Related Experiment Video
Updated: Jun 25, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Superelectrophilic chemistry of imidazoles
Matthew R Sheets1, Ang Li, Edward A Bower
1Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
Abstract:
The mechanistic and synthetic chemistry of imidazole-based superelectrophiles has been studied. The protonated imidazole ring, or imidazolium group, is shown to enhance the electrophilic reactivity of an adjacent carboxonium group (compared to a related monocationic species). This leads to efficient condensation reactions between imidazole aldehydes and ketone with arenes in the Brønsted superacid CF3SO3H. The imidazole-based superelectrophiles are shown to be useful in other reactions leading to functionalized heterocycles. The imidazolium group may also trigger charge migration reactions in dicationic species.
Related Concept Videos
Basicity of Heterocyclic Aromatic Amines
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophiles
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

