Iodic Acid (HIO₃)

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 Zolfigol^a (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. Hudson^b 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]

References

• 1 Lakouraj MM. Tajbakhsh M. Shirini F. Asady Tamami MV. Synth. Commun.  2005,  35:  775 
• 2 Fabian W. Z. Kristallogr.  1985,  170:  43 
• 3 Shirini F. Zolfigol MA. Lakouraj MM. Azadbar MR. Russ. J. Org. Chem. (Engl. Transl.)  2001,  37:  1340 
• 4 Chondrasekhar S. Gopalaiah K. Tetrahedron Lett.  2002,  43:  4023 
• 5 Hashemi MM. Akhbari M. Russ. J. Org. Chem. (Engl. Transl.)  2005,  631:  1574 
• 6 Hashemi MM. Rahimi A. Karimi-Jaberi Z. Acta Chim. Slov.  2005,  52:  86 
• 7 Hashemi MM. Rahimi A. Ahmadibeni Y. Acta Chim. Slov.  2004,  51:  333 
• 8 Hashemi MM. Akhbari M. Monatsh. Chem.  2003,  1561 
• 9 Lio W. Zhou J. Wong J. Anal. Biochem.  1982,  120:  204 
• 10 Patil BR. Bhusare SR. Pawar RP. Vibhute YB. Tetrahedron Lett.  2005,  46:  7179 
• 11 Dawane BS. Vibhute YB. J. Indian Chem. Soc.  2000,  77:  299 
• 12 Krassowska-Swiebocka B. Prokopienko G. Skulski L. Molecules  2005,  10:  394 
• 13 Lakouraj MM. Tajbakhsh M. Shrini F. Asady Tamami M MV. Phosphorus, Sulfur Silicon Relat. Elem.  2005,  180:  2423 
• 14 Zolfigol MA. Ghorbani Choghamarani A. Shirini F. Keypour H. Salehzadeh S. Synth. Commun.  2001,  31:  359 
• 15 Nicolaou KC. Montagnon T. Baran PS. Angew. Chem. Int. Ed.  2002,  41:  1386 
• 16 Shirini F. Zolfigol MA. Azadbar MR. Synth. Commun.  2002,  32:  315