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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...

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.

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

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.

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Dearomatizing Photocyclization and Oxidative Aromatization: Constructing Polycyclic Arenes from Styrenes.

Dong Li¹, Tao Huang¹, Yuhang He¹

¹Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.

Chemistry, an Asian Journal

|January 20, 2025

Summary

Researchers developed a new organophotocatalysis method for synthesizing polycyclic aromatic compounds. This efficient cascade reaction uses simple styrene derivatives under mild conditions, offering a cost-effective route to valuable arenes.

Keywords:

[4+2] annulation aromatization photocyclization styrenes

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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

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Published on: November 29, 2018

Area of Science:

Organic Chemistry
Photocatalysis
Synthetic Methodology

Background:

Direct construction of polycyclic arenes is a significant challenge in organic synthesis.
Existing methods often require harsh conditions or complex starting materials.

Purpose of the Study:

To develop an efficient and mild method for synthesizing functionalized polycyclic aromatic compounds.
To utilize organophotocatalysis for a novel cascade reaction.

Main Methods:

A cascade reaction combining dearomatizing photocyclization and oxidative aromatization.
Organophotocatalysis under transition-metal-free conditions.
Utilizing readily available styrene derivatives as starting materials.

Main Results:

Achieved efficient synthesis of diverse functionalized polycyclic aromatic compounds.
Demonstrated good yields and regioselectivity in the reaction.
Operated under mild, metal-free conditions.

Conclusions:

The developed cascade reaction offers a straightforward and economical route to valuable polycyclic arenes.
This organophotocatalytic approach provides a sustainable alternative for arene synthesis.