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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: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

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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...
7.7K
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

2.4K
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
2.4K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.2K
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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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.0K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.0K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.7K
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,...
3.7K

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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
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Enantioselective methodologies using N-carbamoyl-imines.

Jan Vesely1, Ramon Rios

  • 1Department of Organic Chemistry, Charles University, Hlavova 2030, 128 43 Praha 2, Czech Republic. jxvesely@natur.cuni.cz.

Chemical Society Reviews
|November 5, 2013
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Summary

N-carbamoyl imines enhance nucleophilic addition reactions, enabling efficient enantioselective synthesis of amine derivatives. This review covers key methods utilizing these versatile imines for creating valuable organic compounds.

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Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis

Background:

  • Nucleophilic addition to imines is crucial for synthesizing amine derivatives.
  • Low imine reactivity necessitates strategies like using electron-withdrawing groups.
  • N-carbamoyl imines offer enhanced reactivity and facile deprotection.

Purpose of the Study:

  • To review enantioselective methods employing N-carbamoyl imines.
  • To focus on synthetically useful protocols for organic compound synthesis.

Main Methods:

  • Utilizing N-carbamoyl imines in nucleophilic addition reactions.
  • Developing and applying asymmetric methodologies.

Main Results:

  • N-carbamoyl imines demonstrate increased reactivity towards nucleophiles.
  • Successful application in enantioselective synthesis of diverse organic compounds.
  • Carbamoyl group removal is generally straightforward in target molecules.

Conclusions:

  • N-carbamoyl imines are highly effective in enantioselective synthesis.
  • These methods provide synthetically valuable routes to chiral amines.
  • Further exploration of N-carbamoyl imine chemistry is warranted.