Applications Of Hypervalent Iodine Compound IBX And TBAB In Organic Synthesis

This thesis descries two new applications of the combination of hypervalentiodine compound2-iodoxybenzoic (IBX) with tetraethyl ammonium bromide (TBAB)in organic synthesis.One is the application of IBX in the decarboxylative bromination of cinnamicacidsVinyl bromides are important synthetic intermediates in organic synthesis, theywere obtained easily by decarboxylative bromination of α, β-unsaturated carboxylicacids. In this thesis the decarboxylative bromination of cinnamic acids was exploredusing IBX as the oxidant with TBAB as the brominating agents to giveβ-bromostyrenes, further investigations showed other vinyl halides can be alsoaccessed by their corresponding quaternary ammonium salts or metal halides as thehalogenation reagents.Another is the synthesis of2-iodobenzoate esters by reaction of IBX withhalogenated hydrocarbon (RX)2-Iodobenzoate esters were gotten easily and efficiently from IBX with RX inthe presence of TBAB. Most importantly, mono-or bi-substitution products ofdihalides can be controlled by the ration of the reactants. And the bi-(2-iodobenzoateesters) were furtherly oxidized and the single-crystal X-ray analysis of compound32reveals a pseudo benziodoxole structure with strong intramolecular I…O interactions.