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- W2324496670 abstract "The first theoretical investigation using density functional theory (DFT) methods to study the detailed reaction mechanisms of stereoselective [2 + 2 + 2] multimolecular cycloaddition of ketene (two molecules) and carbon disulfide (CS2, one molecule) which is catalyzed by N-heterocyclic carbene (NHC) is presented in this paper. The calculated results indicate that this reaction occurs through four steps: the complexation of NHC with ketene (channel 1a) rather than with CS2 (channel 1b), addition of CS2 (channel 2b) but not dimerization of ketene (channel 2a), formal [4 + 2] cycloaddition with a second molecule of ketene (channel 3a) rather than intramolecular [2 + 2] cycloaddition (channel 3b), and finally regeneration of NHC. The second step is revealed to be the rate-determining step. Moreover, the stereoselectivities associated with the chiral carbon center and the carbon double bond are predicted to be respectively determined in the second and third steps and respectively R and E configurations dominated, which are in good agreement with the experimental results. Furthermore, the possible mechanisms of the identical [2 + 2 + 2] cycloaddition catalyzed by N,N-dimethylpyridin-4-amine (DMAP) have also been investigated to help understand the ring closure mechanism proceeding in the third step." @default.
- W2324496670 created "2016-06-24" @default.
- W2324496670 creator A5013574828 @default.
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- W2324496670 date "2013-11-20" @default.
- W2324496670 modified "2023-09-27" @default.
- W2324496670 title "DFT Investigation on Mechanisms and Stereoselectivities of [2 + 2 + 2] Multimolecular Cycloaddition of Ketenes and Carbon Disulfide Catalyzed by N-Heterocyclic Carbenes" @default.
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- W2324496670 doi "https://doi.org/10.1021/jo4018809" @default.
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