Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Preparation of Nitriles01:12

Preparation of Nitriles

2.1K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.1K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.7K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
3.7K
Nitrosation of Enols01:19

Nitrosation of Enols

3.0K
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
3.0K
Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

4.4K
Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
4.4K
Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

3.9K
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
3.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.3K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.3K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Energy Transfer-Enabled Photocycloaddition of Oxazino Pyridines with Vinyl Azides to Access <i>Meta</i>-Functionalized Pyridines.

Journal of the American Chemical Society·2026
Same author

Pyridine to Pyridazine Skeletal Editing via CN-to-NN Atom-Pair Swap.

Journal of the American Chemical Society·2026
Same author

Reductive rearrangement of substituted quinolines to 2,3-disubstituted indoles enabled by water activation.

Chemical science·2026
Same author

Photoinduced Alcohol and Ketone Generation from Alkoxyaroylsilanes: Mechanistic Insights into Competing Radical Pathways.

JACS Au·2025
Same author

Activation of Cyanate Anions by Phosphine Radical Cations Enables Formal Hydrocarbamoylation of Alkenes.

Angewandte Chemie (International ed. in English)·2025
Same author

Reaction of Blatter and Verdazyl Radicals with Arynes: Synthesis and Investigation of N-Chiral, Antiaromatic Triazines, and Tetrazinones.

Angewandte Chemie (International ed. in English)·2025
Same journal

Synthetic Porous Carbons for High-Energy, High-Power Supercapacitors.

Chemical reviews·2026
Same journal

Navigating Misfolded Terrain: ER-Associated Degradation of Membrane Proteins.

Chemical reviews·2026
Same journal

Ink Design for Printing Perovskite Solar Cells and Modules.

Chemical reviews·2026
Same journal

Advanced Single-Atom Catalysts for Thermal-Catalytic C1 Chemistry.

Chemical reviews·2026
Same journal

Copper-Dependent Polysaccharide Monooxygenases: Mechanism and Function.

Chemical reviews·2026
Same journal

To Biotic or Abiotic: Biohybrid Systems for Artificial Photosynthesis.

Chemical reviews·2026
See all related articles

Related Experiment Video

Updated: Jul 19, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.2K

Organic Synthesis Using Nitroxides.

Dirk Leifert1, Armido Studer1

  • 1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149 Münster, Germany.

Chemical Reviews
|August 14, 2023
PubMed
Summary
This summary is machine-generated.

Nitroxides are stable radicals with diverse applications in organic synthesis, acting as oxidants, reductants, and radical terminators. Their unique reactivity across multiple oxidation states makes them valuable tools for chemists.

More Related Videos

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

10.3K

Related Experiment Videos

Last Updated: Jul 19, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.2K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

10.3K

Area of Science:

  • Organic Chemistry
  • Radical Chemistry
  • Catalysis

Background:

  • Nitroxides are stable radicals (R 1 R 2 N-O • ) with tunable redox properties.
  • Their stability arises from spin distribution and bulky substituents, preventing dimerization.
  • Nitroxides can exist in three oxidation states: radical, oxoammonium salt, and anion.

Purpose of the Study:

  • To review the versatile applications of nitroxides in organic synthesis.
  • To highlight their utility as catalysts and reagents in oxidation and reduction reactions.
  • To explore their role in radical chemistry, including radical termination and generation.

Main Methods:

  • Discussion of nitroxide preparation, structural diversity, and physical properties.
  • Examination of oxidation reactions catalyzed by nitroxides or their oxoammonium salts.
  • Analysis of nitroxide anions as reducing agents and alkoxyamines in radical transformations.

Main Results:

  • Nitroxides efficiently oxidize various functional groups, including alcohols, amines, enolates, and alkanes.
  • They serve as effective catalysts with terminal oxidants.
  • Nitroxide anions act as valuable reducing reagents.
  • Alkoxyamines derived from nitroxides enable controlled radical generation for synthesis.

Conclusions:

  • Nitroxides offer a versatile platform for diverse organic transformations.
  • Their ability to participate in multiple oxidation states expands their synthetic utility.
  • Nitroxide-mediated radical chemistry provides powerful strategies for complex molecule synthesis, including natural products.