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Related Concept Videos

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Halogenation of Alkenes

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Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Elimination Reactions02:25

Elimination Reactions

A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called β elimination or...
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Electrophilic Addition to Alkynes: Hydrohalogenation

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Related Experiment Video

Updated: May 14, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Iodide-catalyzed halocyclization/cycloaddition/elimination cascade reaction.

Ulrich Kloeckner1, Peter Finkbeiner, Boris J Nachtsheim

  • 1Institute of Organic Chemistry, Eberhard Karls University Tuebingen, Auf der Morgenstelle 18, D-72076 Tuebingen, Germany.

The Journal of Organic Chemistry
|February 5, 2013
PubMed
Summary

A novel catalytic iodocyclization reaction efficiently synthesizes highly substituted 1-naphthalenones using tetrabutylammonium iodide (TBAI) and Oxone. This method offers a green and effective approach for synthesizing valuable organic compounds.

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Last Updated: May 14, 2026

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12:27

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

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

Published on: February 7, 2019

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Iodocyclization reactions are crucial for synthesizing heterocyclic compounds.
  • Developing catalytic methods for iodocyclization is essential for efficiency and sustainability.
  • Electrophilic iodine sources often require stoichiometric amounts, limiting their catalytic application.

Purpose of the Study:

  • To report a truly catalytic iodocyclization reaction for o-alkynylphenyl carboxaldehydes.
  • To develop a high-yielding synthesis of highly substituted 1-naphthalenones.
  • To explore the use of tetrabutylammonium iodide (TBAI) and Oxone in a catalytic system.

Main Methods:

  • Utilizing o-alkynylphenyl carboxaldehydes as substrates.
  • Employing tetrabutylammonium iodide (TBAI) as the iodine source catalyst.
  • Using Oxone as a co-oxidant in fluorinated protic solvents.

Main Results:

  • Achieved a truly catalytic iodocyclization reaction with respect to the iodine source.
  • Synthesized highly substituted 1-naphthalenones in high yields, up to 91%.
  • Demonstrated the effectiveness of TBAI and Oxone in fluorinated protic solvents.

Conclusions:

  • The developed method provides an efficient and catalytic route to 1-naphthalenones.
  • The use of TBAI and Oxone offers a practical and sustainable approach.
  • This reaction expands the toolkit for synthesizing complex organic molecules.