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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.1K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.1K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.6K
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,...
4.6K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.2K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.2K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.0K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.0K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.0K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

11.1K
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.
11.1K

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Updated: Nov 4, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

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Disila- and digermabenzenes.

Takahiro Sasamori1

  • 1Division of Chemistry, Faculty of Pure and Applied Sciences, Tsukuba Research Center for Energy Materials Science (TREMS), University of Tsukuba 1-1-1 Tennodai Tsukuba Ibaraki 305-8571 Japan sasamori@chem.tsukuba.ac.jp.

Chemical Science
|May 27, 2021
PubMed
Summary

Discovered disilabenzene (DSB) and digermabenzene (DGB) compounds exhibit aromaticity similar to benzene but are highly reactive. A 1,2-digermabenzene (DGB) acts as a catalyst for arylalkyne cyclotrimerization.

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Area of Science:

  • Organometallic Chemistry
  • Materials Science
  • Synthetic Chemistry

Background:

  • Disilabenzene (DSB) and digermabenzene (DGB) are analogs of benzene where two carbon atoms are replaced by silicon or germanium.
  • These heterocycles possess significant aromatic character, comparable to benzene.
  • Despite their aromaticity, DSBs and DGBs display high reactivity towards various small molecules.

Purpose of the Study:

  • To summarize recent advancements in the synthesis and reactivity of disilynes and digermynes.
  • To explore the chemical properties and potential applications of disilabenzene (DSB) and digermabenzene (DGB) compounds.
  • To highlight the catalytic activity of 1,2-digermabenzenes (DGBs) in organic transformations.

Main Methods:

  • Synthesis of disilabenzene (DSB) and digermabenzene (DGB) compounds via reactions of disilynes/digermynes with alkynes.
  • Structural and spectroscopic analyses (e.g., NMR, X-ray diffraction) to characterize DSBs and DGBs.
  • Investigation of the reactivity of DSBs and DGBs with small molecules and their catalytic applications.

Main Results:

  • DSBs and DGBs were successfully synthesized and characterized, showing significant aromaticity.
  • These compounds exhibit high reactivity towards oxygen, hydrogen, dienes, and water.
  • A 1,2-digermabenzene (DGB) was identified as an effective catalyst for the cyclotrimerization of arylalkynes, yielding 1,2,4-triarylbenzenes.

Conclusions:

  • DSBs and DGBs represent a unique class of aromatic compounds with tunable reactivity.
  • The catalytic application of 1,2-DGBs in cyclotrimerization opens new synthetic pathways.
  • Further research into DSB and DGB chemistry promises novel materials and catalytic systems.