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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Volume 71, Issue 6


Selective di- and monochlorination of pyridazine-annelated bis(imidazolium) salts

Benjamin Raible
  • Institut für Anorganische Chemie, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, D-72070 Tübingen, Germany
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/ Doris Kunz
  • Corresponding author
  • Institut für Anorganische Chemie, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, D-72070 Tübingen, Germany, Tel.: +49 7071 29-72063, Fax: +49 7071 29-2436
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Published Online: 2016-04-20 | DOI: https://doi.org/10.1515/znb-2016-0010


A synthetic route for the selective di- and monochlorination of pyridazine annelated bis(imidazolium) salts at the formamidinium moieties with trichloroisocyanuric acid (TCCA) is presented. Due to the steric hindrance, the molecular structure of the dichlorobis(imidazolium) salt shows a pronounced torsion from planarity as well as a deviation of the C–Cl bond vectors from the ideal bisecting line of the respective NCN angles such as to avoid each other. The monochlorinated bis(imidazolium) salt is free of steric hindrance and therefore shows less deviation from the parent bis(imidazolium) salt. In the presence of acetate the chloroimidazolium salt acts as a chlorination agent for acetate leading to formation of acetyl chloride and the respective urea.

This article offers supplementary material which is provided at the end of the article.

Keywords: chlorination; chloroimidazolium salt; imidazolium salt; trichloroisocyanuric acid; urea


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About the article

Received: 2016-01-10

Accepted: 2016-01-22

Published Online: 2016-04-20

Published in Print: 2016-06-01

Citation Information: Zeitschrift für Naturforschung B, Volume 71, Issue 6, Pages 659–666, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2016-0010.

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