A short, versatile route towards benzothiadiazinyl radicals

A family of substituted 1,2,4-benzothiadiazine 1-chlorides have been prepared by treatment of N-arylamidines in neat thionyl chloride at reflux. The S(iv) 1-chlorides are readily reduced under mild conditions to persistent 1,2,4-benzothiadiazinyl radicals which have been characterised by EPR spectro...

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Detalles Bibliográficos
Autores principales: Borys, Andryj M., Clark, Ewan R., Saines, Paul J., Alberola, Antonio, Rawson, Jeremy M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694340/
https://www.ncbi.nlm.nih.gov/pubmed/35059163
http://dx.doi.org/10.1039/d1sc04248c
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author Borys, Andryj M.
Clark, Ewan R.
Saines, Paul J.
Alberola, Antonio
Rawson, Jeremy M.
author_facet Borys, Andryj M.
Clark, Ewan R.
Saines, Paul J.
Alberola, Antonio
Rawson, Jeremy M.
author_sort Borys, Andryj M.
collection PubMed
description A family of substituted 1,2,4-benzothiadiazine 1-chlorides have been prepared by treatment of N-arylamidines in neat thionyl chloride at reflux. The S(iv) 1-chlorides are readily reduced under mild conditions to persistent 1,2,4-benzothiadiazinyl radicals which have been characterised by EPR spectroscopy and cyclic voltammetry. Crystallographic studies on isolated radicals indicate that the radicals dimerise via pancake bonding in the solid-state, resulting in spin-pairing and net diamagnetism.
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spelling pubmed-86943402022-01-19 A short, versatile route towards benzothiadiazinyl radicals Borys, Andryj M. Clark, Ewan R. Saines, Paul J. Alberola, Antonio Rawson, Jeremy M. Chem Sci Chemistry A family of substituted 1,2,4-benzothiadiazine 1-chlorides have been prepared by treatment of N-arylamidines in neat thionyl chloride at reflux. The S(iv) 1-chlorides are readily reduced under mild conditions to persistent 1,2,4-benzothiadiazinyl radicals which have been characterised by EPR spectroscopy and cyclic voltammetry. Crystallographic studies on isolated radicals indicate that the radicals dimerise via pancake bonding in the solid-state, resulting in spin-pairing and net diamagnetism. The Royal Society of Chemistry 2021-11-23 /pmc/articles/PMC8694340/ /pubmed/35059163 http://dx.doi.org/10.1039/d1sc04248c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Borys, Andryj M.
Clark, Ewan R.
Saines, Paul J.
Alberola, Antonio
Rawson, Jeremy M.
A short, versatile route towards benzothiadiazinyl radicals
title A short, versatile route towards benzothiadiazinyl radicals
title_full A short, versatile route towards benzothiadiazinyl radicals
title_fullStr A short, versatile route towards benzothiadiazinyl radicals
title_full_unstemmed A short, versatile route towards benzothiadiazinyl radicals
title_short A short, versatile route towards benzothiadiazinyl radicals
title_sort short, versatile route towards benzothiadiazinyl radicals
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694340/
https://www.ncbi.nlm.nih.gov/pubmed/35059163
http://dx.doi.org/10.1039/d1sc04248c
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