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Related Concept Videos

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.
Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions generating free carboxylic acid...
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
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...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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Related Experiment Video

Updated: Jun 23, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

C═C/N═O Metathesis Enables Oxidative Decarboxylation.

Bence B Botlik1, Adriana Neves Vieira1, Benjamin Mitschke1

  • 1D-CHAB, Laboratory of Organic Chemistry, ETH Zürich, Vladimir Prelog Weg 1-5, Zürich 8093, Switzerland.

Journal of the American Chemical Society
|June 22, 2026
PubMed
Summary
This summary is machine-generated.

A novel iron-catalyzed C═C/N═O metathesis enables mild oxidative decarboxylation of carboxylic acids. This earth-abundant catalyzed reaction is scalable, air-stable, and broadly applicable, even in late-stage drug synthesis.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Area of Science:

  • Synthetic organic chemistry
  • Catalysis
  • Green chemistry

Background:

  • Metathesis reactions involving (2 + 2) cycloaddition-(2 + 2) cycloreversion are crucial in synthesis.
  • Limited substrate scope has historically restricted the application of this reaction class.

Purpose of the Study:

  • To develop a novel iron(II)-catalyzed C═C/N═O metathesis reaction.
  • To apply this new reaction to the mild oxidative decarboxylation of carboxylic acids.

Main Methods:

  • Iron(II)-catalyzed C═C/N═O metathesis reaction development.
  • Application to oxidative decarboxylation of carboxylic acids.
  • Mechanistic studies including ReactIR and computational analysis.

Main Results:

  • A novel iron-catalyzed C═C/N═O metathesis was successfully designed and implemented.
  • The reaction enables mild, air-stable, one-pot oxidative decarboxylation of carboxylic acids using an earth-abundant iron catalyst.
  • Broad functional group tolerance, scalability, and late-stage applicability to drug molecules were demonstrated.
  • The method was extended to ester synthesis from α-aryloxy and α-alkoxy carboxylic acids.

Conclusions:

  • The developed iron-catalyzed metathesis offers a versatile and sustainable method for carboxylic acid functionalization.
  • This approach provides access to ketones and imines, expanding synthetic possibilities.
  • The reaction's efficiency, scalability, and broad applicability highlight its potential impact on synthetic chemistry and drug discovery.