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

21.7K
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.
21.7K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

4.3K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
4.3K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

12.0K
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.
12.0K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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

3.9K
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...
3.9K
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

5.5K
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...
5.5K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

3.9K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
3.9K

You might also read

Related Articles

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

Sort by
Same author

Construction of a Diverse Range of Boron Heterocycles via Ring Expansion of a Carboranyl-Substituted 9-Borafluorene.

Chemistry (Weinheim an der Bergstrasse, Germany)·2023
Same author

Towards the catalytic activation of inert small molecules by main-group ambiphiles.

Communications chemistry·2023
Same author

Air and Moisture Stable <i>para</i>- and <i>ortho</i>-Quinodimethane Derivatives Derived from <i>bis</i>-<i>N</i>-Heterocyclic Olefins.

Organic letters·2023
Same author

C-C and C-N Bond Activation, Lewis-Base Coordination and One- and Two-Electron Oxidation at a Linear Aminoborylene.

Chemistry (Weinheim an der Bergstrasse, Germany)·2022
Same author

Backbone-controlled LUMO energy induces intramolecular C-H activation in <i>ortho</i>-bis-9-borafluorene-substituted phenyl and <i>o</i>-carboranyl compounds leading to novel 9,10-diboraanthracene derivatives.

Chemical science·2022
Same author

On the Reactivity of Phosphaalumenes towards C-C Multiple Bonds.

Angewandte Chemie (International ed. in English)·2022

Related Experiment Video

Updated: Mar 15, 2026

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

8.3K

Direct Conversion from Terminal Borylene into Terminal Phosphinidene.

Holger Braunschweig1,2, J Oscar C Jimenez-Halla3, Krzysztof Radacki4,5

  • 1Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany. h.braunschweig@uni-wuerzburg.de.

Angewandte Chemie (International Ed. in English)
|September 14, 2016
PubMed
Summary

Researchers synthesized the first terminal manganese phosphinidene complex from an alkylborylene precursor. This study details its structure, bonding, and reaction mechanism using experimental and computational methods.

Keywords:
boranesborylene complexesiminophosphinesmanganese complexesphosphinidene complexes

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

14.3K
[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

9.9K

Related Experiment Videos

Last Updated: Mar 15, 2026

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

8.3K
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

14.3K
[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

9.9K

Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Phosphorus Chemistry

Background:

  • Terminal phosphinidene complexes are rare and highly reactive intermediates.
  • Manganese complexes offer unique electronic properties for catalysis and synthesis.
  • Previous synthetic routes to phosphinidene complexes have limitations.

Purpose of the Study:

  • To report the first quantitative synthesis of a terminal manganese phosphinidene complex.
  • To elucidate the structural and bonding characteristics of this novel complex.
  • To investigate the reaction mechanism involving the phosphinidene species.

Main Methods:

  • Synthesis of the terminal alkylborylene complex precursor.
  • Reaction of the precursor with a suitable manganese source.
  • Characterization using X-ray crystallography and spectroscopy.
  • Computational studies including Density Functional Theory (DFT) calculations.

Main Results:

  • Successful quantitative synthesis of the target terminal manganese phosphinidene complex.
  • Detailed structural analysis revealing key bonding features.
  • Experimental and computational evidence elucidating the reaction pathway.

Conclusions:

  • The synthesis provides a stable and accessible route to terminal manganese phosphinidenes.
  • The study advances the understanding of phosphinidene complex chemistry.
  • This complex serves as a platform for further exploration in synthesis and catalysis.