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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 22
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Original Articles

Convenient, Mild Catalytic Deprotection of Oximes to Carbonyl Compounds with Hydrogen Peroxide and Iodine Catalyst in Aqueous Acetonitrile

, &
Pages 4053-4061 | Received 19 Nov 2008, Published online: 16 Oct 2009
 

Abstract

A clean, mild, and efficient catalytic deoximation procedure compatible with several common functional groups has been developed using 30% hydrogen peroxide activated by iodine catalyst in aqueous acetonitrile under essentially neutral conditions. The mechanistic features of an iodonium ion–driven nucleophilic cleavage of oximic C[dbnd]N have been revealed.

ACKNOWLEDGMENTS

S. K. B. thanks the University of Kalyani for financial assistance by way of a research fellowship. Facilities provided by the Department of Science and Technology–Funding for Infrastructure in Science and Technology and the University Grants Commission, Government of India, are also acknowledged.

Notes

a Reaction conditions: 30% H2O2 (0.22 mL) and I2 (10 mol%) per mmol of substrate in acetonitrile–water (9:1), rt.

b Isolated yield upon column chromatography; the carbonyl compounds were characterized by their spectral data (FTIR, 1H NMR), mp, and comparison with authentic sample.[ Citation 12 ]

c Reaction conditions: 30% H2O2 (0.22 ml) and I2 (10 mol%) per mmol of substrate, MeOH, rt.

d Reaction conditions: 30% H2O2 (0.22 mL) and I2 (50 mol%), and MeOH (2 mL) per mmol of substrate; 4-hydroxy-3,5-diiodoacetophenone oxime (8a) was formed in a yield of 10%.

e The low yield of acetophenone is due to concomitant formation of 4-amino-3-iodoacetophenone oxime (9a) in 8% yield.

f Acetic acid was used as the solvent because of the low solubility of the substrate in aqueous acetonitrile.

g NR indicates no reaction.

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