Temperature-controlled selective reduction of arenesulfonyl chlorides promoted by samarium metal in DMF

Tetrahedron Letters

Volumn 44, Issue 22, 2003, Pages 4291-4294

  Liu, Yongjun ^a   Zhang, Yongmin ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Arenesulfonyl chloride; Diaryldisulfide; Diaryldisulfone; Diarylthiosulfonate; DMF; Samarium

Indexed keywords

CHLORIDE; METAL; N,N DIMETHYLFORMAMIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SAMARIUM; SULFIDE; SULFONE DERIVATIVE; SULFONIC ACID DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; REDUCTION; TEMPERATURE DEPENDENCE;

EID: 0038739142     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00814-1     Document Type: Article

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52. 4. The solvents were removed under reduced pressure to give the crude product, which was purified by column chromatography to afford diphenyldisulfone in 58% yield. Preparation of diphenylthiosulfonate: To a mixture of Sm powder (3 mmol) in freshly distilled N,N-dimethylformamide (DMF, 10 mL), benzenesulfonyl chloride (2 mmol, freshly distilled) was added at 5°C with magnetic stirring under a nitrogen atmosphere. The resulting solution turned yellow-green within 15 min and an exothermic reaction was observed. After the completion of the reaction (about 1 h at 5°C), a routine workup as mentioned above afforded diphenylthiosulfonate in 87% yield. Preparation of diphenyldisulfide: To a mixture of Sm powder (4 mmol) in freshly distilled N,N-dimethylformamide (DMF, 10 mL) benzenesulfonyl chloride (2 mmol, freshly distilled) was added at 50°C with magnetic stirring under a nitrogen atmosphere. The resulting solution turned yellow-green within 1 min and an exothermic reaction was observed. After the completion of the reaction (about 10 min), a routine workup as mentioned above afforded diphenyldisulfide in 93% yield.
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