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Synlett 2006(14): 2347-2348  
DOI: 10.1055/s-2006-949618
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© Georg Thieme Verlag Stuttgart · New York

Iodic Acid (HIO3)

Arash Ghorbani Choghamarani*a,b
a Chemistry Department, Faculty of Science, Bu-Ali Sina ­University, Hamadan, Iran
b Chemistry Building, The University of Western Ontario, ­London, ON N6A 5B7, Canada
e-Mail: a-ghorbani@basu.ac.ir; e-Mail: aghorban@uwo.ca;

Further Information

Publication History

Publication Date:
24 August 2006 (online)

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Biographical Sketches

Arash Ghorbani Choghamarani was born in Kermanshah, Iran in 1979. He finished his undergraduate studies in applied chemistry at Bu-Ali Sina University of Hamadan (2001) and received his M.Sc. in organic chemistry under the supervision of Prof. Mohammad Ali Zolfigola (2003) and subsequently began his Ph.D. studies in ­organic chemistry with the same supervisor. At present, he is working as a visiting graduate student under the supervision of Professor Robert H. E. Hudsonb at the University of Western Ontario, ­London, Ontario, Canada (since September 2005).His research interests focus on the application of new reagents in ­organic reactions, the synthesis of organic compounds and some bicyclic fluorescent nucleosides.

Introduction

Iodic acid (HIO3) has attracted much interest owing to its potential as oxidant, [1-8] reagent [9-12] and acidic source. [13] [14] The use of iodic acid has been known for a long time and has been widely employed in numerous and different ­organic reactions such as: oxidation of sulfides, [1] [3] iodination, [10] [12] deprotection, [13] nitrosation, [14] and dehydrogenation of aldehydes and ketones. [15] This reagent has several advantages: cost-effectiveness, non-toxicity, easy and clean workup of products.

Abstracts

(A) Patil et al. reported a useful method for the iodination of hydroxy aryl ketones; they showed a variety of ortho-hydroxy-substituted aromatic carbonyl compounds which were selectively iodinated in 81-87% yield by using iodine and iodic acid. [10]

(B) Zolfigol and co-workers have used HIO3 and NaNO2 in the ­presence of wet SiO2 as a nitrosating agent for the effective and ­selective nitrosation of secondary amines under mild and hetero­geneous conditions in good yields. [14]

(C) Shirini et al. reported a simple and efficient method for the oxidation of thiols to disulfides and sulfides to sulfoxides in 87-95% yield using aqueous HIO3 at room temperature. [3] Also Lakouraj and co-workers have explained the utility of HIO3 for oxidation of sulfides to sulfoxides in the presence of wet SiO2 under solvent-free conditions. [1]

(D) Ketoximes and aromatic aldoximes are converted to the corresponding carbonyl compounds with HIO3 under mild and heterogeneous conditions in CH2Cl2 at room temperature in 67-97% yields. [4] Also deoximation and dehydrazonation have been reported using HIO3 in the presence of wet SiO2 under solvent-free conditions. [16]

(E) A variety of aldehydes and ketones were readily and selectively transformed to 1,3-saturated aldehydes and ketones with HIO3 and I2O5 at 45-65 °C in good yields. [15]

(F) Hashemi and Akhbari showed the conversion of a variety of ­aromatic amines into their corresponding quinines under microwave irradiation. [8]

(G) A variety of thioacetals and thioketals were deprotected to the ­corresponding carbonyl compounds with HIO3 in the presence of wet SiO2 at room temperature under solvent-free conditions. [13]

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