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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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Published on: July 27, 2022

A Dirhoda-Heterocyclic Carbene.

Harrison J Barnett¹, Anthony F Hill¹

¹Research School of Chemistry, The Australian National University, Canberra, ACT, 2601, Australia.

Angewandte Chemie (International Ed. in English)

|December 19, 2019

Summary

The rhodium carbide complex reacts with DMAD to form a novel dirhodium-heterocyclic carbene. This unique structure exhibits a bent RhCRh linkage and can coordinate with additional metal centers.

Keywords:

carbide complexes carbodicarbenes dirhoda-heterocyclic carbenes metalla-aromaticity

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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Published on: March 20, 2017

Area of Science:

Organometallic Chemistry
Coordination Chemistry
Carbene Chemistry

Background:

The study focuses on the reactivity of linear μ-carbido rhodium complexes.
Bis(diphenylphosphino)methane (dppm) is a common ligand in rhodium chemistry.

Purpose of the Study:

To investigate the reaction of a specific linear μ-carbido rhodium complex with dimethylacetylene dicarboxylate (DMAD).
To characterize the resulting product and explore its potential as a dirhodium-heterocyclic carbene.

Main Methods:

Synthesis of the linear μ-carbido complex [Rh2(μ-C)Cl2(dppm)2].
Reaction of the complex with DMAD.
Structural characterization of the product, likely involving X-ray crystallography.

Main Results:

The reaction yields a new complex, [Rh2(μ-C)(μ-DMAD)Cl2(dppm)2].
This complex features a bent RhCRh linkage with a bond angle of 124.7°.
The structure suggests the carbido ligand can act as a dirhodium-heterocyclic carbene.

Conclusions:

The reaction of [Rh2(μ-C)Cl2(dppm)2] with DMAD forms a stable dirhodium-heterocyclic carbene complex.
The bent RhCRh core is a key feature, enabling further coordination.
This finding expands the understanding of carbido ligand reactivity in organometallic chemistry.