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Related Concept Videos

Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Oxidation of Alcohols02:37

Oxidation of Alcohols

In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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.
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
Intramolecular Aldol Reaction01:18

Intramolecular Aldol Reaction

Intramolecular aldol reaction occurs in dicarbonyl compounds such as dialdehydes, diketones, and keto-aldehydes. The dicarbonyl compounds possess more than one nucleophilic ⍺ carbon for the base to deprotonate and form the enolates. For example, in symmetrical diketones, there are four ⍺ carbons. Hence, four types of enolates are possible when treated with a base. However, since the molecule is symmetrical, the enolates formed on either side of one carbonyl group are equivalent to those formed...

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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Published on: May 27, 2015

Cyclodextrin aldehydes are oxidase mimics.

Thomas Hauch Fenger1, Jeannette Bjerre, Mikael Bols

  • 1Department of Chemistry and Nanoscience Center, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen.

Chembiochem : a European Journal of Chemical Biology
|September 10, 2009
PubMed
Summary
This summary is machine-generated.

New cyclodextrin aldehydes efficiently catalyze aminophenol oxidation using hydrogen peroxide, outperforming previous cyclodextrin ketones. The best catalyst, 2-O-ethoxy-2-al-beta-cyclodextrin, shows enhanced binding of hydrogen peroxide for superior catalytic activity.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Catalysis
  • Green Chemistry

Background:

  • Cyclodextrins are cyclic oligosaccharides with a hydrophobic cavity and hydrophilic exterior, widely used in catalysis.
  • Previous studies demonstrated cyclodextrin ketones as catalysts for oxidation reactions.
  • Hydrogen peroxide is a green oxidant, but its efficient utilization in catalysis remains a challenge.

Purpose of the Study:

  • To synthesize and evaluate novel cyclodextrin aldehydes as catalysts for aminophenol oxidation.
  • To compare the catalytic efficiency of cyclodextrin aldehydes with cyclodextrin ketones.
  • To investigate the kinetic mechanism and structure-activity relationships of the novel catalysts.

Main Methods:

  • Synthesis of various cyclodextrin derivatives functionalized with aldehyde groups at primary and secondary rims.
  • Catalytic oxidation of aminophenols using hydrogen peroxide in the presence of synthesized cyclodextrin aldehydes.
  • Kinetic studies to determine Michaelis-Menten parameters.
  • Spectroscopic analysis to confirm catalyst structure and binding interactions.

Main Results:

  • Several cyclodextrin aldehydes were successfully synthesized and characterized.
  • The synthesized cyclodextrin aldehydes effectively catalyzed the oxidation of aminophenols with hydrogen peroxide.
  • Catalysis followed Michaelis-Menten kinetics, indicating enzyme-like behavior.
  • 2-O-ethoxy-2-al-beta-cyclodextrin (compound 22) emerged as the most potent catalyst.
  • Aldehyde-based catalysts demonstrated superior activity compared to previously reported ketone analogues.
  • Enhanced covalent binding of hydrogen peroxide by the aldehyde groups was identified as the key factor for improved catalysis.

Conclusions:

  • Cyclodextrin aldehydes represent a promising class of catalysts for oxidation reactions.
  • The enhanced catalytic activity is attributed to the strong covalent interaction of aldehyde groups with hydrogen peroxide.
  • These findings offer a new avenue for developing efficient and green catalytic systems.
  • Further research into structure optimization could lead to even more effective catalysts.