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

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

3.8K
The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
3.8K
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

8.1K
The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
8.1K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.0K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
2.0K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.9K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
18.9K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

16.4K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
16.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.8K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.8K

You might also read

Related Articles

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

Sort by
Same author

Isolation and genomic analysis of otomycosis pathogens, and genomics-informed antimicrobial peptide design with potential therapeutic applications.

BMC microbiology·2026
Same author

Engineering manganese-based immune amplifier for chemoimmunotherapy of peritoneal metastatic colorectal cancer.

Materials today. Bio·2026
Same author

[Research on the changing trends of filter inlet pressure and extracorporeal circuit coagulation degree in patients with sepsis-induced coagulopathy undergoing continuous renal replacement therapy].

Zhonghua wei zhong bing ji jiu yi xue·2026
Same author

Synergistic microwave enzymatic immersion pretreatment of apple slices: Effects on mass transfer, enzyme activity, and digestive bioaccessibility.

Food chemistry·2026
Same author

Biochemical, transcriptomics, and metabolomics analyses reveal coordinated antioxidant responses in Penicillium digitatum under MAP-simulated gas conditions.

Food microbiology·2026
Same author

Synergistic regulation of P. eryngii quality and protein properties by dielectric-guided gradient conversion drying and ultrasound-assisted functional rehydration of by-products.

Food research international (Ottawa, Ont.)·2026

Related Experiment Video

Updated: Sep 16, 2025

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

13.8K

Aluminacyclopropene-phosphine complex: a carbene-exchange reagent.

Huihui Xu1, José Miguel León Baeza1,2, Antoine Baceiredo1

  • 1Laboratoire Hétérochimie Fondamentale et Appliquée (UMR 5069), Université de Toulouse, CNRS 118 Route de Narbonne F-31062 Toulouse France tsuyoshi.kato@utoulouse.fr.

Chemical Science
|July 10, 2025
PubMed
Summary

This study introduces a novel aluminacyclopropene-phosphine complex that facilitates unprecedented "carbene-to-carbene" transformations. This breakthrough enables skeletal modifications of stable N-heterocyclic carbenes (NHCs) via atomic carbon transfer.

More Related Videos

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.6K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.4K

Related Experiment Videos

Last Updated: Sep 16, 2025

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

13.8K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.6K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.4K

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Carbene Chemistry

Background:

  • N-heterocyclic carbenes (NHCs) are stable ligands and organocatalysts.
  • Skeletal modifications of NHCs via carbene exchange reactions are rare due to their high stability.

Purpose of the Study:

  • To report novel carbene-to-carbene transformations using an aluminacyclopropene-phosphine complex.
  • To demonstrate skeletal modification of stable carbenes.

Main Methods:

  • Reaction of aluminacyclopropene-phosphine complex 1 with N-heterocyclic carbene (NHC) 2.
  • Atomic carbon transfer from NHC to an alkyne fragment within the Al(iii) coordination sphere.
  • Transformation of a stable cyclopropenylidene into a reactive acyclic carbene.

Main Results:

  • Complex 1 mediates carbene-to-carbene transformations.
  • A cyclopropenylidene (4) is formed via atomic carbon transfer from NHC 2.
  • A stable (diamino)cyclopropenylidene (7) is converted into a reactive acyclic (amino)carbene (8).

Conclusions:

  • The aluminacyclopropene-phosphine complex enables unique carbene exchange reactions.
  • This work expands the synthetic utility of stable carbenes.
  • Isolated crystalline acyclic carbene 8 demonstrates the reactivity enabled by the complex.