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Synlett 2009(14): 2305-2308  
DOI: 10.1055/s-0029-1217813
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Unexpected Reactions of Push-Pull N-Heterocyclic Carbene Derived from N-(4-Methoxyphenyl)-N-(4-nitrophenyl)-imidazolium Chloride

Zhi-Qiang Zhua, Ming-Yue Jiangb, Jin-Hong Lina, Cheng-Pan Zhanga, Xiao-Chun Hanga, Chang-Ge Zhengb, Qing-Yun Chena, Ji-Chang Xiao*a
a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: jchxiao@mail.sioc.ac.cn;
b School of Chemical and Material Engineering, Southern Yantze University, 1800 Lihu Road, Wuxi 214122, P. R. of China
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Publication History

Received 5 May 2009
Publication Date:
07 August 2009 (online)

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Abstract

A new precursor of N-heterocyclic carbene bearing push-pull substituents has been synthesized by the quaternization of 1-(4-methoxyphenyl)-imidazole. Unexpected reactions between the carbene generated in situ and aromatic aldehydes or acrylates were observed resulting in the formation of imidazole derivatives.

Key words

N-heterocyclic carbenes - nucleophilic addition - aromatic substitution - rearrangements

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CCDC 690599 and CCDC 690600 contain the supplementary crystallographic data for compounds 2a and 3a. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.