132260-85-6

Upstream product

• 108-38-3 m-xylene 

Downstream Products

• 1379799-47-9 (2,4-dimethylphenyl) isopropyl sulfoxide 
• 20058-03-1 bis-(2,4-dimethylphenyl) sulfide 

Relevant academic research and scientific papers

Trifluoromethanesulfonic acid catalyzed preparation of symmetrical diaryl sulfoxides from arenes and thionyl chloride

The preparation of symmetrical diaryl sulfoxides from thionyl chloride and arenes catalyzed by trifluoromethanesulfonic acid is described. The reaction is characterized by its mildness, high yields, selectivity, and ease of workup.

Scandium triflate catalyzed one-pot synthesis of diaryl sulfoxides

Arenes react smoothly with thionyl chloride in the presence of a catalytic amount of scandium triflate at ambient temperature to afford the corresponding symmetrical diaryl sulfoxides in excellent yields with high regioselectivity.

Highly Rapid and Direct Synthesis of Diaryl Sulfoxides

Aromatic compounds react smoothly with thionyl chloride in the presence of 10 mol% of water at ambient temperature to afford the corresponding symmetrical diaryl sulfoxides in good to excellent yields with high regioselectivity.

Synthesis of o-Aryloxy Triarylsulfonium Salts via Aryne Insertion into Diaryl Sulfoxides

The aryne insertion into "S-O" bond has been validated recently. This technology is elusively applied to the synthesis of thioethers. In contrast to the reported cases, the reaction described furnished o-aryloxy triarylsulfonium salts, in lieu of thioethe

Desymmetrization of prochiral diaryl sulfoxides by an asymmetric sulfoxide-magnesium exchange

The first desymmetrizations of prochiral diaryl sulfoxides 1 by an asymmetric sulfoxide-magnesium exchange reaction are reported. The respective substrate (1), iPr2Mg, and the dilithium salt of (S)-BINOL (which was prepared in situ) provided (S)-configured aryl isopropyl sulfoxides 2 in up to 91 % yield and with up to 91 % ee. (S)-BINOL was re-isolable in 98 % yield. Copyright

Polystyrene and silica gel-supported, AlCl3-catalyzed preparation of diaryl sulfoxides from arenes and thionyl chloride

A simple, chemoselective, and efficient method has been developed for direct conversion of arenes to symmetrical diaryl sulfoxides using thionyl chloride in the presence of a catalytic amount of cross-linked polystyrene-supported aluminium chloride (Ps-AlCl3) and silica gel-supported aluminium chloride (SiO2-AlCl3). These solid acid catalysts are stable and can be easily recovered and reused without appreciable change in their efficiency. Copyright Taylor & Francis Group, LLC.

Reaction of Simple Arenes with FSO3H*SbF5/SO2: One-Pot Synthesis of Aromatic Sulfoxides. Mechanistic Aspects and Synthetic Utility

In a simple one-pot reaction, mono-, di-, tri-, and polyalkylbenzenes, isomeric alkylhalobenzenes, and fluoro-, (trifluoromethyl)-, and 1,3,5-trifluorobenzene were converted to their corresponding diaryl sulfoxides with FSO3H*SbF5 (1:1) (magic acid)/SO2.Dependency of the yields on the acidity (H0) and the arene structure was demonstrated.Reduction of the formed sulfoxide was also observed as a minor pathway to give diaryl sulfide.The reduction is superacid-catalyzed, and protonated sulfoxides are the key intermediates en route to sulfides.Protonation of several functionalized diaryl sulfoxides was also studied in magic acid/SO2 under stable ion conditions.Unlike the parent diphenyl sulfoxide, which is S-protonated, alkyl-, fluoro-, and trifluoromethyl-substituted diaryl sulfoxides O-protonate to give long-lived sulfoxonium ions.The proposed mechanism for the arene/superacid/SO2 system involves sulfination of the arenium ions, O-protonation of the resulting sulfinic acid, dehydration of the oxonium ion "ArSO+" and arylation.In the absence of SO2, the fluorosulfonation, ionization, arylation path becomes dominant.The scope of the reaction is sufficiently broad to be synthetically useful.The methodology is also applicable to unsymmetrical (mixed) diaryl sulfoxides.