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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...
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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 carbon to...
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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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.
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Anodic Cyclizations and Umpolung Reactions Involving Imines.

Zach Medcalf1, Essence G Redd2, Jaemyeong Oh2

  • 1Department of Chemistry, Washington University in Saint Louis, Saint Louis, Missouri 63130, United States.

Organic Letters
|May 30, 2023
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Summary

Anodic cyclization reactions can be channeled into new synthetic pathways by controlling a second electron oxidation step. This study demonstrates a novel method for the asymmetric synthesis of cyclic amines using this approach.

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Area of Science:

  • Organic electrochemistry
  • Synthetic organic chemistry

Background:

  • Anodic cyclization reactions are crucial in organic synthesis.
  • A key step involves a second electron oxidation downstream of cyclization.
  • This step offers potential for controlling reaction pathways.

Purpose of the Study:

  • To explore new synthetic pathways using anodic cyclization.
  • To demonstrate the utility of a second electron oxidation step in directing reactivity.
  • To enable the asymmetric synthesis of cyclic amines via anodic cyclization.

Main Methods:

  • Utilizing anodic cyclization with a focus on the second electron oxidation.
  • Reversing the typical reactivity of imine groups within the reaction mechanism.
  • Developing conditions for asymmetric synthesis.

Main Results:

  • Successfully channeled an anodic cyclization reaction down a new synthetic pathway.
  • Demonstrated the reversal of imine group reactivity.
  • Established a method for the asymmetric synthesis of cyclic amines.

Conclusions:

  • The second electron oxidation step is a powerful tool for controlling anodic cyclization pathways.
  • This work provides a novel route to asymmetrically synthesized cyclic amines.
  • The methodology broadens the scope of electroorganic synthesis.