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

Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

7.2K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
7.2K

You might also read

Related Articles

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

Sort by
Same author

N─H or O─H Bond Activation With a Bicyclic Si<sub>4</sub> Ring Compound.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Dual Cluster-Surface Click Chemistries on Silver Nanoclusters.

Small science·2026
Same author

Benzylidene insertion reactions in organoplatinum chemistry: mechanism and selectivity.

RSC advances·2026
Same author

Backbone deprotonation defines a hidden decomposition pathway of diphosphine ligands.

Chemical communications (Cambridge, England)·2026
Same author

Combined electrodeposition and electropolymerization method to produce surface-bound polystyrenyl NHC thin films.

Chemical science·2026
Same author

From borane to metal-bound boraindene: a cascade of bond breaking and making at rhodium.

Chemical communications (Cambridge, England)·2026

Related Experiment Video

Updated: Mar 9, 2026

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV
10:42

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV

Published on: December 29, 2016

11.2K

Trapping Rare and Elusive Phosphinidene Chalcogenides.

Cameron M E Graham1, Taylor E Pritchard1, Paul D Boyle1

  • 1Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research, Western University, 1151 Richmond St., London, Ontario, N6A 5B7, Canada.

Angewandte Chemie (International Ed. in English)
|January 11, 2017
PubMed
Summary

New four-membered rings containing phosphorus and chalcogens (sulfur or selenium) were synthesized. These rings serve as precursors to highly reactive phosphinidene chalcogenides, enabling novel chemical transformations.

Keywords:
chalcogensmain group elementsphosphinidene chalcogenidesphosphorusphosphorus chalcogen heterocycles

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

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

Related Experiment Videos

Last Updated: Mar 9, 2026

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV
10:42

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV

Published on: December 29, 2016

11.2K
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

Area of Science:

  • Organophosphorus Chemistry
  • Main Group Chemistry
  • Inorganic Synthesis

Background:

  • Four-membered rings featuring a P2Ch2 core (Ch=S, Se) with phosphorus in the +3 oxidation state are novel synthetic targets.
  • Monomeric phosphinidene chalcogenides (PCh) are highly reactive intermediates that are challenging to isolate and study.
  • Understanding the stability and reactivity of PCh species is crucial for developing new synthetic methodologies.

Purpose of the Study:

  • To synthesize novel four-membered rings with a P2Ch2 core.
  • To investigate the utility of these rings as precursors for monomeric phosphinidene chalcogenides.
  • To elucidate the reactivity and stability of phosphinidene sulfides and selenides.

Main Methods:

  • Synthesis of four-membered P2Ch2 rings.
  • Reaction of P2Ch2 rings with N-heterocyclic carbenes to generate phosphinidene sulfides.
  • Cycloaddition reactions of phosphinidene selenides with dienes at elevated temperatures.
  • Computational studies to understand reaction mechanisms and stability.

Main Results:

  • Successful synthesis of four-membered P2Ch2 rings (Ch=S, Se) with phosphorus in the +3 oxidation state.
  • Demonstration that N-heterocyclic carbenes can abstract a chalcogen atom, yielding base-stabilized phosphinidene sulfides.
  • Evidence for the persistence of phosphinidene selenides in solution, shown by cycloaddition reactions.
  • Computational analysis provided insights into the conditions favoring the liberation of phosphinidene chalcogenides.

Conclusions:

  • The synthesized P2Ch2 rings are effective precursors for generating monomeric phosphinidene chalcogenides.
  • Base-stabilized phosphinidene sulfides and persistent phosphinidene selenides can be accessed from these ring systems.
  • Computational chemistry plays a vital role in understanding the reactivity and stability of these transient species.