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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...
4.2K
Metal-Ligand Bonds02:51

Metal-Ligand Bonds

25.3K
The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
25.3K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

4.3K
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...
4.3K
Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

3.3K
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
3.3K
Elimination Reactions02:25

Elimination Reactions

18.1K
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...
18.1K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.9K
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...
4.9K

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Ligand coordination modulates reductive elimination from aluminium(iii).

Stephanie J Urwin1, David M Rogers, Gary S Nichol

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, UK. michael.cowley@ed.ac.uk.

Dalton Transactions (Cambridge, England : 2003)
|August 18, 2016
PubMed
Summary

Reductive elimination from aluminum(III) centers is rare, but this study reveals ligand effects influencing this key reaction. Lewis bases inhibit reductive elimination, impacting main-group chemistry.

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Area of Science:

  • Organometallic Chemistry
  • Main-Group Chemistry
  • Reaction Mechanisms

Background:

  • Low-valent main-group elements are increasingly recognized for their ability to undergo oxidative addition of inert bonds.
  • Reductive elimination, the reverse reaction, is less common but crucial for catalytic cycles.
  • Understanding these reactions is vital for developing new synthetic methodologies.

Purpose of the Study:

  • To investigate the mechanism of reductive elimination from aluminum(III) centers.
  • To elucidate the role of ligands in controlling this process.
  • To provide experimental data on activation and thermodynamic parameters.

Main Methods:

  • Mechanistic study of reductive elimination from Cp*2AlH.
  • Experimental determination of activation parameters.
  • Thermodynamic analysis of the reaction.
  • Investigation of Lewis base inhibition.

Main Results:

  • Reductive elimination of Cp*H from Cp*2AlH was studied experimentally.
  • Activation and thermodynamic parameters for this reaction were determined.
  • The addition of Lewis bases was found to inhibit the reductive elimination process.
  • C-H oxidative addition at Al(i) centers proceeds via initial protonation.

Conclusions:

  • Ligand effects significantly influence reductive elimination from aluminum(III) centers.
  • Lewis bases act as inhibitors, highlighting their role in controlling reactivity.
  • The findings provide fundamental insights into main-group organometallic reaction mechanisms.