Oxidation/reduction interconversion of thiols and disulfides using hydrogen and oxygen catalyzed by a rhodium complex

Tetrahedron Letters

Volumn 46, Issue 36, 2005, Pages 6097-6099

  Arisawa, Mieko ^a   Sugata, Chiyoshi ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BUTANE; DISULFIDE; HYDROGEN; OXYGEN; RHODIUM COMPLEX; THIOL;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION REDUCTION REACTION;

EID: 23244453205     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.169     Document Type: Article

References (24)

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23. 4 (0.25 mol %, 5.76 mg) and di(2-pivaloyloxyethyl)disulfide (2 mmol, 644 mg) in toluene (4.0 mL) under a hydrogen atmosphere, and the solution was heated at reflux for 0.5 h. Then, the solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel giving 2-(pivaloyloxy)ethanethiol (593.8 mg, 92%).
24. 4 (17.3 mg, 0.1 mol %) and 1,4-diphenylphosphinobutane (dppb, 12.8 mg, 0.2 mol %) in methanol (30 mL) was freeze-evacuated, and was warmed to 40°C under an argon atmosphere. Then, 1-octanethiol (2.6 mL, 15 mmol) was added, and the argon balloon was exchanged to oxygen. The mixture was stirred for 1 h at the temperature, and passed through a short pad of silica gel to remove the rhodium complex. The solvent was removed under reduced pressure, and Kugel-Rhor distillation gave dioctyl disulfide (2.02 g, 93%).