1-ARYLAMINO-1-METHYLTHIO-2-NITROETHENE IN SUPERACIDS - NMR-STUDY AND REACTIVITY OF THE FORMED HYDROXYNITRILIUM IONS

Authors
COUSTARD JM
Citation
Jm. Coustard, 1-ARYLAMINO-1-METHYLTHIO-2-NITROETHENE IN SUPERACIDS - NMR-STUDY AND REACTIVITY OF THE FORMED HYDROXYNITRILIUM IONS, Tetrahedron, 52(28), 1996, pp. 9509-9520
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
28
Year of publication
1996
Pages
9509 - 9520
Database
ISI
SICI code
0040-4020(1996)52:28<9509:1IS-NA>2.0.ZU;2-S
Abstract
At low temperature in triflic acid, 1-arylamino-1-methylthio-2-nitroet hylenes give firstly C,O-protonated species then 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 arylimino hydroxyimino derivatives. Intramolecular reaction occurs when temperat ure rises. Effect of aromatic ring substituant, acidity (HF-ShF(5) 5:1 ) and Z/E imine configuration are also discussed. Copyright (C) 1996 E lsevier Science Ltd