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

Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

10.7K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
10.7K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

9.3K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
9.3K
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

5.4K
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...
5.4K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

3.3K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
3.3K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

7.7K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
7.7K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.9K
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.
4.9K

You might also read

Related Articles

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

Sort by
Same author

Developing selective access to P(V)/(V) and a heteroatom-bridged P(III)P(V) 1,4-diphosphabarrelene(s) using a 1,4-diphosphinine.

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

Unexpected bonding ambiguity of the open/closed-shell R<sub>2</sub>PO ligand family: the case of phosphinoyl <i>vs.</i> phosphoryl if bound to transition metals in their low oxidation state.

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

1,4-Phosphagermines: An Anionic 6π-heteroaromatic Biradicaloid and a Persistent π-Delocalized Radical.

Inorganic chemistry·2025
Same author

A "phosphorus derivative" of aziridines: on the importance of ring strain energy and three heteropolar bonds in azaphosphiridines.

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

Oxaphosphiranes: isolable phosphorus-containing epoxide rings.

Dalton transactions (Cambridge, England : 2003)·2024
Same author

Synthesis of P-bridged, planar bis(NHC) BCl<sub>3</sub> adducts.

Dalton transactions (Cambridge, England : 2003)·2024

Related Experiment Video

Updated: Mar 7, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

8.9K

Ring opening of a sterically crowded 1,2-oxaphosphetane complex.

A W Kyri1, P Brehm1, G Schnakenburg1

  • 1Institut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany. r.streubel@uni-bonn.de.

Dalton Transactions (Cambridge, England : 2003)
|February 15, 2017
PubMed
Summary

This study reports the first ring opening of a 1,2-oxaphosphetane complex using water, yielding a phosphinito complex. This complex was then used in ring-forming reactions with silicon and germanium compounds.

More Related Videos

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.4K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.4K

Related Experiment Videos

Last Updated: Mar 7, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

8.9K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.4K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.4K

Area of Science:

  • Organophosphorus Chemistry
  • Organometallic Chemistry
  • Synthetic Organic Chemistry

Background:

  • 1,2-oxaphosphetanes are four-membered rings containing phosphorus and oxygen.
  • Their ring opening reactions are important for synthesizing various organophosphorus compounds.
  • Limited examples of 1,2-oxaphosphetane complex ring opening exist.

Purpose of the Study:

  • To report the first ring opening reaction of a 1,2-oxaphosphetane complex.
  • To synthesize a C-OH functional phosphinito complex.
  • To explore the utility of the synthesized phosphinito complex in subsequent ring-forming reactions.

Main Methods:

  • Reaction of a 1,2-oxaphosphetane complex with water in the presence of [Li(12-crown-4)]Cl.
  • Isolation and characterization of the resulting phosphinito complex.
  • Subsequent reactions of the phosphinito complex with Me2ECl2 (E = Si, Ge) and various nitrogen bases.

Main Results:

  • The first example of a water-induced ring opening of a 1,2-oxaphosphetane complex was achieved.
  • A novel C-OH functional phosphinito complex was successfully synthesized.
  • The phosphinito complex demonstrated reactivity in ring-forming reactions with silicon and germanium precursors.

Conclusions:

  • The study establishes a new synthetic route involving 1,2-oxaphosphetane ring opening.
  • The synthesized phosphinito complex serves as a versatile intermediate for constructing new organophosphorus compounds.
  • This work expands the known reactivity of 1,2-oxaphosphetane complexes in synthetic chemistry.