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Applications Of Inorganic Mono-electron Oxidants In Organic Reaction

Posted on:2009-05-24Degree:DoctorType:Dissertation
Country:ChinaCandidate:G L WuFull Text:PDF
GTID:1101360245481556Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
The thesis mainly focused on the application of inorganic mono-electron oxidants in organic reaction. The inorganic mono-electron oxidants used here Oxone? (KHSO5·KHSO4·K2SO4) and Nitrosonium (NO+). This paper is divided into six parts as follows:Chapter 1 opens with a review on the previous studies of Oxone?. It will be involved in development of Oxone? chemistry and various organic reactions, in which Oxone? participates.Chapter 2 provides thiocyanations of aromatic and heteroaromatic compounds using Oxone? as an oxidant. These reactions exhibited a good regioselectivity and The reactivity thiocyanate group will be readily transformed into other sulfur-bearing functionalities. All these products are particularly useful for producing drugs and Pharmaceuticals.Chapter 3 develops the Oxone-mediated thiocyanation on 1, 1-disubstituted olefins in methanol. It afforded 1-methoxyl-2-thiocyano adducts in a yield of 70%, being very useful in organic synthesis.Chapter 4 shows the Oxone-mediated oxidative 3-arylthio substitution of indoles. The formed products could serve as selective cyclooxygenase-2 (COX-2) inhibitors.Chapter 5 extends on the study to nitrosonium (NO+), NO+ was found to catalyse the Michael addition of oximes onto N-vinyl-2-pyrrolidinone. Thiols here used to react with N-vinyl-2-pyrrolidinone, Some thio ether compounds were formed in a good yield. It is an easy way to build C-X (O,S) bounds. In chapter 6, Nitrosonium (NO+ ) has applied to catalyze Michael addition of indoles to unsaturated enones. The reaction uniquely occurred at the 3-position of indole ring. It offers a good way to prepare indole derivatives.In conclusion, This is a effect toward the green chemistry. In general, these reactions offer several advantages with commercially available reagents, with reaction condition easy handling and good yields.
Keywords/Search Tags:Mono-electron
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