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Related Concept Videos

Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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 amide...
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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...
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...

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Related Experiment Video

Updated: Jun 15, 2026

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

N-acyliminium intermediates in solid-phase synthesis.

Sebastian T Le Quement1, Rico Petersen, Morten Meldal

  • 1Department of Chemistry, Technical University of Denmark, Kemitorvet, Building 201, DK-2800 Kgs. Lyngby, Denmark.

Biopolymers
|March 13, 2010
PubMed
Summary
This summary is machine-generated.

This review highlights N-acyliminium ions, powerful synthetic intermediates, and their limited use in solid-phase synthesis. It covers methods for generating these ions on solid supports for creating valuable molecules.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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Published on: August 22, 2018

Area of Science:

  • Synthetic organic chemistry
  • Medicinal chemistry

Background:

  • N-acyliminium ions are versatile intermediates in organic synthesis.
  • Their application in solution-phase chemistry is well-documented.
  • Solid-phase synthesis applications for these ions are underexplored.

Purpose of the Study:

  • To review the current literature on N-acyliminium ion generation and utilization in solid-phase synthesis.
  • To showcase methods for creating these reactive intermediates on solid supports.
  • To demonstrate their utility in synthesizing diverse molecular structures.

Main Methods:

  • Literature review of N-acyliminium ion chemistry on solid supports.
  • Analysis of methods for generating N-acyliminium intermediates on solid phase.
  • Examination of subsequent reactions for molecule elaboration.

Main Results:

  • Several methods exist for generating N-acyliminium ions on solid supports.
  • These intermediates can be effectively used to synthesize complex molecules.
  • Applications include the creation of peptidomimetics and heterocycles.

Conclusions:

  • Solid-phase generation of N-acyliminium ions is a viable and powerful strategy.
  • This approach facilitates the synthesis of pharmacologically relevant compounds.
  • Further exploration of these methods is warranted for drug discovery.