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Acidic Ionic Liquid-Catalyzed Addition Reaction and Cascade Reaction

Author: GuoHui
Tutor: LinXianFu
School: Zhejiang University
Course: Chemistry
Keywords: Acidic ionic liquid oxa-Michael addition O- addition C- addition Tetrahydroquinoline compound
CLC: O643.32
Type: PhD thesis
Year: 2011
Downloads: 74
Quote: 0
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Abstract


As people's awareness of environmental protection, green chemistry has become a hot research. Acidic ionic liquid because of its own unique physical and chemical properties has been widely used in recent years to become an important way of green chemistry. Lewis acidic ionic liquid BY BRONSTED acidic ionic liquids and immobilized acidic ionic liquid preparation as well as the important results achieved in the green synthesis has greatly expanded the application of acidic ionic liquids in the field of Chemistry and Chemical Engineering. The paper found a new activity of acidic ionic liquid at room temperature and efficient catalytic oxa-Michael addition reaction, the study found that acidic ionic liquid capable of catalyzing alcohol oxa-Michael addition reaction between benzyl amino alcohol compounds butenone, acrolein . Investigated and negative ions of the ionic liquid, the amount of ionic liquid, and the reaction temperature, substrate ratio, reaction time, and substrate structure of the oxa-Michael addition reaction. The experimental results show that, compared with the results of the traditional organic acids and imidazoles acidic ionic liquid catalyzed designed amides prepared acidic ionic liquid has a better catalytic performance. Lactam acidic ionic liquid catalyzed oxa-Michael addition reaction mechanism is proposed and validated through experiments the mechanism. The paper studies the reaction catalyzed by acidic ionic liquid phenolic compounds selective addition of new features. The addition reaction between the phenolic compound of the acidic ionic liquid catalyst butenone, acrolein and acrylonitrile, examines the type of ionic liquid, the amount of ionic liquid, and the reaction temperature, the proportion of substrate, reaction time and Substituents on The addition of the impact of the reaction. Neutral ionic liquid and an acidic ionic liquid catalyzed difference found, controllable selective addition reaction can occur in the acidic ionic liquid, a phenolic compound; neutral ionic liquid, phenolic compound can not happen controllable selective addition reaction. Experimental results show that the nature and location of the substituent has an important influence on the phenolic compound of the chemical addition reaction occurs and regioselectivity. On the basis of the experiments, a possible mechanism for the addition reaction catalyzed by acidic ionic liquid phenolic compounds selectively. The thesis explores new ways of acidic ionic liquid catalytic tandem reaction synthesis of tetrahydroquinoline compounds. Tandem reaction between the alcohol compound of the acidic ionic liquid catalyst phenylamino butenone, ethyl vinyl ketone, and the effects of the ionic liquid type, the amount of ionic liquid, and the reaction temperature, substrate ratio, reaction time, the bottom physical structure, the influence of the organic solvent on the reaction of compounds of the synthetic tetrahydroquinoline. The experimental results show that the two-phase system consisting of acidic ionic liquid and trichloromethane having better catalytic effect. Under this condition, a series of the novel structure of the tetrahydroquinoline compound is synthesized. Acidic ionic liquid catalytic synthesis of tetrahydroquinoline compounds tandem reaction process, and verified by the experiment of the course. Papers Total Synthesis of the 64 kinds of compounds, of which 13, 18 kinds of the ionic liquid oxa-Michael addition product, nine kinds of C-addition product, the 7-O-addition product, the eight kinds of phenyl amino alcohol compound, 6 FOUR hydrogen quinoline compounds and N-into a product, the product through means of 1H NMR, 13C NMR, FTIR, HRMS characterization analysis and validation, 30 of which are new compounds.

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Chemical kinetics,catalysis > Catalytic > Catalytic reaction
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