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Related Concept Videos

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...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.0K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.7K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.7K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.2K
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...
4.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.2K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.2K
E1 Reaction: Stereochemistry and Regiochemistry02:43

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10.4K
One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. In the example discussed, the presence of water as a weak base favors elimination over substitution to generate two alkenes. Given that alkenes’ stability increases with the number of alkyl groups across the double bond, typically, E1 reactions lead to the Zaitsev product, for this is more substituted and stable than the Hofmann product.
10.4K

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Active Ester Functionalized Azobenzenes as Versatile Building Blocks.

Sven Schultzke1,2, Melanie Walther1,2, Anne Staubitz1,2

  • 1Institute for Analytical and Organic Chemistry, University of Bremen, Leobener Straße 7, D-28359 Bremen, Germany.

Molecules (Basel, Switzerland)
|July 2, 2021
PubMed
Summary
This summary is machine-generated.

A new palladium-catalyzed method enables efficient functionalization of azobenzenes with NHS esters. These modified azobenzenes readily react with primary amines, expanding their utility in biology and materials science.

Keywords:
N-hydroxysuccinimideazobenzenechemical biologydiazocinemolecular switchespalladium-catalyzed carbonylationphoto-switchable NHS ester

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Area of Science:

  • Organic Chemistry
  • Molecular Switches
  • Catalysis

Background:

  • Azobenzenes are valuable molecular switches.
  • Selective functionalization of azobenzenes remains challenging.

Purpose of the Study:

  • To develop a high-yielding method for introducing NHS esters to azobenzenes and diazocines.
  • To enable efficient post-functionalization of azobenzenes.

Main Methods:

  • Palladium-catalyzed cross-coupling reaction.
  • Mild reaction conditions.
  • Introduction of N-hydroxysuccinimide (NHS) esters.

Main Results:

  • Consistently high yields achieved for NHS ester introduction.
  • NHS-functionalized azobenzenes react quantitatively with primary amines.
  • Demonstrated applicability to azobenzenes and diazocines.

Conclusions:

  • Established a robust method for selective azobenzene functionalization.
  • The developed method facilitates the conjugation of azobenzenes with biologically and materially relevant amines.
  • Enhanced utility of azobenzenes in diverse applications.