The urea-hydrogen peroxide complex: Solid-state oxidative protocols for hydroxylated aldehydes and ketones (Dakin reaction), nitriles, sulfides, and nitrogen heterocycles

Organic Letters

Volumn 1, Issue 2, 1999, Pages 189-191

  Varma, Rajender S ^a   Naicker, Kannan P ^a  

^a SAM HOUSTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000370931     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990522n     Document Type: Article

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48. General Procedure for UHP Oxidation Reactions. The starting material (2 mmol) was added to the finely powdered urea-hydrogen peroxide adduct (376 mg, 4 mmol) in a glass test tube, and the reaction mixture was placed in an oil bath at 85°C for the specified time (Tables 1 and 2). After completion of the reaction, monitored by TLC (8:2 v/v, hexane: EtOAc), the reaction mixture was extracted into ethyl acetate and the combined extracts were washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford the crude product, which was purified by chromatography to deliver pure product, as confirmed by the spectral analysis.
49. Typical Procedure for Oxidation of Sulfides: Preparation of Methyl Phenyl Sulfoxide and Sulfone. In a typical experiment, methyl phenyl sulfide (248 mg, 2 mmol) was added to the finely powdered urea-hydrogen peroxide adduct (376 mg, 4 mmol) in a glass test tube, and the reaction mixture was placed in an oil bath at 85°C for 15 min for complete conversion of sulfide to sulfoxide with a trace amount (10%) of sulfone. For complete conversion of sulfide to sulfone, the reaction time was extended to 1 h (see Table 2). After completion of the reaction, monitored by TLC (8:2 v/v, hexane:EtOAc), the reaction mixture was extracted into ethyl acetate and the combined extracts were washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford the crude product, which was purified by chromatography on a silica gel column; fractions obtained with pure hexane as eluent afforded pure product (80% of sulfoxide), as confirmed by the spectral analysis.