3085-42-5Relevant articles and documents
Iron(III) chloride (FeCl3)-catalyzed electrophilic aromatic substitution of chlorobenzene with thionyl chloride (SOCl2) and the accompanying auto-redox in sulfur to give diaryl sulfides (Ar2S): Comparison to catalysis by aluminum chloride (AlCl3)
Sun, Xiaoping,Haas, David,Lockhart, Chyress
, p. 376 - 380 (2017)
The Lewis acids MCl3(M = Fe and Al)-catalyzed electrophilic aromatic (ArH) substitution reactions with thionyl chloride (SOCl2) have been shown to give diaryl sulfoxide (Ar2SO) and the reduced diaryl sulfide (Ar2S). Under various selected conditions, the FeCl3-catalyzed reactions of chlorobenzene gave substantially much higher percent yields of Ar2S (Ar = p-ClC6H4) than the reactions catalyzed by AlCl3, showing that FeCl3facilitates the reduction in the sulfur center of SOCl2. A dπ?>pπ*back bond between Fe(III) and the O?S group is thought to be responsible for enhancement of the reduction.
PROCESS FOR PRODUCING 4,4'-DICHLORODIPHENYL SULFONE
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Page/Page column 31-32, (2021/03/05)
The invention relates to a process for producing 4,4'-dichlorodiphenyl sulfone, comprising: (I) reacting thionyl chloride, chlorobenzene and aluminum chloride forming an intermediate reaction product and hydrogen chloride; (II) mixing aqueous hydrochloric acid and the intermediate reaction product to obtain an organic phase comprising 4,4'-dichlorodiphenyl sulfoxide and an aqueous phase; (III) cooling the organic phase to a temperature below the saturation point of 4,4'- dichlorodiphenyl sulfoxide to obtain a suspension; (IV) solid-liquid-separation of the suspension to obtain crystallized 4,4'-dichlorodiphenyl sulfoxide, and mother liquor; (V) washing the crystallized 4,4'-dichlorodiphenyl sulfoxide with a carboxylic acid to obtain carboxylic acid-wet 4,4'-dichlorodiphenyl sulfoxide; (VI) reacting the washed 4,4'-dichlorodiphenyl sulfoxide and an oxidizing agent in a carboxylic acid as solvent to obtain a reaction mixture comprising 4,4'-dichlorodiphenyl sulfone and carboxylic acid; (VII) separating the reaction mixture comprising 4,4'-dichlorodiphenyl sulfone and carboxylic acid into a residual moisture comprising 4,4'-dichlorodiphenyl sulfone as crude product and a liquid phase comprising carboxylic acid.
Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide
Cao, Zhong-Yan,Li, Xiaolong,Lu, Hao,Wang, Panpan,Wang, Shengqiang,Xu, Xiaobo,Yan, Leyu,Yang, A-Xiu
supporting information, p. 8691 - 8695 (2021/10/22)
A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.