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Related Concept Videos

Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

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.
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

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,...
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

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

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, dissociates into a...
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...

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Updated: May 16, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Mapping the reduction-resistant solution components: ethers confirmed, tertiary amines revealed.

M A Orekhov1,2, S A Kislenko1,2

  • 1Joint Institute for High Temperatures of the Russian Academy of Sciences (JIHT RAS), Izhorskaya st. 13 Bd. 2, Moscow, 125412, Russia. maksim.orekhov@phystech.edu.

Physical Chemistry Chemical Physics : PCCP
|May 14, 2026
PubMed
Summary
This summary is machine-generated.

Tertiary amines, not just ethers, are highly reduction-resistant components for lithium metal anodes. This discovery broadens options for electrolyte engineering and functional additives in advanced battery technologies.

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Last Updated: May 16, 2026

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Published on: February 6, 2019

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Area of Science:

  • Materials Science
  • Electrochemistry
  • Computational Chemistry

Background:

  • Lithium metal anodes require electrolyte components resistant to reduction.
  • Ethers are currently the primary focus for reduction-resistant electrolyte additives.

Purpose of the Study:

  • To identify new classes of reduction-resistant molecules for lithium metal anodes.
  • To evaluate the potential of tertiary amines as electrolyte components.

Main Methods:

  • High-throughput quantum chemical screening of molecules.
  • Literature-based electrochemical analysis.
  • Lithium contact reflectometry for interfacial reactivity.

Main Results:

  • Ethers are confirmed as dominant reduction-resistant molecules.
  • Tertiary amines identified as the second-largest class of reduction-resistant components.
  • Experimental data validates low interfacial reactivity of tertiary amines.

Conclusions:

  • Tertiary amines are a promising, overlooked class of reduction-resistant materials for lithium metal batteries.
  • These findings expand the scope of electrolyte engineering for improved battery performance and stability.