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

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Nuclear Stability03:18

Nuclear Stability

Protons and neutrons, collectively called nucleons, are packed together tightly in a nucleus. With a radius of about 10−15 meters, a nucleus is quite small compared to the radius of the entire atom, which is about 10−10 meters. Nuclei are extremely dense compared to bulk matter, averaging 1.8 × 1014 grams per cubic centimeter. If the earth’s density were equal to the average nuclear density, the earth’s radius would be only about 200 meters.
To hold positively charged protons together in the...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

You might also read

Related Articles

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

Sort by
Same author

Organometallic Complexes with an Indolo[2,3-<i>c</i>]Quinoline-Derived Ligand: From Structural Features and Solution Speciation to Nanoformulation for Enhanced Therapeutic Potential.

Inorganic chemistry·2026
Same author

Copper(II) complexes of indolo[2,3-c]quinoline-derived Schiff bases: Insight into the mechanism of their antiproliferative activity.

European journal of medicinal chemistry·2026
Same author

Quest for 2,3-Secopyramidane: Computations Hint at Elusive Structure during Skattebo̷l Rearrangement of Vinylcyclopropylidene∇.

The Journal of organic chemistry·2026
Same author

Copper(II) complex with a redox-noninnocent Schiff base bearing a tetraphenyldisiloxane unit: synthesis, structure and catalytic oxidation of cyclohexane.

Dalton transactions (Cambridge, England : 2003)·2025
Same author

Physical properties and cytotoxicity of Cu(II) and Zn(II) complexes with a TMS-substituted indolo[2,3-<i>c</i>]quinoline-derived Schiff base.

Dalton transactions (Cambridge, England : 2003)·2025
Same author

<sup>187</sup>Os nuclear resonance scattering to explore hyperfine interactions and lattice dynamics for biological applications.

Science advances·2025
Same journal

Tunable Palladium-Catalyzed [2π + 2σ] Cycloaddition/Alder-Ene Reactions of Vinylbicyclo[1.1.0]butanes with Cyclic <i>N</i>-Sulfonylimines.

The Journal of organic chemistry·2026
Same journal

Engineering a Carboxylesterase for Enantioselective Acyl Transfer Reaction.

The Journal of organic chemistry·2026
Same journal

Visible-Light-Promoted Trifluoromethylation/Ring-Opening Reaction of Vinylcyclopropanes by an EDA Complex.

The Journal of organic chemistry·2026
Same journal

Controlling Chemical Dynamics of Molecular Assemblies through Nanoconfinement: <i>o</i>-Nitrosocumene@Pd Nanocage.

The Journal of organic chemistry·2026
Same journal

Solvent Stabilization of Protic Oxonium/Ammonium Intermediates in Cation Radical Cyclization Reactions Investigated via Computational Approaches.

The Journal of organic chemistry·2026
Same journal

Concise Synthesis of Pyrano/Benzopyrano[2,3-<i>c</i>]pyrazol-6-ones via Ir/Rh-Catalyzed C-H Activation and Tandem Annulation.

The Journal of organic chemistry·2026
See all related articles

Related Experiment Video

Updated: May 30, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Quest for even higher stabilized foiled carbenes.

Kuan-Jen Su1, Mirjana Pačar, Jean-Luc Mieusset

  • 1Chair of Physical Organic and Structural Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, Austria.

The Journal of Organic Chemistry
|August 4, 2011
PubMed
Summary
This summary is machine-generated.

Researchers theoretically identified novel foiled carbene structures stabilized by intramolecular interactions. These tetracyclic compounds are predicted to be highly stable, with a precursor synthesized and a bicyclopropylidene dimer isolated.

More Related Videos

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

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Related Experiment Videos

Last Updated: May 30, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Carbenes are reactive intermediates with a divalent carbon atom.
  • Stabilized carbenes are of interest for their unique reactivity and potential applications.
  • Foiled carbenes represent a class with intramolecular stabilizing interactions.

Purpose of the Study:

  • To theoretically locate and characterize novel foiled carbene structures.
  • To investigate the stability and potential for intramolecular rearrangements of these species.
  • To synthesize a precursor and explore the reactivity of foiled carbenes.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed to locate and analyze carbene structures.
  • A multi-step synthesis was performed to prepare a dibromocyclopropane precursor.
  • Chemical treatment of the precursor was carried out to generate and isolate carbene species.

Main Results:

  • DFT calculations identified tetracyclic foiled carbene structures with strong stabilizing interactions.
  • These species are predicted to reside in a deep potential energy well, indicating high stability.
  • A 12-step synthesis yielded the intended dibromocyclopropane precursor.
  • Treatment with methyllithium resulted in the isolation of a bicyclopropylidene, a formal carbene dimer.

Conclusions:

  • Novel, highly stable foiled carbene structures have been theoretically identified.
  • The synthetic accessibility of a suitable precursor was demonstrated.
  • The reactivity of the generated carbene led to dimerization, highlighting its propensity for further reactions.