Related Experiment Video
Updated: May 18, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Hybrid super electron donors - preparation and reactivity
Jean Garnier1, Douglas W Thomson, Shengze Zhou
1WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
Abstract:
Neutral organic electron donors, featuring pyridinylidene-imidazolylidene, pyridinylidene-benzimidazolylidene and imidazolylidene-benzimidazolylidene linkages are reported. The pyridinylidene-benzimidazolylidene and imidazolylidene-benzimidazolylidene hybrid systems were designed to be the first super electron donors to convert iodoarenes to aryl radicals at room temperature, and indeed both show evidence for significant aryl radical formation at room temperature. The stronger pyridinylidene-imidazolylidene donor converts iodoarenes to aryl anions efficiently under appropriate conditions (3 equiv of donor). The presence of excess sodium hydride base has a very important and selective effect on some of these electron-transfer reactions, and a rationale for this is proposed.
Related Concept Videos
Diels–Alder Reaction: Characteristics of Dienophiles
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends on...
Electrophiles
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
ortho–para-Directing Deactivators: Halogens
Redox Reactions
Redox Reactions

