172531-53-2Relevant academic research and scientific papers
1-Arylamino-1-methylthio-2-nitroethene in superacids: NMR study and reactivity of the formed hydroxynitrilium ions
Coustard, Jean-Marie
, p. 9509 - 9520 (1996)
At low temperature in triflic acid, 1-arylamino-1-methylthio-2- nitroathylenes give firstly C,O-protonated species than a conjugated dication with aryliminium and hydroxynitrilium sites. The last one was trapped in situ with aromatic or quenched with MeOH or MeSH to form aryliminohydroxyimino derivatives. Intramolecular reaction occurs when temperature rises. Effect of aromatic ring substituent, acidity (HF-SbF5 5:1) and Z/E imino configuration are also discussed.
1,1-bis(Methylthio)-2-Nitroethene in Superacids: NMR Study and Reactivity of the Formed Hydroxynitrillium Ion.
Coustard, Jean-Marie
, p. 10929 - 10940 (2007/10/02)
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.
