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

Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

3.4K
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.
3.4K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
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.
3.9K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.2K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
4.2K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

11.9K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
11.9K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

15.9K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
15.9K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K

You might also read

Related Articles

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

Sort by
Same author

Crystal structures of fisetin dihydrate and luteolin monohydrate: crystallization from ethanol-water mixtures.

Acta crystallographica. Section E, Crystallographic communications·2026
Same author

Thionyl Chloride-Mediated Synthesis of Erlenmeyer Azlactones from <i>N</i>-Acylated α-Amino Acids.

The Journal of organic chemistry·2026
Same author

Iron Catalyzed Aryl-Aryl Kumada Cross-Coupling: A Mechanistic and Computational Investigation.

Angewandte Chemie (International ed. in English)·2026
Same author

Characterization of Fused Mn and Cu Corroles and Their Potency as ORR Electrocatalysts.

Inorganic chemistry·2026
Same author

Organocatalytic Deoxygenative Reduction of α,β-Unsaturated Ketones.

Journal of the American Chemical Society·2026
Same author

Catalytic ester hydroboration promoted by actinide complexes featuring six-membered N-heterocyclic imine ligands and actinide-alkoxides activation.

Communications chemistry·2025

Related Experiment Video

Updated: Jul 17, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.6K

The First Planar, Not Twisted, Distannene - A Structural Alkene Analog. Synthesis, Isolation and X-ray

Roman Bashkurov1, Natalia Fridman1, Dmitry Bravo-Zhivotovskii1

  • 1Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, 32000, Israel.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 7, 2023
PubMed
Summary

Researchers synthesized a novel tetrasilyl-substituted distannene with an alkene-like structure. This compound exhibits a planar geometry and a short tin-tin double bond, enabling characteristic alkene reactions.

Keywords:
distannenedouble bondgroup 14 elementsstannylenetin

More Related Videos

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.5K
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

17.2K

Related Experiment Videos

Last Updated: Jul 17, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.6K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.5K
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

17.2K

Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Materials Science

Background:

  • Distannenes, compounds featuring a tin-tin double bond, are relatively rare and often exhibit distorted structures.
  • Understanding the structural and reactive properties of distannenes is crucial for advancing low-valent main group chemistry.

Purpose of the Study:

  • To synthesize and characterize a novel tetrasilyl-substituted distannene.
  • To investigate the structural features and reactivity of the tin-tin double bond in the synthesized compound.
  • To compare the structure of the distannene to that of classical alkenes.

Main Methods:

  • Synthesis of tris(di-tert-butyl-hydridosilyl)stannane (4).
  • Mild thermolysis of compound 4 to yield the target distannene (6).
  • X-ray crystallography to determine the precise molecular structure of compound 6.
  • Reaction studies with carbon tetrachloride and 2,3-dimethylbuta-1,3-diene.

Main Results:

  • Successful synthesis of tetrasilyl-substituted distannene (6) via thermolysis.
  • X-ray crystallography revealed a planar geometry around both tin atoms (Σ∡Sn=359.87°).
  • The compound features a non-twisted Sn=Sn double bond with a length of 2.599 Å, the shortest reported for acyclic distannenes.
  • Compound 6 underwent characteristic reactions, forming a 1,2-dichlorodistannane and a [2+4] cycloadduct.

Conclusions:

  • Compound 6 represents the first distannene with structural properties analogous to a classic alkene.
  • The planar geometry and short Sn=Sn bond contribute to its alkene-like reactivity.
  • This work provides significant insights into the chemistry of low-valent tin compounds.