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Synlett 2012(1): 155-156  
DOI: 10.1055/s-0031-1290114
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© Georg Thieme Verlag Stuttgart ˙ New York

Molecular Iodine

Xin Wen*
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
e-Mail: wenxin0219@163.com;
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Publication History

Publication Date:
13 December 2011 (online)

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Introduction

Molecular iodine is a bluish-black solid under standard conditions. It is highly soluble in nonpolar organic solvents and only slightly soluble in water owing to its lack of polarity. However, the solubility in water may be substantially increased in the presence of dissolved iodides due to the formation of triiodide ions. Since first discovered by Bernard Courtois in 1811 [¹b] the interest in utilization of molecular iodine in organic chemistry has increased dramatically due to its readily available, convenient, relatively cheap and environmental benign characteristics over the toxic heavy metals or complex regents. Many types of reactions can be promoted by iodine, [¹] [²] such as the oxidation of alcohols, C-C/C-N bond formation and formation of heterocycles, etc.

    References

  • 1a Togo H. Iida S. Synlett  2006,  2159 
  • 1b Jereb M. Vrazic D. Zupan M. Tetrahedron  2011,  67:  1355 
    Search in Google Scholar
  • 2a He ZH. Li HR. Li ZP. J. Org. Chem.  2010,  75:  4636 
    Search in Google Scholar
  • 2b Guillerm B. Monge S. Lapinte V. Robin JJ. Macromolecules  2010,  43:  5964 
    Search in Google Scholar
  • 2c Chen XP. Lu P. Wang YG. Chem. Eur. J.  2011,  17:  8105 
    Search in Google Scholar
  • 3 Nobuta T. Hirashima S. Tada N. Miura T. Itoh A. Org. Lett.  2011,  13:  2576 
    Search in Google Scholar
  • 4 Vasconcelos RS. Silva LFJr. Giannis A. J. Org. Chem.  2011,  76:  1499 
    Search in Google Scholar
  • 5 Li Y. Song D. Dong VM. J. Am. Chem. Soc.  2008,  130:  2962 
    Search in Google Scholar
  • 6 Okimoto Y. Kikuchi D. Sakaguchi S. Ishii Y. Tetrahedron Lett.  2000,  41:  10223 
    Search in Google Scholar
  • 7 Li YX. Ji KG. Wang HX. Ali S. Liang YM.
    J. Org. Chem.  2011,  76:  744 
    Search in Google Scholar
  • 8 Lamar AA. Nicholas KM. J. Org. Chem.  2010,  75:  7644 
    Search in Google Scholar
  • 9a Huard K. Lebel H. Chem. Eur. J.  2008,  14:  6222 
    Search in Google Scholar
  • 9b Pelletier G. Powell DA. Org. Lett.  2007,  8:  6031 
    Search in Google Scholar
  • 10 Mao JC. Hua QQ. Xie GL. Guo J. Yao ZG. Shi DQ. Ji SJ. Adv. Synth. Catal.  2009,  351:  635 
    Search in Google Scholar
  • 11 Lin C. Lai PT. Liao SKS. Hung WT. Yang WB. Fang JM. J. Org. Chem.  2008,  73:  3848 
    Search in Google Scholar
  • 12 Gogoi P. Hazarika P. Konwar D. J. Org. Chem.  2005,  70:  1934 
    Search in Google Scholar