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Several Types Of Hypervalent Iodine Reagents In Organic Synthesis Applications

Posted on:2009-03-18Degree:MasterType:Thesis
Country:ChinaCandidate:L Z ChaiFull Text:PDF
GTID:2191360272957708Subject:Organic Chemistry
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The application of inorganic hypervalent iodines compounds is are the topic of this dissertatio- n.We have developed a series of novel systems using inorganic hypervalent iodines reagents such as iodic acid(HIO3), iodine pentoxide (I2O5) as the stoichiometric oxidants and halogenated reagents.As the extention of our studies on the application of inorganic hypervalent iodines, aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines with HIO3 and I2O5 in water which demonstrated a novel and mild method has been firstly reported.Meanwhile, the successful hydroxyhalogenation of double C-C bond suggests futher the high efficient,atom economic,wild, convenient and environmental benign feature of those novel oxidation systems.The thesis is divided into four chapters as follows:In the chapter 1:The review summarizes the progress of the chemistry of hypervalent iodine and focuses mainly on the common members of the hypervalent iodine compounds which includes the preparations, chemical actions and utilizations in organic synthesis.In the chapter 2: Many of the processes of oxidative aromatization of five- or six - membered heterocyclic compounds involved expensive transition metal oxidants, relatively overloading of organic solvents. In order to solve this problem from atom economic view, we have firstly reported the smoothly aromatization of Hantzsch 1,4-dihydropyridines(1,4-DHPs) by using catalystic amount of HIO3 or I2O5 as the stoichiometric oxidation reagent in water which provided a novel,mild, efficient method.In the chapter 3: We have explored the reaction of oxidation of 1,3,5-trisubstituted pyrazolines using I2O5 as oxidant at the presence of KBr. It has proved to be a green and enironmental friendly novel oxidation system.In the chapter 4: We have studied the hydroxyhalogenation of C-C double bond utilizing I2O5 and KBr in the presence of initiating agent H2O2 or not.
Keywords/Search Tags:Hypervalent iodine, Oxidation, Aromatization, Hydroxyhalogenation, Atom-efficiency, Green synthesis
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