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

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.2K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.2K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.1K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
16.1K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.6K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.6K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.4K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.4K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.8K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.8K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.3K
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...
8.3K

You might also read

Related Articles

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

Sort by
Same author

CAV1-dependent mitochondrial transfer from hucMSCs reprograms epithelial lipid metabolism to relieve pulmonary fibrosis.

Stem cell research & therapy·2026
Same author

Preparations reduce drivers' perceived risk when resuming control from conditionally automated vehicles.

Traffic injury prevention·2026
Same author

Chalcogen···π Bonding Catalysis: Concept, Reaction Development and Emerging Opportunities.

Chemistry, an Asian journal·2026
Same author

Gestational diabetes mellitus (GDM) in the first-reported pregnancy modifies association between interpregnancy-weight-change and GDM risk in the subsequent pregnancy.

AJOG global reports·2026
Same author

EGFR S442 ectodomain mutation confers cetuximab resistance that can be overcome by ERBB2 blockade with trastuzumab-deruxtecan.

Cancer letters·2026
Same author

Four-dimensional CTA detects non-puncture hemorrhage after percutaneous transluminal angioplasty for peripheral arterial disease.

Quantitative imaging in medicine and surgery·2026

Related Experiment Video

Updated: Aug 9, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K

Chalcogen Bonding Catalysis of the Cloke-Wilson Rearrangement.

Xinglong Yuan1, Lintao Bao1, Zhiguo Zhao1

  • 1School of Chemistry and Chemical Engineering Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, Jinan, 250100, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 17, 2023
PubMed
Summary

Researchers developed a novel weak interaction catalysis for the Cloke-Wilson rearrangement using double Se⋅⋅⋅O interactions. This method efficiently synthesizes dihydrofurans, offering a new strategy for heterocycle construction.

Keywords:
Cloke-Wilson rearrangementSe⋅⋅⋅O bondingchalcogen bondingcyclopropanessupramolecular catalysis

More Related Videos

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

9.3K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

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

Published on: March 20, 2014

25.5K

Related Experiment Videos

Last Updated: Aug 9, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K
Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

9.3K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

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

Published on: March 20, 2014

25.5K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Heterocyclic Chemistry

Background:

  • The Cloke-Wilson rearrangement is a key reaction for synthesizing heterocycles.
  • Conventional methods rely on harsh catalysts like strong Lewis acids, Brønsted acids, and Lewis bases.
  • Developing weak interaction catalysis for this reaction remains an unexplored challenge.

Purpose of the Study:

  • To introduce a novel weak interaction catalysis for the Cloke-Wilson rearrangement.
  • To explore the use of chalcogen bonding for activating carbonyl cyclopropanes.
  • To establish an alternative and milder strategy for dihydrofuran synthesis.

Main Methods:

  • Utilizing a chalcogen bonding catalysis approach.
  • Employing double Se⋅⋅⋅O interactions for the activation of carbonyl cyclopropanes.
  • Investigating the synthesis of various dihydrofuran derivatives.

Main Results:

  • Successfully achieved the Cloke-Wilson rearrangement via chalcogen bonding catalysis.
  • Demonstrated activation of carbonyl cyclopropanes through double Se⋅⋅⋅O interactions.
  • Obtained a diverse range of dihydrofurans in good yields.

Conclusions:

  • A novel chalcogen bonding catalysis method for the Cloke-Wilson rearrangement has been established.
  • This approach provides an effective alternative to traditional catalytic systems.
  • The method offers a new pathway for the efficient synthesis of dihydrofurans.