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Crown Ethers02:36

Crown Ethers

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Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
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Preparation of Epoxides03:00

Preparation of Epoxides

7.7K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
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Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

7.4K
Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more...
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

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Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...
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Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

11.0K
Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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Related Experiment Video

Updated: May 6, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

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A Stepwise Approach to 1,4,10,13-Tetraaza-18-Crown-6 Ether.

Pieter Troosters1,2, Lara Bruneel1,2, Wim Dehaen2

  • 1Nuclear Energy Technology, Belgian Nuclear Research Centre (SCK CEN), Mol, Belgium.

Chemistryopen
|May 5, 2026
PubMed
Summary

A new two-step synthesis of tetraaza-18-crown-6 ether significantly improves yield by minimizing side products. This optimized macrocyclization method offers a more efficient alternative to the traditional one-step approach.

Keywords:
crown compoundsmacrocyclesmacrocyclizationstepwise synthesistetraaza‐18‐crown‐6 ether

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Area of Science:

  • Organic Chemistry
  • Macrocyclic Chemistry

Background:

  • The synthesis of tetraaza-18-crown-6 ether is crucial for various applications.
  • Current one-step macrocyclization methods suffer from low yields due to significant side product formation.

Purpose of the Study:

  • To develop and evaluate a two-step synthesis strategy for tetraaza-18-crown-6 ether.
  • To optimize reaction conditions to enhance yield and reduce undesired byproducts.

Main Methods:

  • A two-step reaction pathway was designed for macrocyclization.
  • Reaction conditions were systematically optimized to favor the desired product formation.
  • The formation of a nine-membered ring byproduct was specifically targeted for reduction.

Main Results:

  • The two-step macrocyclization approach yielded a 50% improvement.
  • Optimization reduced cyclization to the undesired nine-membered ring by a factor of eight.
  • A yield of 28% was achieved even without column chromatography, surpassing the 16% yield of the one-step method.

Conclusions:

  • The evaluated two-step synthesis offers a significantly higher yield for tetraaza-18-crown-6 ether compared to the one-step method.
  • Optimized conditions in the two-step approach effectively suppress side product formation.
  • This improved synthetic route presents a more efficient method for producing tetraaza-18-crown-6 ether.