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Related Concept Videos

Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak carbon–halogen...
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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.
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Cycloaddition Reactions: Overview

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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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Related Experiment Video

Updated: Jun 5, 2026

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

Intramolecular oxidative C-H coupling for medium-ring synthesis.

Didier G Pintori1, Michael F Greaney

  • 1EastChem, School of Chemistry, University of Edinburgh, King's Buildings, West Mains Rd, Edinburgh EH9 3JJ, UK.

Journal of the American Chemical Society
|January 4, 2011
PubMed
Summary

This study introduces a novel oxidative C-H coupling method for creating medium-sized rings. This breakthrough offers a new pathway for synthesizing complex medium-ring structures efficiently.

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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 Chemistry
  • Synthetic Chemistry

Background:

  • Medium-sized rings (7-11 members) are prevalent in natural products but challenging to synthesize.
  • Traditional methods for medium-ring synthesis often suffer from low yields and require harsh conditions.

Purpose of the Study:

  • To develop a novel and efficient method for the synthesis of medium-sized rings.
  • To establish an oxidative C-H coupling strategy for accessing these important structural motifs.

Main Methods:

  • Utilized a catalytic oxidative C-H coupling reaction.
  • Employed specific reaction conditions to promote intramolecular cyclization.

Main Results:

  • Successfully synthesized various medium-ring compounds.
  • Demonstrated the efficiency and broad applicability of the oxidative C-H coupling approach.

Conclusions:

  • The developed oxidative C-H coupling provides a powerful new tool for medium-ring synthesis.
  • This method offers a more sustainable and efficient alternative to existing strategies.