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

<P>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.</P>

Abstracts

<TD VALIGN="TOP"> (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] </TD><TD VALIGN="TOP">

</TD><TD VALIGN="TOP"> (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] </TD><TD VALIGN="TOP">

</TD><TD VALIGN="TOP"> (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] </TD><TD VALIGN="TOP">

</TD><TD VALIGN="TOP"> (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] </TD><TD VALIGN="TOP">

</TD><TD VALIGN="TOP"> (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] </TD><TD VALIGN="TOP">

</TD><TD VALIGN="TOP"> (F) Hashemi and Akhbari showed the conversion of a variety of ­aromatic amines into their corresponding quinines under microwave irradiation. [8] </TD><TD VALIGN="TOP">

</TD><TD VALIGN="TOP"> (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] </TD><TD VALIGN="TOP">

</TD>

References

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<A NAME="RV17705ST-2">2</A> Fabian W. Z. Kristallogr.  1985,  170:  43 

<A NAME="RV17705ST-3">3</A> Shirini F. Zolfigol MA. Lakouraj MM. Azadbar MR. Russ. J. Org. Chem. (Engl. Transl.)  2001,  37:  1340 

<A NAME="RV17705ST-4">4</A> Chondrasekhar S. Gopalaiah K. Tetrahedron Lett.  2002,  43:  4023 

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<A NAME="RV17705ST-13">13</A> Lakouraj MM. Tajbakhsh M. Shrini F. Asady Tamami M MV. Phosphorus, Sulfur Silicon Relat. Elem.  2005,  180:  2423 

<A NAME="RV17705ST-14">14</A> Zolfigol MA. Ghorbani Choghamarani A. Shirini F. Keypour H. Salehzadeh S. Synth. Commun.  2001,  31:  359 

<A NAME="RV17705ST-15">15</A> Nicolaou KC. Montagnon T. Baran PS. Angew. Chem. Int. Ed.  2002,  41:  1386 

<A NAME="RV17705ST-16">16</A> Shirini F. Zolfigol MA. Azadbar MR. Synth. Commun.  2002,  32:  315