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Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

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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.
6.4K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.8K
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...
4.8K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

8.6K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
8.6K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.1K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
3.1K
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

10.7K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal, such as sodium,...
10.7K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.4K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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Ammonia decomposition catalysis using non-stoichiometric lithium imide.

Joshua W Makepeace1,2, Thomas J Wood1, Hazel M A Hunter1

  • 1ISIS Facility , Rutherford Appleton Laboratory , Harwell Oxford , Didcot , OX11 0QX , UK .

Chemical Science
|December 9, 2017
PubMed
Summary

Non-stoichiometric lithium imide acts as a highly active catalyst for producing high-purity hydrogen from ammonia. This novel catalyst incorporates hydrogen into its bulk, outperforming existing materials in ammonia decomposition.

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Area of Science:

  • Catalysis
  • Materials Science
  • Chemical Engineering

Background:

  • Ammonia decomposition is a key process for hydrogen production.
  • Developing efficient and selective catalysts is crucial for industrial applications.
  • Existing catalysts often face limitations in activity and stability.

Purpose of the Study:

  • To investigate the catalytic activity of non-stoichiometric lithium imide for ammonia decomposition.
  • To understand the structural and chemical changes of the catalyst during the reaction.
  • To explore the mechanism of hydrogen incorporation in the catalyst.

Main Methods:

  • Synthesis and characterization of non-stoichiometric lithium imide.
  • Ammonia decomposition reaction testing under various conditions.
  • Neutron powder diffraction for in-situ structural analysis.
  • Gas chromatography for product analysis.

Main Results:

  • Non-stoichiometric lithium imide exhibits superior ammonia decomposition activity compared to other catalysts.
  • The catalyst deviates from pure imide stoichiometry under ammonia flow, with activity observed across a range of compositions.
  • Significant hydrogen exchange and incorporation into the bulk catalyst material were observed.

Conclusions:

  • Non-stoichiometric lithium imide is a highly effective catalyst for high-purity hydrogen production from ammonia.
  • The unique hydrogen incorporation mechanism offers a new pathway for catalyst design.
  • This finding expands the scope of amide-based ammonia decomposition catalysts to include imide-forming systems.