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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.9K
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

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.7K
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.
3.7K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.9K
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.
10.9K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
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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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.4K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.4K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.0K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
2.0K

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Transition metal catalyzed [6 + 2] cycloadditions.

Amit Anand1, Prabhpreet Singh2, Vipan Kumar2

  • 1Department of Chemistry, Khalsa College Amritsar 143005 Punjab India aa_wiz@yahoo.com.

RSC Advances
|May 9, 2022
PubMed
Summary
This summary is machine-generated.

Transition metal-catalyzed [6 + 2] cycloaddition reactions offer a key synthetic route to eight-membered rings. This review details catalysts and substrates for constructing complex carbo- and heterocyclic systems.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Cycloaddition reactions are fundamental in organic synthesis.
  • Eight-membered carbocyclic and heterocyclic systems are valuable structural motifs.
  • Efficient methods for constructing these rings are highly sought after.

Purpose of the Study:

  • To provide an updated review of transition metal-catalyzed [6 + 2] cycloaddition reactions.
  • To highlight the scope of 6π-electron contributing substrates.
  • To showcase the utility of various metal catalysts in these transformations.

Main Methods:

  • Review of literature on transition metal-catalyzed [6 + 2] cycloadditions.
  • Focus on reactions involving cycloheptatrienes, cyclooctatetrenes, allenals, vinylcyclobutanones, and fulvenes.
  • Discussion of catalysts including rhodium, cobalt, titanium, copper, platinum, ruthenium, rhenium, and diphenylprolinolsilyl ethers.

Main Results:

  • Transition metal catalysis enables the formation of eight-membered rings via [6 + 2] cycloadditions.
  • A diverse range of functionalized substrates can be employed.
  • Access to various condensed carbo- and heterocyclic systems is achieved.

Conclusions:

  • Transition metal-catalyzed [6 + 2] cycloaddition reactions are versatile for synthesizing eight-membered rings.
  • These reactions provide efficient pathways to complex cyclic molecules.
  • The review summarizes recent advancements in this field.