Synthesis of new hybrid 1,4-thiazinyl-1,2,3-dithiazolyl radicals via Smiles rearrangementElectronic supplementary information (ESI) available: Full details of synthetic, spectroscopic, computational, and crystallographic work. CCDC 1519804-1519808, 1536800 and 1536801. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7dt03243a

• Main Authors: Vasko, Petra, Hurmalainen, Juha, Mansikkamäki, Akseli, Peuronen, Anssi, Mailman, Aaron, Tuononen, Heikki M
• Format: Article
• Language: English
• ISSN: 1477-9226; 1477-9234
• DOI: 10.1039/c7dt03243a

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. New hybrid 1,4-thiazine-1,2,3-dithiazolylium salts were prepared via Smiles rearrangement. The cations can be readily reduced to the corresponding stable neutral radicals with delocalised spin densities.