Related Experiment Video
Updated: Aug 4, 2026

14:07
Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Non-metathetic behavior patterns of Grubbs' carbene
Benito Alcaide1, Pedro Almendros
1Departamento de Química Orgánica, Facultad de Química. Universidad Complutense de Madrid, 28040 Madrid, Spain. alcaideb@quim.ucm.es
Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 20, 2003
Summary
Grubbs
Area of Science:
- Organometallic Chemistry
- Catalysis
- Organic Synthesis
Background:
- Grubbs' carbene complexes are highly efficient catalysts for olefin metathesis.
- These ruthenium-based catalysts are stable and tolerate various functional groups.
- Their synthetic utility extends beyond traditional olefin metathesis.
Purpose of the Study:
- To present recent advances in the non-metathetic applications of Grubbs' carbene complexes.
- To highlight the expanding synthetic utility of these ruthenium catalysts.
- To showcase novel catalytic processes mediated by Grubbs' carbene.
Main Methods:
- Review of recent literature on Grubbs' carbene complexes.
- Analysis of catalytic processes beyond olefin metathesis.
- Discussion of the properties enabling broad synthetic utility.
Main Results:
- Grubbs' carbene complexes exhibit significant efficiency in olefin metathesis.
- New catalytic processes mediated by these complexes have been discovered.
- The catalysts' stability and functional group tolerance are key to their versatility.
Conclusions:
- Grubbs' carbene complexes are valuable tools with applications beyond olefin metathesis.
- Recent advances reveal broader synthetic utility and novel catalytic behaviors.
- The versatility of these ruthenium catalysts makes them indispensable in modern organic synthesis.
Related Concept Videos
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...
Alcohols from Carbonyl Compounds: Grignard Reaction
Grignard reagents are one of the most commonly used reagents used to synthesize alcohols from carbonyl compounds. Grignard reagents are organomagnesium halides with a highly polar carbon–magnesium bond. Due to the partial ionic nature of the C–Mg bond, the carbon functions as a strong nucleophile and attacks electrophiles like carbonyl carbon.
Magnesium from the reagent coordinates with carbonyl oxygen, further reducing the carbonyl carbon's electron density. Thus, the carbonyl carbon is a...
Magnesium from the reagent coordinates with carbonyl oxygen, further reducing the carbonyl carbon's electron density. Thus, the carbonyl carbon is a...
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.
Nitriles to Ketones: Grignard Reaction
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard reagent...
The mechanism begins with a nucleophilic attack by the Grignard reagent...
Nucleophilic Aromatic Substitution: Elimination–Addition
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Radicals: Electronic Structure and Geometry
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...

