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Related Concept Videos

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α...
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Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

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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...
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Acid Halides to Amides: Aminolysis01:07

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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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Preparation of Amines: Alkylation of Ammonia and Amines01:30

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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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.
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Updated: May 4, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
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Ketene reactions with tertiary amines.

Annette D Allen1, John Andraos, Thomas T Tidwell

  • 1Department of Chemistry, University of Toronto , Toronto, Ontario M5S 3H6, Canada.

The Journal of Organic Chemistry
|December 24, 2013
PubMed
Summary
This summary is machine-generated.

Tertiary amines and arylketenes form zwitterions, which then undergo amine-catalyzed dealkylation to yield amides. Methyl and ethyl group loss occur via displacement, while isopropyl group loss involves elimination.

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Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms

Background:

  • Tertiary amines are crucial in organic synthesis.
  • Arylketenes are reactive intermediates.
  • Understanding reaction pathways is key to controlling chemical transformations.

Purpose of the Study:

  • To investigate the reaction mechanism between tertiary amines and arylketenes.
  • To elucidate the pathways of amine dealkylation in amide formation.
  • To explore the role of steric and electronic factors in directing dealkylation.

Main Methods:

  • Kinetic studies in acetonitrile.
  • Spectroscopic observation of zwitterionic intermediates.
  • Computational studies (e.g., DFT) to predict reaction pathways.
  • Analysis of dealkylation products.

Main Results:

  • Rapid, reversible formation of observable zwitterions between tertiary amines and arylketenes.
  • Amine-catalyzed dealkylation of zwitterions yields N,N-disubstituted amides.
  • N-methyldialkylamines predominantly lose methyl groups via displacement.
  • Triethylamine shows displacement of ethyl groups.
  • Diisopropylethylamine with phenylketene shows preferential elimination of isopropyl groups.
  • Quinuclidine forms stable zwitterions, modeling alkaloid catalysis.

Conclusions:

  • The reaction proceeds via zwitterionic intermediates followed by amine-catalyzed dealkylation.
  • Dealkylation mechanisms (displacement vs. elimination) are influenced by the amine structure and substituents.
  • Computational studies accurately predict the observed regioselectivity of dealkylation.
  • The quinuclidine-arylketene system serves as a valuable model for understanding cinchona alkaloid-catalyzed reactions.