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Related Concept Videos

Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

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...
Elimination Reactions02:25

Elimination Reactions

A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called β elimination or...
Radical Formation: Elimination00:51

Radical Formation: Elimination

Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids01:24

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H] allows...

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Facile Preparation of Ultrafine Aluminum Hydroxide Particles with or without Mesoporous MCM-41 in Ambient Environments
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Facile Preparation of Ultrafine Aluminum Hydroxide Particles with or without Mesoporous MCM-41 in Ambient Environments

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Reductive elimination: a pathway to low-valent aluminium species.

Chelladurai Ganesamoorthy1, Sinah Loerke, Christian Gemel

  • 1Inorganic Chemistry II, Ruhr-University Bochum, Universitätsstrasse 150, 44801 Bochum, Germany.

Chemical Communications (Cambridge, England)
|February 6, 2013
PubMed
Summary

Organoaluminum compounds Cp*AlH2 and Cp*2AlH undergo reductive elimination of Cp*H under reflux. This reaction yields elemental aluminum (Al) and aluminum cyclopentadienyl (AlCp*) species, respectively.

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Facile Preparation of Ultrafine Aluminum Hydroxide Particles with or without Mesoporous MCM-41 in Ambient Environments
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Area of Science:

  • Organometallic Chemistry
  • Aluminum Chemistry
  • Reductive Elimination Reactions

Background:

  • Organoaluminum compounds are versatile reagents in synthesis and materials science.
  • Understanding their decomposition pathways is crucial for controlling reactivity and product formation.
  • Cp* (pentamethylcyclopentadienyl) ligands are commonly used to stabilize reactive metal centers.

Purpose of the Study:

  • To investigate the thermal decomposition of Cp*AlH2 and Cp*2AlH.
  • To determine the products formed from reductive elimination of Cp*H.
  • To explore the behavior of these aluminum compounds in aromatic solvents.

Main Methods:

  • Synthesis and characterization of Cp*AlH2 and Cp*2AlH.
  • Refluxing Cp*AlH2 and Cp*2AlH in benzene or toluene.
  • Analysis of reaction products using spectroscopic and analytical techniques.

Main Results:

  • Cp*AlH2 reductively eliminates Cp*H upon heating in benzene or toluene, yielding elemental aluminum (Al).
  • Cp*2AlH undergoes similar reductive elimination of Cp*H, producing aluminum cyclopentadienyl (AlCp*).
  • The solvent (benzene or toluene) does not significantly alter the decomposition products.

Conclusions:

  • Cp*AlH2 and Cp*2AlH are susceptible to reductive elimination of Cp*H under thermal stress.
  • These reactions provide a route to generating elemental aluminum and AlCp* species.
  • The findings contribute to the understanding of organoaluminum stability and reactivity.