Deoximation of Oximes with 2-Iodylbenzoic Acid in Water in the Presence of β-Cyclodextrin
N. Srilakshmi Krishnaveni, K. Surendra, Y. V. D. Nageswar, K. Rama Rao*
*Organic Chemistry Division-I, Indian Institute of Chemical Technology,
Hyderabad-500 007, India, Email: drkrrao
yahoo.com
N. S. Krishnaveni, K. Surendra, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2003, 1968-1969.
DOI: 10.1055/s-2003-41448
Abstract
Oximes of various aldehydes and ketones can be converted to the corresponding carbonyl compounds at room temperature in excellent yields with 2-iodylbenzoic acid in water in the presence of β-cyclodextrin.
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Details
The document discusses a novel method for the deoximation of oximes to carbonyl compounds using 2-iodylbenzoic acid in water, catalyzed by β-cyclodextrin (β-CD). This method is environmentally friendly, operating at room temperature and yielding impressive results up to 96%. The process involves dissolving β-CD in water, adding the oxime and 2-iodylbenzoic acid, and stirring the mixture for 12 hours. The reaction is efficient for various oximes, especially those with aromatic moieties, and is compatible with different functional groups like halo, nitro, hydroxy, methoxy, and conjugated double bonds. β-CD acts as a catalyst by forming a complex with the oxime and 2-iodylbenzoic acid, facilitating the oxidation process. The reduced 2-iodylbenzoic acid can be recycled, and β-CD can be recovered and reused. This method offers several advantages over existing methodologies, such as the use of non-hazardous reagents, mild conditions, and high yields. The study highlights the potential of supramolecular catalysis in organic synthesis, providing a sustainable and efficient approach to deoximation.
N. S. Krishnaveni, K. Surendra, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2003, 2295-2297.
Key Words
IBX, β-cyclodextrin, water, oximes, aldehydes, ketones
ID: J66-Y2003-1970
