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Studies on the Carbon-carbon Coupling Reactions of α-Oxoketene Dithioacetals in the Conditions of Catalyst

Author: JiangYaZuo
Tutor: LiuZaiQun；WangShuGang
School: Jilin University
Course: Organic Chemistry
Keywords: alpha - carbonyl ketene Michael addition [ 5C 1C ] cyclization Cu ( II ) - catalyzed C-C coupling
CLC: O621.25
Type: Master's thesis
Year: 2011
Downloads: 59
Quote: 0
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Abstract


Since 1910 alpha - benzoyl dimethyl sulfide ketene was first kelber to synthetic alpha - carbonyl ketene more and more people's attention. alpha - carbonyl ketene is an important intermediate for organic synthesis , it has easy to prepare , carry characteristic functional groups , etc. . alpha - carbonyl ketene chemistry research in the past 30 years has gradually taken shape , and synthetic organic chemistry position occupied more and more important . In addition, the carbon-carbon bond formation under catalytic conditions Another important reaction in synthetic organic chemistry , especially carbon-carbon bond coupling cyclization reaction has been widespread concern . We found in the the ketene study of alpha - carbonyl disulfide , alkylthio , due to space electronic effects of alpha - carbonyl disulfide reduction of the chemical behavior of the enone compounds has a regulatory role , this role in carbon important carbon bond formation . In this thesis, the alpha - carbonyl disulfide ketene synthesis work is based on the development of new primitives synthesis reaction and explore new synthetic method for the target , focused on the alpha - carbonyl ketene and carbon negative ions in the Cu catalyst under the coupling reaction , the synthesis of a series of multi- substituted aromatic ring compound , further development [ 5C 1C ] to form a ring strategy . The specific studies were as follows: 1. Using the existing literature methods to the synthesis of a series of alpha - carbonyl disulfide ketene substrate . 2 under the action of an alkali and o, respectively , the reaction of p-hydroxybenzaldehyde , the formation position of the type having a hydroxyl group of large conjugated system , and thus to test the biological activity of the system . 3 under acidic conditions to restore the alpha - carbonyl ketene C = C double bond is carried out under catalysis with a compound containing active methylene the [ 5C 1C ] ring-forming reaction , synthesis of 9 multi- substituted aromatic compound .

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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