Tetrahedron p. 9509 - 9520 (1996)
Update date:2022-08-22
Topics:
Coustard, Jean-Marie
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.
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