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

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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

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Publication details

The article was received on 01 Sep 2017, accepted on 04 Oct 2017 and first published on 08 Nov 2017


Article type: Communication
DOI: 10.1039/C7DT03243A
Citation: Dalton Trans., 2017, Advance Article
  • Open access: Creative Commons BY-NC license
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    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, Advance Article , DOI: 10.1039/C7DT03243A

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