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Related Concept Videos

Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
Aldehydes and Ketones with Water: Hydrate Formation01:20

Aldehydes and Ketones with Water: Hydrate Formation

An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.

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Related Experiment Video

Updated: Jul 13, 2026

Transport Properties of Ibuprofen Encapsulated in Cyclodextrin Nanosponge Hydrogels: A Proton HR-MAS NMR Spectroscopy Study
10:10

Transport Properties of Ibuprofen Encapsulated in Cyclodextrin Nanosponge Hydrogels: A Proton HR-MAS NMR Spectroscopy Study

Published on: August 15, 2016

Per-O-(3-hydroxy)propyl-beta-cyclodextrin: a cyclodextrin derivative bearing only primary hydroxyl groups.

Nezha Badi1, Philippe Guégan

  • 1Laboratoire Matériaux Polymères aux Interfaces-LRP, UMR CNRS 7581, Université d'Evry Val d'Essonne, Evry, France.

Carbohydrate Research
|July 7, 2007
PubMed
Summary

Researchers synthesized a modified beta-cyclodextrin with primary hydroxyl groups. This novel macro-initiator enables the creation of star-shaped polymers via ethylene oxide polymerization.

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Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications
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Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications

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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
08:46

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

Published on: July 26, 2018

Related Experiment Videos

Last Updated: Jul 13, 2026

Transport Properties of Ibuprofen Encapsulated in Cyclodextrin Nanosponge Hydrogels: A Proton HR-MAS NMR Spectroscopy Study
10:10

Transport Properties of Ibuprofen Encapsulated in Cyclodextrin Nanosponge Hydrogels: A Proton HR-MAS NMR Spectroscopy Study

Published on: August 15, 2016

Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications
09:22

Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications

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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
08:46

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

Published on: July 26, 2018

Area of Science:

  • Supramolecular Chemistry
  • Polymer Chemistry
  • Organic Synthesis

Background:

  • Cyclodextrins are cyclic oligosaccharides with unique host-guest properties.
  • Modifying cyclodextrins can create novel materials with tailored functionalities.
  • Controlled polymerization requires well-defined initiators for predictable polymer architectures.

Purpose of the Study:

  • To synthesize a novel beta-cyclodextrin derivative with exclusively primary hydroxyl groups.
  • To utilize this modified cyclodextrin as a macro-initiator for anionic polymerization.
  • To investigate the formation of star-shaped polymers from ethylene oxide.

Main Methods:

  • Per-O-allylation of natural beta-cyclodextrin using sodium hydride and allyl bromide.
  • Hydroboration-oxidation of the allyl groups using 9-BBN, sodium hydroxide, and hydrogen peroxide.
  • Anionic polymerization of ethylene oxide initiated by the modified cyclodextrin.

Main Results:

  • Successful synthesis of per-O-(3-hydroxy)propyl-beta-cyclodextrin in approximately 65% yield.
  • The modified cyclodextrin exclusively possesses primary hydroxyl groups.
  • Demonstrated utility as a macro-initiator for ethylene oxide polymerization, yielding star-shaped polymers.

Conclusions:

  • A novel, selectively functionalized beta-cyclodextrin derivative was synthesized.
  • The resulting macro-initiator offers uniform initiation sites for polymerization.
  • This approach provides a pathway to precisely engineered star polymers with potential applications in materials science.