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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
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.
3.7K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.1K
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.
5.1K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

13.7K
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.
13.7K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

4.3K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
4.3K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.7K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.7K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

6.5K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
6.5K

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Temperature-Dependent Double Isocyanide Insertion Reaction To Construct a Polycyclic Skeleton.

Yaming Tian1, Lumin Tian1, Chunju Li1

  • 1Department of Chemistry, Innovative Drug Research Center, Shanghai University , 99 Shangda Road, Shanghai 200444, China.

Organic Letters
|February 11, 2016
PubMed
Summary

Researchers developed a new method for double isocyanide insertion using potassium tetrachloroaurate(III). This efficient strategy quickly builds complex polycyclic structures, with unexpected oxygen migration noted at lower temperatures.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Isocyanides are versatile building blocks in organic synthesis.
  • Developing efficient methods for complex molecule construction is crucial.
  • Gold catalysis offers unique reactivity for C-C bond formation.

Purpose of the Study:

  • To introduce a novel strategy for selective double insertion of isocyanides.
  • To efficiently synthesize complex polycyclic skeletons.
  • To investigate the reaction mechanism and potential side reactions.

Main Methods:

  • Utilizing potassium tetrachloroaurate(III) as a catalyst.
  • Employing isocyanides as substrates for double insertion reactions.
  • Conducting reactions under varying temperature conditions to observe effects.

Main Results:

  • A novel strategy for selective double isocyanide insertion was successfully developed.
  • The method provides efficient access to complex polycyclic frameworks.
  • An unexpected oxygen migration was observed at lower reaction temperatures, suggesting a complex reaction pathway.

Conclusions:

  • The developed gold-catalyzed strategy offers an efficient route to complex polycyclic compounds.
  • The observation of oxygen migration provides insights into the reaction mechanism.
  • This methodology expands the synthetic utility of isocyanides in constructing intricate molecular architectures.