A Study On γ-Butyrolactones Synthesis And Cyclization Of Aryl Compounds Using A Catalytic Amount Of Iodobenaene Via The In Situ Generated Organic Hypervalent Iodine Intermediates

The main studies of this dissertation are about application of catalytic amount of iodobenzene, which are transferred into hypervalent iodine intermediates, in the synthesis of γ-butyrolactones and chlorination of aromatic compounds with electron-donating groups. This thesis is divided into three chapters, the main contents as follows:1. Hypervalent iodine compounds have received a great deal of attention, due to their low toxicity, ready availability, easy handling and reactivity similar to that of heavy metal reagents or anodic oxidation. They have been extensively used as mild, highly selective and environmentally friendly reagents in organic reactions, such as oxidations, substitutions, additions, and rearrangement reactions, and the recent developments of them have been received in Chapter1.2. A metal-free method for the direct formation of y-butyrolactones has been developed. This reaction involves hypervalent iodine species generated in suit of from catalytic amount of PhI and mCPBA in the presence of KBr in CF3CH2OH (TFE). Under this condition, various carboxylic and benzoic acids affords corresponding y-lactones.3. An efficient method was developed for chlorination of aromatic compounds with electron-donating groups using iodobenzene as the catalyst and m-chloroperbenzoic acid as the terminal oxidant in the presence of4-methylbenzenesulfonic acid in THF, and a series of the monochlorinated compounds was obtained in good yields.