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Related Concept Videos

Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

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

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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

Aldehydes and Ketones with Amines: Imine Formation Mechanism

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...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

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

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.

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Related Experiment Video

Updated: Jun 12, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

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

Published on: October 18, 2019

Enamine-Mediated [2 + 2] Skeletal Editing for the Synthesis of Eight-Membered Iminosugars.

Weilin Yang1, Likai Zhou1,2, Pei Zhao1

  • 1Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding, Hebei 071002, P. R. China.

Organic Letters
|June 11, 2026
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel eight-membered iminosugars using a one-pot cycloaddition and ring expansion strategy. This method offers a convenient route to complex nitrogen-containing heterocycles.

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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Iminosugars are important carbohydrate mimics with diverse biological activities.
  • The synthesis of eight-membered nitrogen-containing heterocycles remains challenging.
  • Developing efficient synthetic routes to novel iminosugar scaffolds is crucial.

Purpose of the Study:

  • To develop a novel one-pot strategy for the synthesis of eight-membered iminosugars.
  • To explore a skeletal editing approach for constructing uncommon nitrogen-containing heterocycles.
  • To provide a convenient method for accessing complex iminosugar derivatives.

Main Methods:

  • One-pot [2+2] cycloaddition reaction between enamine and alkyne moieties.
  • Subsequent ring expansion of the cycloadduct.
  • Utilizing amines, functionalized sugars, and butynoate esters as starting materials.

Main Results:

  • Successful construction of target eight-membered iminosugars in a single pot.
  • Demonstration of a convenient skeletal editing strategy.
  • Access to uncommon eight-membered nitrogen-containing heterocyclic scaffolds.

Conclusions:

  • The developed one-pot method is efficient for synthesizing eight-membered iminosugars.
  • This strategy provides a valuable tool for accessing novel nitrogen-containing heterocycles.
  • The approach offers a convenient route for skeletal editing in organic synthesis.