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Properties of Organometallic Compounds

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

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.

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

[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.

Pericyclic Reactions: Introduction

Pericyclic Reactions: Introduction

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...

Cycloaddition Reactions: Overview

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.

Frost Circles for Different Conjugated Systems

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.

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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

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Published on: October 15, 2019

Engineering organic macrocycles and cages: versatile bonding approaches.

Sheng-Li Huang¹, Guo-Xin Jin, He-Kuan Luo

¹Institute of Materials Research and Engineering, Agency for Science, Technology and Research, 3 Research Link, Singapore 117602 (Singapore).

Chemistry, an Asian Journal

|November 19, 2014

Summary

Purely organic macrocycles and cages are emerging as versatile soft materials. These structures, built with various bonding strategies, offer advantages over metal-based assemblies for applications like gas storage and catalysis.

Keywords:

cage compounds discrete compound macrocycles soft material supramolecular chemistry

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Area of Science:

Supramolecular Chemistry
Materials Science

Background:

Supramolecular chemistry has yielded numerous functional macrocycles and cages, predominantly metal coordination networks.
Purely organic assemblies are less explored but offer significant advantages.

Purpose of the Study:

To highlight versatile bonding approaches for engineering organic macrocycles and cages.
To showcase emerging applications of these organic soft materials.

Main Methods:

Review of different covalent bonding strategies (reversible and irreversible) for constructing organic supramolecular structures.
Analysis of the properties and applications of engineered organic macrocycles and cages.

Main Results:

Organic macrocycles and cages demonstrate chemical robustness and good processability in organic solvents.
These materials are suitable for pilot-scale production and diverse applications.

Conclusions:

Versatile bonding approaches enable the engineering of advanced organic soft materials.
Organic macrocycles and cages show promise in gas storage, thin films, liquid crystals, and catalysis.