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Related Concept Videos

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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.
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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.
[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.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

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 more stable, the...
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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 stereochemistry.

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Related Experiment Video

Updated: May 11, 2026

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
11:42

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

Selective functionalization of a bis-silylene.

Rajendra S Ghadwal1, Ramachandran Azhakar, Kevin Pröpper

  • 1Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany. rghadwal@uni-goettingen.de

Chemical Communications (Cambridge, England)
|May 30, 2013
PubMed
Summary
This summary is machine-generated.

Researchers selectively functionalized a four-membered N-heterocyclic bis-silylene using oxygen sources. This study reports the first four-membered mono-silylene featuring a di-coordinate silicon atom.

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

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Last Updated: May 11, 2026

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Area of Science:

  • Organosilicon Chemistry
  • N-heterocyclic Carbene Chemistry

Background:

  • Functionalization of N-heterocyclic carbenes (NHCs) significantly impacts their stability and electronic properties.
  • Understanding the reactivity of silylenes is crucial for developing novel silicon-based compounds.

Purpose of the Study:

  • To investigate the selective functionalization of a four-membered N-heterocyclic bis-silylene.
  • To explore the reactions of bis-silylene (2,6-Ar2C6H3NSi:)2 with mono-oxygen sources.

Main Methods:

  • Reaction of the four-membered N-heterocyclic bis-silylene with nitrous oxide (N2O) and trimethylamine N-oxide (Me3NO).
  • Characterization of reaction products using spectroscopic techniques.

Main Results:

  • Selective mono-oxygenation of the bis-silylene with N2O yielded the mono-silylene (2,6-Ar2C6H3NSi(OH)2)(2,6-Ar2C6H3NSi:) as the major product.
  • A small amount of the fully oxidized product (2,6-Ar2C6H3NSi(OH)2)2 was also observed.
  • The major product represents the first example of a four-membered mono-silylene with a di-coordinate silicon atom.

Conclusions:

  • The study demonstrates a selective functionalization pathway for four-membered N-heterocyclic bis-silylenes.
  • The formation of a novel di-coordinate silicon species expands the scope of silylene chemistry.