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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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

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

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.
Introduction to Functional Groups02:08

Introduction to Functional Groups


Functional groups are group of atoms with specific chemical properties that occur within organic molecules and sometimes denoted as “R”. Functional groups are found along the carbon backbone of macromolecules can form chains or rings of carbon atoms. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
Types of common functional groups
The table below summarizes some of the major functional groups in organic chemistry. (The...
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Calix[4]tubes: an approach to functionalization.

Kirill Puchnin1, Pavel Zaikin, Dmitry Cheshkov

  • 1Department of Chemistry, M V Lomonosov Moscow State University, Moscow, Russia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 19, 2012
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel calix[4]tubes with adamantyl units. These functionalized tubes act as anion receptors and enhance potassium uptake, showcasing versatile host properties.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Host-Guest Chemistry

Background:

  • Calix[4]arenes are macrocyclic compounds known for their host-guest properties.
  • Functionalization of calixarene scaffolds is crucial for tailoring their binding capabilities.
  • Adamantyl groups can influence the steric and electronic properties of macrocycles.

Purpose of the Study:

  • To synthesize novel calix[4]tube derivatives functionalized with adamantyl units.
  • To explore the chemical transformations of these calix[4]tubes.
  • To investigate the anion-binding and ion-transport properties of the synthesized compounds.

Main Methods:

  • Preparation of adamantylcalix[4]arenes with ester groups and tetratosylates.
  • Chemical modification of calix[4]tubes to introduce various functional groups (ester, acid, hydroxy, amine, urea).
  • Characterization of the synthesized calix[4]tube derivatives.

Main Results:

  • A series of calix[4]tubes bearing multiple 3-methoxycarbonyl- and 3-methoxycarbonylmethyl-1-adamantyl units were synthesized in good yield.
  • Diverse functionalized calix[4]tubes, including ester-, acid-, hydroxy-, amine-, and urea-derivatives, were obtained through further transformations.
  • Introduction of urea groups resulted in potent anion-targeted receptors with heteroditopic binding capabilities, complementing existing potassium-uptake properties.

Conclusions:

  • Novel functionalized calix[4]tubes with adamantyl substituents were successfully synthesized.
  • The synthesized calix[4]tubes exhibit promising anion recognition and ion transport functionalities.
  • These findings expand the scope of calix[4]tube applications in supramolecular chemistry and sensing.