Oxidations with IBX: Benzyl halides to carbonyl compounds, and the one-pot conversion of olefins to 1,2-diketones

Tetrahedron Letters

Volumn 47, Issue 11, 2006, Pages 1757-1761

  Moorthy, Jarugu Narasimha ^a   Singhal, Nidhi ^a   Senapati, Kalyan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 IODYLBENZOIC ACID; ALDEHYDE; ALKENE; BENZOIC ACID DERIVATIVE; BENZYL DERIVATIVE; CARBONYL DERIVATIVE; DIKETONE; DIMETHYL SULFOXIDE; HALIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; OXIDATION KINETICS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 32244447655     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.039     Document Type: Article

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31. 2 atmosphere. After completion of the reaction as determined by TLC analysis, the reaction mixture was quenched with water and the organic matter was extracted with ethyl acetate. Silica gel chromatography of the crude mixture yielded the products, which were characterized spectroscopically.
32. 2 atmosphere. The progress of the reaction was monitored by TLC analysis. As soon as the starting material disappeared, 3.0 equiv of IBX was introduced into the same pot and the reaction mixture was heated at 60-70°C. After completion of the reaction, it was quenched with water and extracted with ethyl acetate. The products were purified by silica gel chromatography and characterized spectroscopically.
33. The formation of alcohol was observed, as monitored from GC analysis, regardless of whether the reaction was run in freshly distilled DMSO or rigorously dried DMSO. By employing more equivalents of IBX, the yields of the oxidation products could be improved in addition to reducing the reaction time (cf. Table 1, entry 1).