Modified o-methyl-substituted IBX: room temperature oxidation of alcohols and sulfides in common organic solvents

Tetrahedron Letters

Volumn 49, Issue 1, 2008, Pages 80-84

  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

ALCOHOL; METHYL GROUP; ORGANIC SOLVENT; REAGENT; SULFIDE; SULFOXIDE;

ALCOHOL OXIDATION; ARTICLE; DESS MARTIN OXIDATION; ROOM TEMPERATURE; SOLUBILITY; STANDARD; SUBSTITUTION REACTION;

EID: 36549047871     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.013     Document Type: Article

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39. 5 322.9417; found 322.9416.
40. 16 Me-IBX (1.5 equiv) in 10.0 mL of acetone was stirred for 5-10 min, and to this mixture 1-2 mmol of the alcohol was introduced. The reaction mixture was stirred for appropriate duration (see Table 1). The progress of the reaction was monitored by TLC analysis. After completion of the reaction, the solid material from the reaction mixture was filtered. Concentration of the filtrate followed by silica gel column chromatography led to isolation of the pure oxidation product.
41. 4 and solvent removed in vacuo. Silica gel column chromatography of the crude mixture yielded the pure product, which was characterized by spectroscopic data.
42. Standard IBX is reported to explode, cf. Ref. 2. We have not observed such attributes for Me-IBX even at acetonitrile reflux.