A Study On Organic Synthesis With Catalytic Amount Of Inorganic Iodide Via Organic Hypervalent Iodine Intermediates

The application of inorganic iodines in organic synthesis via organic hypervalent iodine intermediates is the topic of this dissertation. We had developed a new catalytic system using inorganic iodines such as ammonium iodide. As the extention of our studies on the application of inorganic iodines, a-tosyloxylation of ketones using catalyatic ammonium iodide and sulfonyloxylactonization of alkenoic acid under the catalysis of ammonium iodide which demonstrated a novel and mild method had been firstly reported. Meanwhile, the successful iodolactonization of alkenoic acid suggested the high efficient, atom economic, wild, convenient and environmental benign feature of those novel catalyatic systems. The thesis is divided into five chapters:1. We summarized the progress of inorganic iodines and focused mainly on the common members of the inorganic iodines which included the preparations and utilizations in organic synthesis.2. In order to solve some problems from atom economic view, we had developed a novel procedure for preparation of various a-tosyloxyketones in good yields by the reaction of ketones in the presence of catalytic amounts of ammonium iodide in a mixture of acetonitrile and2,2,2-trifluoroethanol(8:2). Additionally, some details about the mechanism were studied and a tentative mechanism had been proposed.3. We had explored a novel one-pot method for sulfonyloxylactonization of alkenoic acid using a catalytic amount of ammonium iodide and studied the iodolactonization of alkenoic acid in the presence of catalytic amounts of ammonium iodide. It had been proved to be a green and enironmental-friendly oxidation system.