ORGLIST:reaction of thiophenolate and clorobenzenesulfonate

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From: antonio regla (areglac$##$yahoo.com)
Date: Mon Feb 17 2003 - 19:29:18 EST

Dear list members:

I have been trying to react a thiophenolate with 4-chlorobenzenesulfonate in a variety of conditions, and haven't been succesful. Has anyone run this type of reactions? that is, nucleophilic aromatic substitutions on chlorobenzensulfonates? Most of the organic texts use nitrochlorobenzenes as example, and the sulfonic acid group is listed as an activator towards this type of reaction, however I haven't come across any experimental details as to the type of solvent and reaction temperatures. I have the feeling that temperatures above 100oC are required and I have tried refluxing DMF without success. If anyone has some idea, or previous experience with this type of reaction, please let me know. I do appreciate your valuable help.

Sincerely,

J. Antonio Regla

Facultad de Farmacia U.A.E.M.

Cuernavaca, Mexico

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