Related Experiment Video
Updated: Feb 22, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
Use of (Cyclopentadienone)iron Tricarbonyl Complexes for C-N Bond Formation Reactions between Amines and Alcohols
Thomas J Brown1, Madeleine Cumbes1, Louis J Diorazio2
1Department of Chemistry, The University of Warwick , Coventry CV4 7AL, U.K.
Abstract:
The application of a series of (cyclopentadienone)iron tricarbonyl complexes to "borrowing hydrogen" reactions between amines and alcohols was completed in order to assess their catalytic activity. The electronic variation of the aromatic groups flanking the C═O of the cyclopentadienone influenced the efficiency of the reactions; however, in other cases, the Knölker catalyst 1, containing trimethylsilyl groups flanking the cyclopentadienone ketone, gave the best results. In some cases, the change of the ratio of amine to alcohol improves the conversion significantly. The application of iron catalysts to the synthesis of a range of amines, including unsaturated amines, was investigated.
Related Concept Videos
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
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...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

