Molecules p. 7 - 17 (2002)
Update date:2022-08-04
Topics: Isolation Reaction mixture Substituted Purification Preparation Precipitation Sulfides Methyl O-nitrophenyl
Dudova, Katerina
Castek, Frantisek
Machacek, Vladimir
Simunek, Petr
The nucleophilic substitution of substituted o-nitrochlorobenzenes with substituted methanethiolates, catalysed with triethylamine or pyridine, has been used to prepare a series of appropriately substituted methyl-o- nitrophenylsulfides. The prepared compounds were identified by their 1H- and 13C-NMR spectra. The base catalysed ring closure of methyl 2-(methoxycarbonylmethylsulfanyl)-3,5-dinitrobenzenecarboxylate only results in an attack of carbanion on the ester group, not on a nitro group as with the other compounds prepared. The cyclisation product is methyl 3-hydroxy-5,7-dinitro-benzo[b]thiophene-2-carboxylate (11).
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Doi:10.1021/ol026588r
(2002)Doi:10.1080/10426500212294
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(2002)Doi:10.1515/znb-1982-0823
(1982)Doi:10.1016/S0040-4039(03)00189-8
(2003)