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Related Concept Videos

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

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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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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

15.5K
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...
15.5K
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

9.2K
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 substituted...
9.2K
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

3.6K
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
3.6K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

3.0K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
3.0K
Isomerism02:43

Isomerism

25.0K
Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...
25.0K

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Related Experiment Video

Updated: Mar 13, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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A Migratory Ether Formation Route to Medium-Sized Sugar Mimetics.

Hao Jiang1, Li-Ping Xu1,2, Yan Fang1

  • 1Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.

Angewandte Chemie (International Ed. in English)
|October 14, 2016
PubMed
Summary

Researchers developed a new method for synthesizing complex polyol cyclic ethers, crucial for biomolecules. This migratory ether formation strategy creates medium-sized sugar mimetics previously inaccessible.

Keywords:
medium-sized ringsmigratory ether formationring-opening reactionssugartrimethyl alumininum

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Synthetic Chemistry

Background:

  • Polyol-substituted cyclic ethers are essential components of biomolecules.
  • The biological function of these ethers depends on the precise positioning and stereochemistry of their hydroxyl groups.
  • Existing synthetic methods are insufficient for creating highly substituted cyclic ethers.

Purpose of the Study:

  • To develop a general synthetic route for medium-sized polyol cyclic ethers.
  • To explore a novel migratory ether formation strategy for accessing complex cyclic ether structures.
  • To synthesize novel sugar mimetics with potential biological applications.

Main Methods:

  • Utilized a migratory ether formation strategy involving epoxide opening.
  • Employed trimethylaluminum (Me3Al) to catalyze an unprecedented ether addition reaction.
  • Incorporated monosaccharides as hemiacetal auxiliaries to expand sugar ring structures.

Main Results:

  • Achieved the synthesis of medium-sized polyol cyclic ethers with multiple substituents.
  • Demonstrated an unprecedented ether addition reaction and a 1,3-methyl shift yielding 2-deoxyribital products.
  • Successfully expanded monosaccharide rings to form 9- to 11-membered sugar analogues.

Conclusions:

  • The developed migratory ether formation strategy provides a versatile route to complex polyol cyclic ethers.
  • This method opens access to previously untapped chemical space of medium-sized sugar mimetics.
  • The synthesized sugar analogues hold potential for diverse biological and medicinal chemistry applications.