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Related Experiment Video

Updated: Aug 12, 2025

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

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Published on: August 22, 2018

Piperazine Bridged Thianorrole Dimer.

Vratta Grover¹, Poornenth Pushpanandan¹, Mangalampalli Ravikanth¹

¹Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India.

Organic Letters

|February 1, 2023

Summary

Oxidative cyclization of thiabilanes unexpectedly formed piperazine-bridged thianorrole dimers. These unique dimers, linked by pyrrole C-C bonds, were found to be nonaromatic through spectral studies.

Area of Science:

Organic Chemistry
Heterocyclic Chemistry
Macromolecular Chemistry

Background:

Thiabilanes are sulfur-containing heterocyclic compounds.
Thianorroles are a class of sulfur-containing macrocycles.
Cyclization reactions are fundamental in organic synthesis.

Purpose of the Study:

To investigate the oxidative cyclization of open-chain thiabilanes.
To characterize the products formed from this reaction.
To determine the structural and electronic properties of the resulting compounds.

Main Methods:

Oxidative cyclization of open-chain thiabilanes.
Spectroscopic analysis (e.g., NMR, Mass Spectrometry) for structural elucidation.
Characterization of the macrocyclic products.

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

Main Results:

The study unexpectedly yielded piperazine-bridged thianorrole dimers instead of the anticipated monomeric thianorroles.
The dimeric structure features two thianorrole units linked by direct pyrrole C-C bonds, forming a bridging six-membered piperazine ring.
Spectral data confirmed the nonaromatic nature of the synthesized thianorrole dimers.

Conclusions:

Oxidative cyclization of thiabilanes provides a novel route to unique piperazine-bridged thianorrole dimers.
The formation of dimers highlights a new reactivity pathway for thiabilanes.
The nonaromatic character of the dimers has implications for their chemical behavior and potential applications.