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Study On The Benzylic Oxidation Utilizing A Catalytic Amount Of Hypervalent Of Iodine Reagent

Posted on:2014-06-14Degree:MasterType:Thesis
Country:ChinaCandidate:Y XuFull Text:PDF
GTID:2251330401482560Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
This paper is divided into two chapters. The first one introduces the history of hypervalent iodine compounds and as a green reagent, compared to metal oxidants, such as Mercury salt Hg (Ⅱ), Thallium salt T1(Ⅲ) and lead salt Pb (Ⅳ), hypervalent iodine compounds own the similar chemical properties and reactivities but have the advantages of mild reaction condition, high selectivity and environmental harmless etc. Secondly, I made a classification of various trivalent iodine reagents which I payed attention to and summarization of their latest application, especially the diacarboxyiodobenzene (PIDA/PIFA) involved in the experiments of this thesis which I consulted to a abundant of references. The application of solid-supported diacarboxyiodobenzene cooperated with ionic liquids in organic synthesis not only overcomes the shortcomings of two-phases reaction but also prolongs the life of the hypervalent iodine reagent. Finally, I carried out the approach of utilizing a catalytic amount of hypervalent iodine reagent in my research.The second chapter is divided into two parts, on the part one, I analyzed the situation of benzyl C-H activated oxidation. Making use of a catalytic amount of transition metal to oxidize substrates to generate the corresponding aromatic ketones is one of main methods at present. Putting hypervalent iodine reagents into use to realize transformation not only can achieve the desired results, but also cater to the requirements of green chemistry. The experiment part, I utilized two methods with a catalytic amount of diacetoxyiodobenzene to achieve the oxidation of benzyl compounds. By screening different temperature, solvent, ratio of substrates and time duration, I obtained the optimum condition on which I extended the substrates and received good to excellent yields. Then I made a reasonable inference of the reaction mechanism. Melting point of products, copies of original1H and13C NMR spectra are listed at the end of the thesis.
Keywords/Search Tags:Hypervalent Iodine Reagent, Diacetoxyiodobenzene, Aromatic Ketone, Catalytic Oxidation, Transition Metal
PDF Full Text Request
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