Reaction Mechanism of CO2 and Styrene Oxide Catalyzed by Ionic Liquids: A Combined DFT Calculation and Experimental
Jinyin Zha1, Tong Ding2, Jian Chen1
1School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
Abstract:
Bioactive compound 3-aryl-2-oxazolidinone could be synthesized by a green method mixing carbon dioxide, aniline, and ethylene oxide. Our group previously proposed a parallel mechanism for this conversion catalyzed by ionic liquids. Recently, a new study on a similar reaction system of styrene oxide, carbon dioxide, and aniline under the catalysis of K3PO4 gave a different serial mechanism. In order to explore the mechanism of reaction, we conducted a combined theoretical and experimental study on a one-pot conversion of styrene oxide, carbon dioxide, and aniline. In experiments, two isomer products, 3,5-diphenyl-l,3-oxazolidin-2-one and 3,4-diphenyl-l,3-oxazolidin-2-one, were observed. The computational results show that the parallel mechanism is more favored in thermodynamics and in kinetics due to the instability of isocyanate and hardness of its generation. Hence, we believe the previous parallel mechanism is more reasonable under our catalysts and conditions.
More Related Videos
Related Concept Videos
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
E2 Reaction: Kinetics and Mechanism
Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control
Catalysis
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Radical Reactivity: Steric Effects
Along with electronic...


