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Related Concept Videos

Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

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Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
1.9K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.1K
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.
10.1K
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

4.6K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
4.6K
Metallic Solids02:37

Metallic Solids

18.4K
Metallic solids such as crystals of copper, aluminum, and iron are formed by metal atoms. The structure of metallic crystals is often described as a uniform distribution of atomic nuclei within a “sea” of delocalized electrons. The atoms within such a metallic solid are held together by a unique force known as metallic bonding that gives rise to many useful and varied bulk properties.
All metallic solids exhibit high thermal and electrical conductivity, metallic luster, and malleability....
18.4K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

2.8K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
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Characterization of Electrode Materials for Lithium Ion and Sodium Ion Batteries Using Synchrotron Radiation Techniques
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A lithium-aluminium heterobimetallic dimetallocene.

Inga-Alexandra Bischoff1, Sergi Danés1, Philipp Thoni1

  • 1Department of Chemistry, Faculty of Natural Sciences and Technology, Saarland University, Saarbrücken, Germany.

Nature Chemistry
|May 14, 2024
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel heterobimetallic dimetallocene featuring a lithium-aluminum bond. This new compound, characterized by X-ray diffraction and NMR spectroscopy, exhibits an easily cleavable Al-Li bond, opening avenues for new organometallic chemistry.

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry

Background:

  • Homobimetallic dimetallocenes are rare, with limited examples like dizincocene and diberyllocene.
  • The synthesis of heterobimetallic analogues presents unique challenges and opportunities in inorganic chemistry.

Purpose of the Study:

  • To synthesize and structurally characterize a novel heterobimetallic dimetallocene containing lithium and aluminum.
  • To investigate the bonding characteristics and reactivity of the Al-Li bond within this new dimetallocene framework.

Main Methods:

  • Heterocoupling of lithium and aluminylene fragments with pentaisopropylcyclopentadienyl ligands.
  • Isolation and characterization of a cyclopentadienylaluminylene monomer.
  • Structural authentication via single-crystal X-ray diffraction.
  • Solution and solid-state characterization using multinuclear NMR spectroscopy.

Main Results:

  • Successful synthesis of a heterobimetallic dimetallocene with a high ionic character Al-Li bond.
  • Identification of significant dispersion interactions between isopropyl groups on the cyclopentadienyl ligands.
  • Isolation and characterization of a key cyclopentadienylaluminylene intermediate.
  • Demonstration of the Al-Li bond's susceptibility to cleavage upon reaction with N-heterocyclic carbenes and heteroallenes.

Conclusions:

  • The study reports the first synthesis and characterization of a lithium-aluminum heterobimetallic dimetallocene.
  • The Al-Li bond exhibits unique electronic and steric properties influenced by the bulky ligands.
  • The facile cleavage of the Al-Li bond suggests potential applications in synthetic transformations.