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Ding WJ, Fang DC. Theoretical studies on cycloaddition reactions between keteniminium cations and olefins. J Org Chem. 2001;66(20):6673-8doi: 10.1021/jo010461i.
Ding, W. J., & Fang, D. C. (2001). Theoretical studies on cycloaddition reactions between keteniminium cations and olefins. The Journal of organic chemistry, 66(20), 6673-8. https://doi.org/10.1021/jo010461i
Ding, W J, and Fang, D C. "Theoretical studies on cycloaddition reactions between keteniminium cations and olefins." The Journal of organic chemistry vol. 66,20 (2001): 6673-8. doi: https://doi.org/10.1021/jo010461i
Ding WJ, Fang DC. Theoretical studies on cycloaddition reactions between keteniminium cations and olefins. J Org Chem. 2001 Oct 05;66(20):6673-8. doi: 10.1021/jo010461i. PMID: 11578220.
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J Org Chem. 2001 Oct 05;66(20):6673-8. doi: 10.1021/jo010461i.

Theoretical studies on cycloaddition reactions between keteniminium cations and olefins.

The Journal of organic chemistry

W J Ding, D C Fang

Affiliations

  1. Department of Chemistry, Beijing Normal University, 100875, People's Republic of China.

PMID: 11578220 DOI: 10.1021/jo010461i

Abstract

The mechanisms of seven reactions between keteniminium cations and olefins have been theoretically explored at BHandHLYP/6-31G level. It is found that these seven reactions always form a relatively stable hydrogen-bonded type of ion-molecule complex first except for reactions 1d+2a and 1e+2a, which have no hydrogen atom attached to nitrogen atom in keteniminium cations. Some reactions take place via a concerted but unsynchronous mechanism, and the others are stepwise processes. The substituent effects are also studied. The data reveal that the electron-pushing substituents on keteniminium cations disfavor the reaction, and the electron-attracting substituents on keteniminium cations favor the reactions. The substituent effects on ethene are contrary to the former case.

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