An N-Heterocyclic-Carbene–Tetracyanoethylene Zwitterion: Experimental and Theoretical Study on Its Formation and Reactivity
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SCOPUS
- Title
- An N-Heterocyclic-Carbene–Tetracyanoethylene Zwitterion: Experimental and Theoretical Study on Its Formation and Reactivity
- Authors
- HAYOUNG, SONG; YOUNGSUK, KIM; JUNBEOM, PARK; KO, YOUNG HO; KIM, KIMOON; LEE, EUNSUNG
- Date Issued
- 2017-02-24
- Publisher
- WILEY-V C H VERLAG GMBH
- Abstract
- The direct addition of tetracyanoethylene (TCNE) to the carbene center of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) was successfully demonstrated. The IPr–TCNE adduct, that is, zwitterion 1, clearly differs from the typical [2+1]-cycloaddition products obtained from the reaction of carbenes with olefins. The results obtained from experimental and theoretical studies suggest that adduct 1 disassembles into IPr and TCNE, which is followed by the addition of IPr to the nitrile carbon atom of TCNE and subsequent isomerization into a thermodynamically more stable singlet nitrene intermediate. This intermediate is then captured by an additional molecule of TCNE to afford another heterocycle. This study reveals a unique example of the reactivity between N-heterocyclic carbenes and olefins.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/40979
- DOI
- 10.1002/ejoc.201601648
- ISSN
- 1434-193X
- Article Type
- Article
- Citation
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 8, no. 8, page. 1231 - 1235, 2017-02-24
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