An n-heterocyclic-carbene-tetracyanoethylene zwitterion: Experimental and theoretical study on its formation and reactivity

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Title
An n-heterocyclic-carbene-tetracyanoethylene zwitterion: Experimental and theoretical study on its formation and reactivity
Author(s)
Hayoung Song; Youngsuk Kim; Junbeom Park.; Ko Y.H.; Kim K.; Lee E.
Publication Date
2017-03
Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v.2017, no.8, pp.1231 - 1235
Publisher
WILEY-V C H VERLAG GMBH
Abstract
The direct addition of tetracyanoethylene (TCNto the carbene center of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPwas 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. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/4812
ISSN
1434-193X
Appears in Collections:
Center for Self-assembly and Complexity(복잡계 자기조립 연구단) > Journal Papers (저널논문)
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