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

19.1K
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.
19.1K
Carbocations02:10

Carbocations

11.9K
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...
11.9K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.1K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
9.1K
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

3.9K
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...
3.9K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.2K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.2K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.5K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.5K

You might also read

Related Articles

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

Sort by
Same author

Anionic T-Shaped Platinum(0) Pincer Complexes and Platinum(I) Intermediates in Radical Reactions With Alkyl Halides.

Angewandte Chemie (International ed. in English)·2026
Same author

Small and Prototypic: Dimethyl Ether in Lithiumorganics─Insights from Experimental Charge Density Studies.

Inorganic chemistry·2026
Same author

Charge Density and Magnetic Properties in Cobalt(II) Single-Molecule Magnets: Impact of Ligand Substitution.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
Same author

Isolation and Reactivity of a Square-Planar Trisamido Silane.

Angewandte Chemie (International ed. in English)·2026
Same author

Bicyclic (Alkyl)(Amino)Imine-Anchored Diphosphine and Its Radical Cation.

Inorganic chemistry·2026
Same author

Bis-Dichlorosilyl Functionalized C<sub>4</sub>-Cumulene With Unique Bonding Scenario.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026

Related Experiment Video

Updated: Sep 28, 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

A Carbene-Stabilized Boryl-Phosphinidene.

Samir Kumar Sarkar1, Subrata Kundu2, Mohd Nazish1

  • 1Institut für Anorganische Chemie, Universität Göttingen, Tammannstrasse 4, 37077, Göttingen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 31, 2022
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel carbene-stabilized boryl phosphinidenes. These compounds exhibit unique double Lewis base properties due to two distinct lone pairs on the phosphorus atom.

Keywords:
bent geometryboryl phosphinidenescyclic(alkyl)(amino)carbenesmolecular orbitalsphosphaalkenes

More Related Videos

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

7.9K
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

11.0K

Related Experiment Videos

Last Updated: Sep 28, 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
Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

7.9K
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

11.0K

Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Carbene Chemistry

Background:

  • Carbene-stabilized phosphinidenes are an emerging class of reactive intermediates.
  • Understanding their electronic structure and reactivity is crucial for developing new synthetic methodologies.

Purpose of the Study:

  • To synthesize and characterize novel carbene-stabilized boryl phosphinidenes.
  • To investigate the electronic properties and Lewis basicity of these unique compounds.

Main Methods:

  • Synthesis via reaction of dimethyl cyclic(alkyl)(amino)carbene (Me2-cAAC) with dihaloaryl boranes.
  • Characterization using X-ray crystallography.
  • Quantum mechanical studies to elucidate electronic structure.

Main Results:

  • Successfully synthesized and characterized three carbene-stabilized boryl phosphinidenes (1-3).
  • X-ray crystallography confirmed the molecular structures.
  • Quantum mechanical calculations revealed two lone pairs on the phosphorus center: one sigma-type and one 'hidden' pi-type.
  • The pi-type lone pair exhibits higher basicity than the sigma-type lone pair.

Conclusions:

  • The synthesized compounds are stable carbene-stabilized boryl phosphinidenes.
  • These molecules function as double Lewis bases.
  • The electronic structure dictates a unique reactivity profile with potential applications in catalysis and synthesis.