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

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

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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.
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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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,...
2.9K
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

2.6K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred...
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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Truce-Smiles Rearrangement Cascade Enables Synthesis of Pyrazoline Derivatives.

Dengyuan Gao1, Jiacheng Deng2, Zhenguang Guo1

  • 1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua, Zhejiang 321004, P. R. China.

Organic Letters
|March 9, 2026
PubMed
Summary
This summary is machine-generated.

A novel five-bond cascade reaction synthesizes diverse pyrazoline derivatives using N-(arylsulfonyl) acrylamides and Huisgen zwitterions. This efficient method offers scalability and structural variety for pyrazoline synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Pyrazoline derivatives are important heterocyclic compounds with diverse biological activities.
  • Efficient synthetic methods for constructing pyrazolines are crucial for drug discovery and materials science.

Purpose of the Study:

  • To develop a novel cascade reaction for the efficient synthesis of pyrazoline derivatives.
  • To explore the incorporation of Huisgen zwitterions into a Truce-Smiles cascade for one-step five-bond construction.

Main Methods:

  • The reaction involves N-(arylsulfonyl) acrylamides and in situ generated Huisgen zwitterions (from azodicarboxylates and triphenylphosphine).
  • The transformation proceeds via a conjugate addition-Smiles rearrangement-cyclization sequence under mild, base-free conditions.

Main Results:

  • Diverse pyrazoline derivatives were synthesized in moderate to excellent yields.
  • This represents the first use of Huisgen zwitterions in a Truce-Smiles cascade.
  • The reaction demonstrated scalability and potential for structural diversification.

Conclusions:

  • A novel and efficient five-bond-forming cascade reaction for pyrazoline synthesis has been established.
  • The methodology offers a scalable and versatile approach for accessing diverse pyrazoline structures.
  • This work expands the utility of Huisgen zwitterions in complex cascade reactions.