Understanding Reactivity Patterns of the Dialkylaniline Radical Cation

N,N-Dimethylaniline and N,N-diethylaniline react with Cu2+ to form the corresponding amine radical cations. The radical cations were characterized by their absorption spectra. In the absence of any nucleophiles, the radical cations dimerize to give tetraalkylbenzidines, and this reaction can be moni...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-12, Vol.71 (26), p.9849-9852
Main Authors: Kirchgessner, Micha, Sreenath, Kesavapillai, Gopidas, Karical R
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Organic chemistry
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Summary:N,N-Dimethylaniline and N,N-diethylaniline react with Cu2+ to form the corresponding amine radical cations. The radical cations were characterized by their absorption spectra. In the absence of any nucleophiles, the radical cations dimerize to give tetraalkylbenzidines, and this reaction can be monitored by absorption spectroscopy. In the presence of nucleophiles such as Cl⊖, Br⊖, or SCN⊖, the radical cations undergo nucleophilic substitution to give para-substituted dialkylanilines in good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo061809i