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

: Vasko P, Hurmalainen J, Mansikkamaki A, Peuronen A, Mailman A, Tuononen HM

Publisher: ROYAL SOC CHEMISTRY

: 2017

: Dalton Transactions

: DALTON TRANSACTIONS

: DALTON T

: 46

: 16004

: 16008

: 5

: 1477-9226

DOI: https://doi.org/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.