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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.

Cycloaddition Reactions: Overview

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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.

Aromatic Hydrocarbon Cations: Structural Overview

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.
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Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

Cycloaddition Reactions: MO Requirements for Thermal Activation

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In cyclohexane, the substituents can occupy different positions generating distinct isomers.

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Related Experiment Video

Updated: Jul 5, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Published on: September 18, 2016

A cyclotrimerization route to cannabinoids.

Jesse A Teske¹, Alexander Deiters

¹North Carolina State University, Department of Chemistry, Raleigh, North Carolina 27695-8204, USA.

Organic Letters

|May 3, 2008

Summary

This summary is machine-generated.

Researchers synthesized three cannabinoid compounds, including cannabinol, using a novel microwave-assisted cyclotrimerization. This flexible method facilitates the creation of diverse cannabinoid analogs for further study.

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Synthetic Chemistry

Background:

Cannabinoids are a class of compounds with diverse biological activities.
Existing synthetic routes for cannabinoids can be complex and limited in scope.
Development of efficient synthetic strategies is crucial for exploring cannabinoid pharmacology.

Purpose of the Study:

To develop a novel and flexible synthetic route for key cannabinoid compounds.
To demonstrate the utility of microwave-mediated [2 + 2 + 2] cyclotrimerization in cannabinoid synthesis.
To enable the facile synthesis of cannabinoid analogues.

Main Methods:

Microwave-mediated [2 + 2 + 2] cyclotrimerization reaction was employed as the core synthetic step.
Synthesis of cannabinol, cannabinol methyl ether, and cannabinodiol was achieved.
The reaction conditions were optimized for efficiency and yield.

Main Results:

Successful synthesis of three distinct cannabinoid compounds.
The cyclotrimerization approach proved highly effective and versatile.
Demonstrated high synthetic flexibility for generating cannabinoid analogues.

Conclusions:

Microwave-mediated [2 + 2 + 2] cyclotrimerization offers a powerful and adaptable method for cannabinoid synthesis.
This approach significantly enhances the ability to create novel cannabinoid structures.
The methodology holds promise for future drug discovery efforts in the cannabinoid field.