Related Experiment Video
Updated: Sep 23, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
Acid-promoted olefination of ketones by an iron(III) porphyrin complex
Ying Chen1, Lingyu Huang, X Peter Zhang
1Department of Chemistry, University of Tennessee, Knoxville, Tennessee 37996-1600, USA.
Abstract:
[reaction: see text] The acid-promoted olefination of unactivated ketones with diazo reagents in the presence of triphenylphosphine can be catalyzed by the commercially available iron(III) porphyrin complex Fe(TPP)Cl. The reactions were effectively carried out under mild conditions in a one-pot fashion with the use of a stoichiometric diazo reagents and substoichiometric benzoic acid. Examples include aromatic, aliphatic, cyclic, and unsaturated ketones with ethyl diazoacetate or tert-butyl diazoacetate.
Related Concept Videos
α-Alkylation of Ketones via Enolate Ions
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is activated by...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

