Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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

[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.

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

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.

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

Stability of Conjugated Dienes

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.

You might also read

Related Articles

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

Sort by

Same author

Smallest acyclic tricationic molecule containing a Bis(phosphine)-stabilized low-valent triantimony-based Unit.

Nature communications·2026

Same author

Catalytic Asymmetric Ionic Hydrogenation of α-Alkyl Styrenes.

Journal of the American Chemical Society·2025

Same author

An intramolecular phosphine-oxide stabilized germanium(IV) di-cation with enhanced Lewis acidity and catalytic applications.

Chemical communications (Cambridge, England)·2025

Same author

Tetra-Cationic Distibane Stabilized by Bis(α-iminopyridine) and Its Reactivity.

Journal of the American Chemical Society·2025

Same author

Reactivity Study of the Bis(phosphine)-Stabilized Antimony(I) Cation.

Inorganic chemistry·2024

Same author

Diverse Functionality of Molecular Germanium: Emerging Opportunities as Catalysts.

Journal of the American Chemical Society·2024

Same journal

Solvent Coordination-Induced Synergistic Phase, Facet, and Defect Engineering of CdS for Photocatalytic Hydrogen Evolution.

Inorganic chemistry·2026

Same journal

Tailoring the Electron-Enriched Microenvironment of UiO-66 via Thiol Functionalization to Boost Non-Thermal Plasma CO<sub>2</sub> Conversion.

Inorganic chemistry·2026

Same journal

Nonporous Self-Assembled Pd(II) Coordination Cage Enabling Dual Capture of Iodine and Methyl Iodide.

Inorganic chemistry·2026

Same journal

A Three-Dimensional Organic-Inorganic Hybrid Perovskite-Type Molecular Ferroelectric Material [3.2.2-H<sub>2</sub>dabcn]Rb(NO<sub>3</sub>)<sub>3</sub>.

Inorganic chemistry·2026

Same journal

Nonlinear Optical-Active NaAlP<sub>2</sub>S<sub>6</sub> Synthesized by the MOBQ Method: Synthesis, Structure, and Optical Properties.

Inorganic chemistry·2026

Same journal

Ligand-Controlled Redox and Photophysical Properties in Photoluminescent Tris-Heteroleptic Ru(II) Pyridyl-Phosphonium Ylide Complexes.

Inorganic chemistry·2026

See all related articles

Search research articles

Related Experiment Video

Updated: Mar 21, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Butadiene-Based Multidentate Ligand Formation via Stannylene Assisted C-C Coupling.

Niranjan Patel¹, Ravindra K Raut¹, Cem B Yildiz²

¹Department of Chemistry, Indian Institute of Science Education and Research, Pune, Dr. Homi Bhabha Road, Pashan, Pune 411008, Maharashtra, India.

Inorganic Chemistry

|March 19, 2026

Summary

This summary is machine-generated.

New redox-active bis(α-iminopyridine) ligands reacted with a tin precursor to form bisstannylene compounds. These compounds undergo C-C coupling, yielding butadiene units and new multifunctionalized ligands after demetalation.

More Related Videos

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

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

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

Published on: March 20, 2014

Related Experiment Videos

Last Updated: Mar 21, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

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

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

Published on: March 20, 2014

Area of Science:

Organometallic Chemistry
Ligand Design
Tin Chemistry

Background:

Redox-active ligands are crucial for tuning metal center reactivity.
Bis(α-iminopyridine) ligands offer unique coordination environments.
Tin(II) compounds are versatile precursors for novel organotin species.

Purpose of the Study:

To synthesize and characterize novel bisstannylene compounds derived from redox-active bis(α-iminopyridine) ligands.
To investigate the C-C coupling reactions of these bisstannylene compounds.
To explore the formation of new multifunctionalized ligands through demetalation.

Main Methods:

Reaction of bis(α-iminopyridine) ligands with Sn[N(SiMe3)2]2.
In situ NMR spectroscopy for intermediate detection.
Single crystal X-ray diffraction (SCXRD) for structural characterization.
NMR, mass spectrometry, and absorbance spectroscopy for compound analysis.
Density Functional Theory (DFT) calculations.

Main Results:

Synthesis of bisstannylene compounds 1 and 2 via intermolecular and intramolecular C-C coupling, respectively.
Characterization of ene-amide stabilized bisstannylene intermediates (I1, I2) and a monostannylene.
Formation of oxidized compounds 3 and 4, and bisstannylene 5.
Generation of new multifunctionalized ligands L3 and L4 via demetalation.

Conclusions:

Redox-active bis(α-iminopyridine) ligands facilitate the formation of unique bisstannylene compounds.
C-C coupling reactions lead to the incorporation of butadiene units into the ligand backbone.
The study demonstrates a pathway to novel organotin compounds and valuable multifunctionalized ligands.