Issue 38, 2014
From the journal:

Chemical Communications

Non-innocent pyridyl nitrogens: unprecedented interconversion of N-bridgehead-thiadiazolium salts and thiatriazine in the generation of thiatriazinyl†

Alicea A. Leitch,a   Ilia Korobkov,a   Abdeljalil Assoudb  and  Jaclyn L. Brusso*a  

* Corresponding authors

a Department of Chemistry and Centre for Catalysis Research and Innovation, University of Ottawa, 10 Marie Curie, Ottawa, ON K1N 6N5, Canada
E-mail: jbrusso@uottawa.ca

b Department of Chemistry, University of Waterloo, Waterloo, ON N2L 3G1, Canada

Abstract

Condensation of N-2-pyridylimidoyl-2-pyridylamidine with S2Cl2 affords fused N-bridgehead-1,2,5-thiadiazolium salts, which can be converted to 3,5-bis(2-pyridyl)-4-hydro-1,2,4,6-thiatriazine (Py2TTAH). Oxidation of Py2TTAH with iodine yields the corresponding 1,2,4,6-thiatriazinyl radical, identified by EPR spectroscopy.

Graphical abstract: Non-innocent pyridyl nitrogens: unprecedented interconversion of N-bridgehead-thiadiazolium salts and thiatriazine in the generation of thiatriazinyl

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Article information

DOI
https://doi.org/10.1039/C4CC01433B
Article type
Communication
Submitted
24 Feb 2014
Accepted
27 Mar 2014
First published
04 Apr 2014
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2014,50, 4934-4936

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Non-innocent pyridyl nitrogens: unprecedented interconversion of N-bridgehead-thiadiazolium salts and thiatriazine in the generation of thiatriazinyl

A. A. Leitch, I. Korobkov, A. Assoud and J. L. Brusso, Chem. Commun., 2014, 50, 4934 DOI: 10.1039/C4CC01433B

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