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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.

C–C Bond Formation: Aldol Condensation Overview

C–C Bond Formation: Aldol Condensation Overview

Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.

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.

Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

Radical Formation: Homolysis

Radical Formation: Homolysis

A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.

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Related Experiment Video

Updated: Sep 29, 2025

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

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

Published on: June 20, 2014

C-H Bond Functionalization under Electrochemical Flow Conditions.

Tamlal Pokhrel¹, Bijaya B K¹, Ramesh Giri¹

¹Central Department of Chemistry, Tribhuvan University, Kirtipur, 44618, Kathmandu, Nepal.

Chemical Record (New York, N.Y.)

|March 22, 2022

Summary

Flow electrolysis enables sustainable and efficient electrochemical C-H functionalization for creating carbon-carbon and carbon-heteroatom bonds. This method offers improved selectivity and reduced byproducts in organic synthesis.

Keywords:

C−H bonds activation Flow electrochemistry Green and sustainable chemistry Microreactors Reaction engineering

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

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Area of Science:

Organic Synthesis
Electrochemistry
Sustainable Chemistry

Background:

Electrochemical C-H functionalization is gaining prominence in organic synthesis.
Flow electrolysis offers enhanced sustainability and efficiency over traditional methods.

Purpose of the Study:

To provide a comprehensive review of flow electrolysis for C-H functionalization.
To summarize recent advancements in constructing C-C and C-X bonds using this technique.

Main Methods:

Utilizing flow electro-reactors for C-H functionalization reactions.
Exploring applications in benzylic oxidation and synthesis of biologically active molecules.

Main Results:

Flow electrolysis facilitates shorter reaction times and safer working conditions.
The technique minimizes overoxidation and side product formation, improving selectivity.
Electrochemical processes can be managed without supporting electrolytes.

Conclusions:

Flow electrolysis is a powerful and sustainable tool for modern organic synthesis.
This method enables efficient construction of diverse molecular architectures.
It holds significant potential for accessing valuable chemical entities.