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Molecules 2002, 7(1), 7-17; doi:10.3390/70100007
Article

Preparation of Substituted Methyl o-Nitrophenyl Sulfides

, , *  and
Received: 27 September 2001 / Revised: 9 November 2001 / Accepted: 13 November 2001 / Published: 31 January 2002
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Abstract: 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-dinitrobenzo[b]thiophene-2-carboxylate (11).
Keywords: Nucleophilic aromatic substitution; sulfur nucleophiles; ring closure Nucleophilic aromatic substitution; sulfur nucleophiles; ring closure
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Dudova, K.; Castek, F.; Machacek, V.; Simunek, P. Preparation of Substituted Methyl o-Nitrophenyl Sulfides. Molecules 2002, 7, 7-17.

AMA Style

Dudova K, Castek F, Machacek V, Simunek P. Preparation of Substituted Methyl o-Nitrophenyl Sulfides. Molecules. 2002; 7(1):7-17.

Chicago/Turabian Style

Dudova, Katerina; Castek, Frantisek; Machacek, Vladimir; Simunek, Petr. 2002. "Preparation of Substituted Methyl o-Nitrophenyl Sulfides." Molecules 7, no. 1: 7-17.


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