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Related Concept Videos

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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.
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

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.

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Related Experiment Video

Updated: Jun 25, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Intramolecular phosphine-phosphine donor-acceptor complexes.

Piotr Wawrzyniak1, Amy L Fuller, Alexandra M Z Slawin

  • 1School of Chemistry, EastCHEM, University of St Andrews, St Andrews, Fife KY16 9ST, UK.

Inorganic Chemistry
|February 17, 2009
PubMed
Summary
This summary is machine-generated.

A novel phosphonium-phosphine compound featuring a four-phosphorus chain was synthesized. An intermediate complex, stable in solution, disproportionates upon nucleophile addition, revealing insights into phosphorus chemistry.

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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

Published on: March 20, 2014

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Last Updated: Jun 25, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

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

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

Published on: March 20, 2014

Area of Science:

  • Organophosphorus Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Acenaphthene-based ligands are valuable in catalysis and materials science.
  • Understanding the reactivity of polyphosphorus compounds is crucial for developing new synthetic methodologies.

Purpose of the Study:

  • To investigate the unexpected formation of a polyphosphorus compound from a phosphine precursor.
  • To elucidate the mechanism of this complex transformation.
  • To characterize novel phosphorus-containing compounds.

Main Methods:

  • Synthesis of a novel phosphonium-phosphine compound (13) and a proposed intermediate (14).
  • Crystallographic characterization of compounds 13 and 14.
  • (31)P NMR spectroscopy to study the reaction mechanism and stability of intermediate 14.

Main Results:

  • Unexpected synthesis of a four-phosphorus chain compound (13).
  • Characterization of an intramolecular donor-acceptor complex (14) stable in solid-state and solution.
  • Demonstration of the disproportionation of 14 into 13 and other products upon nucleophilic attack.

Conclusions:

  • The reaction pathway involves a unique polyphosphorus intermediate.
  • Compound 14 exhibits interesting intramolecular interactions and reactivity.
  • This study expands the understanding of phosphorus chain formation and reactivity.