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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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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.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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2.1K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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3.0K
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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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Cyaphide-Azide 1,3-Dipolar Cycloaddition Reactions: Scope and Applicability.

Eric S Yang1, Alex Mapp1, Andrew Taylor1

  • 1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Rd., Oxford, OX1 3TA, U.K.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 20, 2023
PubMed
Summary

A novel cyaphide-azide cycloaddition reaction creates metallo-triazaphospholes, including gold, magnesium, and germanium complexes. These compounds serve as versatile precursors for further functionalization.

Keywords:
azideclick chemistrycyaphidephosphorustriazaphospholes

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Chemistry

Background:

  • The cyaphide-azide 1,3-dipolar cycloaddition is a key reaction in heterocyclic synthesis.
  • Metallo-triazaphospholes are an emerging class of organometallic compounds with potential applications.

Purpose of the Study:

  • To report new examples of the cyaphide-azide 1,3-dipolar cycloaddition reaction.
  • To synthesize novel gold(I), magnesium(II), and germanium(II) metallo-triazaphospholes.
  • To explore the utility of these metallo-triazaphospholes as precursors for carbon-functionalized species.

Main Methods:

  • The study employed the cyaphide-azide 1,3-dipolar cycloaddition reaction.
  • Synthesis of gold(I), magnesium(II), and germanium(II) metallo-triazaphospholes under mild conditions.
  • Extension of the reaction to difunctional azide compounds like 1,3-diazidobenzene.

Main Results:

  • Several gold(I), magnesium(II), and germanium(II) metallo-triazaphospholes were synthesized in good yields.
  • The reaction proceeds efficiently under mild conditions, similar to the 'click' reaction but without a catalyst.
  • The synthesized metallo-triazaphospholes were successfully converted into carbon-functionalized derivatives, including protio- and iodo-triazaphospholes.

Conclusions:

  • The cyaphide-azide cycloaddition provides a straightforward route to diverse metallo-triazaphospholes.
  • These metallo-triazaphospholes are valuable synthetic intermediates for accessing novel organometallic compounds.
  • The methodology offers a catalytic-free approach, enhancing its practicality in synthetic chemistry.