J. Coustard
Apr 1, 2001
Citations
0
Influential Citations
15
Citations
Journal
European Journal of Organic Chemistry
Abstract
2-Nitro-1,1-bis(phenylalkylthio)ethene or 1-(methylthio)-2-nitro-1-(phenylalkylthio)ethene derivatives tethered to an aromatic ring undergo a fast intramolecular cyclization in trifluoromethanesulfonic acid, with the intermediate formation of dications, which can be detected by NMR spectroscopy. Quenching with methanol at low temperature affords cyclic orthothioesters of isothiochromanones, 4,5-dihydrobenzo[d]thiepin-1-one, 5,6-dihydro-4H-benzo[d]thiocin-1-one and 8,9,10,11-tetrahydro-7-thiabenzocyclononen-5-one oximes. The yields are usually fair to good, except for the nine-membered ring derivatives.