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Related Concept Videos

Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

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Related Experiment Video

Updated: May 21, 2026

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
07:07

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

A persistent (amino)(ferrocenyl)carbene().

Alan Dehope1, Daniel Mendoza-Espinosa, Bruno Donnadieu

  • 1UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California Riverside, Riverside, CA 92521-0403, USA.

New Journal of Chemistry = Nouveau Journal De Chimie
|June 19, 2012
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel (amino)(ferrocenyl)carbene, a reactive intermediate. This unstable organometallic compound was successfully isolated and characterized, offering new insights into ferrocene chemistry.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Published on: August 12, 2019

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Last Updated: May 21, 2026

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
07:07

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Published on: August 12, 2019

Area of Science:

  • Organometallic Chemistry
  • Carbene Chemistry
  • Ferrocene Derivatives

Background:

  • Ferrocene-containing carbenes are valuable synthetic intermediates.
  • Challenges exist in the synthesis and isolation of these reactive species.

Purpose of the Study:

  • To synthesize and characterize a novel (amino)(ferrocenyl)carbene.
  • To explore the reactivity and stability of this new carbene.

Main Methods:

  • Deprotonation of ferrocenylaldiminium salts.
  • Reaction of fulvenes with iron precursors.
  • Isolation via low-temperature deprotonation.
  • Characterization using NMR spectroscopy and X-ray diffraction.

Main Results:

  • Successful synthesis of a tetramethylferrocenylaldiminium salt and a nonamethylferrocenylaldiminium salt.
  • Isolation of the target (amino)(ferrocenyl)carbene as a yellow powder.
  • Demonstration of carbene instability (<48h at -20°C).
  • Characterization of a sulfur adduct confirming carbene nature.

Conclusions:

  • A new (amino)(ferrocenyl)carbene was synthesized and isolated.
  • The carbene exhibits limited stability, necessitating careful handling.
  • Sulfur trapping provides definitive evidence for carbene formation.