been used as an oxidant in substitution reactions, we have explored the synthesis and structure of bi-substituted and mono-substituted α-(2-iodophenylcarboxyl)ketones from IBX and ketones, which is the first entry of IBX as starting material. In this reaction, the products contain the main skeleton structure of IBX presenting highly atom economy. All of the new compounds were characterized by not only NMR, MS and IR spectra, but also the single-crystal X-ray analysis in the case of the product 3e.3. Addition of Alkenes with IBXOn continuing our studies on the chemistry of hypervalent iodines, we found that an addition of IBX to alkenes, which can be conveniently halo-oxygenation of alkenes in one step. The reaction presented not only regio-selectivity, but also stereoselectivity for cycloalkenes.