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Abstract
Aryl methyl and aryl phenyl sulfides were prepared by the reaction of arenediazonium tetrafluoroborates with trimethyl(methylthio)- and trimethyl(phenylthio)silanes, respectively. In the latter case, addition of cupric sulfide was found to increase the yields. The main by-products were protodediazoniated products and diphenyl disulfide, which can be removed by treatment with aqueous sulfide and a base.
Highlights
The synthesis of aryl sulfides has attracted continued interest from the time of the discovery of the Ziegler reaction.[2]
Petrillo et al.[6] have dediazoniated arenediazonium tetrafluoroborates at room temperature in the presence of sodium arylthiolates in dimethylsulfoxide, a solvent supportive of electron transfer processes
Orthosubstituted arenediazonium salts reacting with trimethyl(methylthio)silane gave lower yields compared to para-substituted ones
Summary
The synthesis of aryl sulfides has attracted continued interest from the time of the discovery of the Ziegler reaction.[2]. A reported explosion.[5] Petrillo et al.[6] have dediazoniated arenediazonium tetrafluoroborates at room temperature in the presence of sodium arylthiolates in dimethylsulfoxide, a solvent supportive of electron transfer processes. A recent comprehensive report, in a modified Ziegler reaction, has employed stable and safe arenediazonium o-benzenesulfonimides for the preparation of a large number of alkyl aryl and diaryl sulfides using a number of aliphatic and aromatic thiolates under basic conditions.[7]
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