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Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

5.6K
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,...
5.6K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

4.5K
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.
4.5K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

5.2K
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.
5.2K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

3.5K
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.
3.5K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

12.8K
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.
12.8K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

15.7K
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...
15.7K

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Updated: Feb 27, 2026

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

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Highly Bent 1,3-Digerma-2-silaallene.

Tomohiro Sugahara1, Takahiro Sasamori2, Norihiro Tokitoh1

  • 1Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan.

Angewandte Chemie (International Ed. in English)
|July 4, 2017
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel cyclic 1,3-digerma-2-silaallene, a unique organosilicon compound. This bent molecule, isolated as an orange solid, exhibits unusual silicon(0) character due to its ring structure.

Keywords:
digermacyclobutenedigermasilaallenegermaniumsiliconsilylone

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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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

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Area of Science:

  • Organosilicon Chemistry
  • Main Group Chemistry
  • Synthetic Chemistry

Background:

  • 1,3-digerma-2-silaallenes are unsaturated silicon compounds.
  • Cyclic incorporation can significantly alter electronic and structural properties.

Purpose of the Study:

  • To synthesize and characterize a novel cyclic 1,3-digerma-2-silaallene.
  • To investigate the structural and electronic consequences of incorporating this moiety into a five-membered ring.

Main Methods:

  • Chemical synthesis of the target compound.
  • Isolation and characterization of the product as a stable solid.

Main Results:

  • Successful synthesis of a 1,3-digerma-2-silacyclopenta-1,2-diene.
  • The compound was obtained as a stable orange solid.
  • The cyclic framework induces significant bending in the silaallene moiety, leading to silicon(0) character.

Conclusions:

  • Cyclic frameworks can stabilize unusual bonding arrangements in organosilicon compounds.
  • The bent structure is key to the observed silicon(0) character.