1,1-bis(Methylthio)-2-Nitroethene in Superacids: NMR Study and Reactivity of the Formed Hydroxynitrillium Ion.

Article abstract of DOI:10.1016/0040-4020(95)00669-Y

At low temperature in superacids TFSA or HF-SbF5, 1,1-bis(methylthio)-2-nitroethene yields a stable dication with hydroxynitrilium and bis(methylthio)carbocationic sites.The first site can be trapped in situ with suitable nucleophiles (aromatics, fluoride).Both sites can be trapped when the acidity is destroyed with MeOH or MeSH, to form in fair to good yield the corresponding α-hydroxyiminoorthothioester or the furoxane orthothioester.