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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.5K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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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...
3.5K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.2K
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.
3.2K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

2.3K
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...
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Ziegler–Natta Chain-Growth Polymerization: Overview01:17

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3.8K
Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
3.8K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.5K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Reactive & Efficient: Organic Azides as Cross-Linkers in Material Sciences.

Marvin Schock1, Stefan Bräse1,2,3

  • 1Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.

Molecules (Basel, Switzerland)
|February 28, 2020
PubMed
Summary

Organic azides are versatile compounds used in materials science. Their ability to release nitrogen and form reactive nitrenes enables efficient polymer crosslinking for advanced devices and energetic materials.

Keywords:
azidesnitrenesphotochemistrypolymersthermosets

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Area of Science:

  • Organic Chemistry
  • Material Science
  • Polymer Science

Background:

  • Organic azides exhibit exceptional reactivity, making them valuable in chemistry and material sciences.
  • Key reactions include the Huisgen cycloaddition, Staudinger reduction, aza-Wittig reaction, and Curtius rearrangement.
  • Their propensity to release nitrogen upon thermal or photolytic activation is crucial for energetic materials and nitrene generation.

Purpose of the Study:

  • This review focuses on the nitrene-based applications of multivalent organic azides.
  • It highlights their use in material and life sciences.
  • The review explores how these compounds can alter polymer properties and enhance device efficiencies.

Main Methods:

  • The review synthesizes information on organic azide reactivity and applications.
  • It specifically examines nitrene generation from multivalent organic azides.
  • Applications in polymer crosslinking for various devices are discussed.

Main Results:

  • Multivalent organic azides are effective in generating reactive nitrenes.
  • Nitrene-mediated polymer crosslinking significantly alters polymer physical properties.
  • These applications enhance the performance of devices like organic solar cells and LEDs.

Conclusions:

  • Nitrene-based applications of multivalent organic azides offer significant potential in material and life sciences.
  • Their use in polymer crosslinking leads to improved material properties and device efficiencies.
  • Organic azides are key components for developing advanced energetic materials and functional polymers.