Issue 46, 2017

Synthesis of new hybrid 1,4-thiazinyl-1,2,3-dithiazolyl radicals via Smiles rearrangement

Abstract

The condensation reaction of 2-aminobenzenethiols and 3-aminopyrazinethiols with 2-amino-6-fluoro-N-methylpyridinium triflate afforded thioether derivatives that were found to undergo Smiles rearrangement and cyclocondensation with sulphur monochloride to yield new hybrid 1,4-thiazine-1,2,3-dithiazolylium cations. The synthesized cations were readily reduced to the corresponding stable neutral radicals with spin densities delocalized over both 1,4-thiazinyl and 1,2,3-dithiazolyl moieties.

Graphical abstract: Synthesis of new hybrid 1,4-thiazinyl-1,2,3-dithiazolyl radicals via Smiles rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
01 Sep 2017
Accepted
04 Oct 2017
First published
08 Nov 2017
This article is Open Access
Creative Commons BY-NC license

Dalton Trans., 2017,46, 16004-16008

Synthesis of new hybrid 1,4-thiazinyl-1,2,3-dithiazolyl radicals via Smiles rearrangement

P. Vasko, J. Hurmalainen, A. Mansikkamäki, A. Peuronen, A. Mailman and H. M. Tuononen, Dalton Trans., 2017, 46, 16004 DOI: 10.1039/C7DT03243A

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