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Related Concept Videos

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.3K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.3K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.0K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.0K
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

2.1K
Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
2.1K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

29.7K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
29.7K
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...
3.2K

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Updated: Apr 27, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Nazarov-like cyclization reactions.

Martin J Di Grandi1

  • 1Department of Natural Sciences, Fordham University at Lincoln Center, 113 W 60th Street, New York, NY 10023, USA. mdigrandi@fordham.edu.

Organic & Biomolecular Chemistry
|June 21, 2014
PubMed
Summary
This summary is machine-generated.

Recent advancements in Nazarov cyclization chemistry have expanded its utility. New methods now enable the synthesis of cyclopentenones with incorporated heteroatoms and through novel cyclopropane-based approaches.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • The Nazarov cyclization is a key reaction for synthesizing cyclopentenones.
  • It proceeds via a 4π electrocyclization of a 1,4-pentadienyl cation intermediate.
  • Cross-conjugated divinyl ketones are the typical precursors.

Purpose of the Study:

  • To review recent advances in Nazarov cyclization from 2009-2013.
  • To highlight modifications extending the reaction's scope.
  • To cover heteroatom incorporation and cyclopropane-based methods.

Main Methods:

  • Review of literature published between 2009 and 2013.
  • Analysis of modifications to the classical Nazarov cyclization.
  • Focus on heteroatom incorporation and use of cyclopropanes.

Main Results:

  • Recent modifications have significantly broadened the scope of the Nazarov cyclization.
  • The incorporation of heteroatoms into the reaction pathway has been achieved.
  • Cyclopropanes have been successfully employed as double bond equivalents.

Conclusions:

  • The Nazarov cyclization has evolved beyond its original scope.
  • New synthetic strategies allow for greater versatility in cyclopentenone synthesis.
  • Recent developments facilitate both heteroatom- and homo-Nazarov cyclizations.