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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
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.
2.5K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.5K
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.
3.5K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.0K
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.
2.0K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.1K
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.
10.1K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

9.3K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
9.3K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.0K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.0K

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Mechanistical Study on Substrate-Controlled Highly Selective [2+2] and [2+3] Cycloaddition Reactions.

Junbo Wang1, Chuan Deng1, Yong Zhang2

  • 1School of Physics and Information Technology, Shaanxi Normal University, Xi'an, 710119, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 29, 2024
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Summary

Researchers achieved selective synthesis of four- and five-membered carbon rings on metal surfaces using a single precursor. This breakthrough in polycyclic hydrocarbon synthesis offers new possibilities for electronic devices.

Keywords:
cycloaddition reactionsdensity functional theoryon-surface synthesisorganometallic intermediate statesscanning tunneling microscopy

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Surface Science

Background:

  • Polycyclic conjugated hydrocarbons are crucial for electronic devices.
  • Synthesizing specific carbon ring sizes (four- and five-membered) on metal surfaces is challenging due to multiple reaction pathways.

Purpose of the Study:

  • To achieve substrate-controlled, highly selective synthesis of four- and five-membered carbon rings from a single precursor.
  • To explore the mechanism behind this novel surface-directed reaction selectivity.

Main Methods:

  • Utilizing a single precursor molecule for cycloaddition reactions.
  • Employing gold (Au(111)) and silver (Ag(111)) metal surfaces as substrates.
  • Characterizing reaction products using bond-resolving scanning tunneling microscopy (BR-STM) with a CO-functionalized tip.
  • Performing density functional theory (DFT) calculations to elucidate reaction mechanisms.

Main Results:

  • Achieved a 97% yield of four-membered carbon rings on Au(111).
  • Achieved a 96% yield of five-membered carbon rings on Ag(111).
  • Successfully determined the topological structures of the synthesized products.
  • Elucidated the mechanism of substrate-controlled reaction selectivity.

Conclusions:

  • Demonstrated a novel method for highly selective synthesis of four- and five-membered carbon rings.
  • The findings pave the way for controlled synthesis of polycyclic conjugated hydrocarbons with non-benzenoid rings.
  • This approach offers potential for designing advanced materials for electronic applications.