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

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
[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.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

You might also read

Related Articles

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

Sort by
Same author

Leukemia Cutis at Initial Diagnosis of Acute Myeloid Leukemia Consistent With Therapy-Related Disease After Lung Cancer Chemotherapy: A Case Report.

Case reports in hematology·2026
Same author

Progress towards the elimination of vertical transmission of HIV, syphilis and hepatitis B in 21 high-burden countries.

Journal of the International AIDS Society·2026
Same author

Rhenium Chalcogenide Clusters Containing <i>para</i>-Substituted Phenylacetylide Ligands: Synthesis, Characterization, and Investigation of Substituent Effects on Spectroscopic and Electrochemical Properties.

Organometallics·2025
Same author

Right ventricular injury during VV-ECMO for severe ARDS: Does time matter?

Journal of the Intensive Care Society·2025
Same author

State Child Abuse and Mandated Reporting Policies for Prenatal Substance Use and Congenital Syphilis Case Rates: United States, 2018-2022.

American journal of public health·2025
Same author

Reported Neurologic Manifestations Among Persons With Syphilis by Stage of Infection-12 States, 2019-2022.

Clinical infectious diseases : an official publication of the Infectious Diseases Society of America·2025
Same journal

Ligand non-innocence enables HAT at dinuclear nickel complexes.

Dalton transactions (Cambridge, England : 2003)·2026
Same journal

Preservation of the 2<i>H</i>-MoS<sub>2</sub> structure in intercalation compounds with bulky cations.

Dalton transactions (Cambridge, England : 2003)·2026
Same journal

A "one-stone-two-birds" strategy for enhancing the quantum yield and designing dual-emission AIE MOFs.

Dalton transactions (Cambridge, England : 2003)·2026
Same journal

Scalable synthesis of highly crystalline 2D bimetallic MOFs on GO as electrode materials for alkaline zinc batteries.

Dalton transactions (Cambridge, England : 2003)·2026
Same journal

Catalytic surface degradation of (CF<sub>2</sub>H)<sub>2</sub>O to CF<sub>3</sub>H at a Si-teflate doped aluminium chlorofluoride Lewis superacid.

Dalton transactions (Cambridge, England : 2003)·2026
Same journal

A molecular 'LEGO®' approach to high-spin triangular {Mn<sup>III</sup>Ln<sub>2</sub>} clusters from {Mn<sup>III</sup>} and {Ln<sub>2</sub>} metalloligands.

Dalton transactions (Cambridge, England : 2003)·2026
See all related articles

Related Experiment Video

Updated: May 12, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Azide alkyne cycloaddition facilitated by hexanuclear rhenium chalcogenide cluster complexes.

Stanley A Knott1, Jeffrey N Templeton, Jessica L Durham

  • 1Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USA.

Dalton Transactions (Cambridge, England : 2003)
|April 16, 2013
PubMed
Summary
This summary is machine-generated.

New hexanuclear rhenium clusters with azide ligands were synthesized and reacted with alkynes to form triazolate complexes. These rhenium clusters facilitate heterocyclic ring formation from azide moieties.

More Related Videos

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Related Experiment Videos

Last Updated: May 12, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Hexanuclear rhenium clusters are of interest due to their unique electronic and structural properties.
  • Azide ligands can participate in various chemical transformations, including cycloaddition reactions.

Purpose of the Study:

  • To synthesize and characterize novel hexanuclear rhenium clusters containing azide ligands.
  • To investigate the reactivity of these rhenium-azide clusters with activated alkynes.
  • To explore the formation of triazolate complexes and heterocyclic ring systems.

Main Methods:

  • Synthesis of rhenium-azide clusters from pyridine precursors.
  • Reaction of rhenium clusters with activated alkynes (dimethyl acetylenedicarboxylate and methyl 4-hydroxyhex-2-yneoate).
  • Structural characterization using single-crystal X-ray diffraction analysis.
  • Alkylation studies of the resulting triazolate complexes.

Main Results:

  • Successful synthesis and full characterization of two hexanuclear rhenium clusters: [Re6Se8(PEt3)5(N3)]BF4 and [Re6Se8(PEt3)4(N3)2].
  • Reaction of [Re6Se8(PEt3)5(N3)]BF4 with activated alkynes yielded triazolate cluster complexes [Re6Se8(PEt3)5(L1 or L2)]BF4.
  • Preparation of a bis-triazolato complex, cis-[Re6Se8(PEt3)4(L1)2], from the corresponding bis-azido precursor, demonstrating double heterocyclic ring formation.
  • Structural elucidation of key complexes via X-ray diffraction.
  • Reported alkylation of [Re6Se8(PEt3)5(L1)]BF4 with benzyl bromide and methyl iodide.

Conclusions:

  • Hexanuclear rhenium clusters containing azide ligands can be effectively synthesized and characterized.
  • These rhenium clusters are capable of promoting the formation of triazolate complexes through reactions with activated alkynes.
  • The study demonstrates the potential of these rhenium clusters in facilitating heterocyclic ring formation involving azide moieties.
  • Further functionalization of the triazolate complexes through alkylation is feasible.