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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta catalyst, high molecular...
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Related Experiment Video

Updated: Jun 1, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Aza-Nazarov cyclization cascades.

Kiran Kumar Solingapuram Sai1, Matthew J O'Connor, Douglas A Klumpp

  • 1Department of Chemistry, Northern Illinois University, DeKalb, IL 60115, United States.

Tetrahedron Letters
|June 11, 2011
PubMed
Summary

Benzamides with acetal groups react in triflic acid to form ring-fused isoindolinones via a cyclization cascade. This reaction proceeds through an N-acyliminium ion intermediate, followed by an aza-Nazarov cyclization.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Benzamides are versatile organic compounds.
  • Acetal groups can participate in various chemical transformations.
  • Ring-fused heterocyclic compounds possess significant biological and material properties.

Purpose of the Study:

  • To investigate the reactivity of benzamides bearing tethered acetal groups.
  • To explore novel cyclization pathways for synthesizing isoindolinone derivatives.
  • To elucidate the mechanism of the observed cyclization cascade.

Main Methods:

  • Reaction of benzamides with tethered acetal groups in trifluoromethanesulfonic acid (CF(3)SO(3)H).
  • Analysis of reaction products using spectroscopic techniques.
  • Mechanistic studies involving intermediate identification.

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Related Experiment Videos

Last Updated: Jun 1, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Main Results:

  • Successful synthesis of ring-fused isoindolinones through a cyclization cascade.
  • Formation of an N-acyliminium ion intermediate.
  • Aza-Nazarov reaction as the key step in isoindolinone formation.
  • Observation of an unusual cyclization at the allylic position in a reaction variant.

Conclusions:

  • Benzamides with tethered acetal groups provide a facile route to isoindolinones.
  • The reaction proceeds via a proposed N-acyliminium ion and aza-Nazarov cyclization mechanism.
  • The study reveals a novel synthetic methodology for complex heterocyclic structures.