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Research On The Oxidation Of Olefins Catalyzed By The 12-tungstophosphoric Acid/hydrogen Peroxide System And The Design And Synthesis Of The N-heterocyclic Carbene Catalyst

Posted on:2007-11-17Degree:MasterType:Thesis
Country:ChinaCandidate:Y F ZhangFull Text:PDF
GTID:2121360185478049Subject:Organic Chemistry
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1. The Research in the Oxidation of Olefins Catalyzed by the 12-Tungstophosphoric Acid/Hydrogen Peroxide SystemA series of olefins were synthesized, and then oxidated by hydrogen peroxide in the inexpensive 12-tungstophosphoric acid / cetylpyridinium chloride system . The styrene was chosed as our working model to study the influences of the catalyst, phase-transfer catalyst, solvents and temperatures. The recovered catalyst at least can be recycled three times without significant loss of the activity. Various acyloins were obtained in good yields and high regioselectivies.2.The Design and Synthesis of the N-Heterocyclic Carbene CatalystThe N-heterocyclic carbene catalyst for the asymmetric benzoin reactions were designed and synthesized. Condensation of 2-naphthol and the bromo substituted benzaldehyde in the presence of ammonina gave Betti base in good yields. Then resolution of the Betti base with the D-(-)-tartaric acid in acetone gave the chiral Betti base in excellent yields. And then formation the cycle, at last treated with dimethyl sulfate, phenylhydrazine, trimethyl orthoformate to provide the chiral N-heterocyclic carbene catalyst.
Keywords/Search Tags:12-tungstophosphoric acid, metal / hydrogen peroxide system, olefin, oxidation, chiral N-hetercyclic carbene
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