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DOI: 10.1055/s-0033-1340958
Mercury(II) Chloride
Publication History
Publication Date:
14 March 2014 (online)
Introduction
Organomercurials were among the first prepared organometallic compounds, being known since the second half of the 19th century.[1] [2] Despite their toxicity, mercury compounds are still used in the chemical and petrochemical industries. For instance, the industrial synthesis of vinyl chloride and acetaldehyde from acetylene is carried out using mercury catalysts.[3] Therefore, the study of environmental and health impacts of mercury and organomercurials, as well as the improvement of safety and handling techniques, are of great importance.
Mercury(II) chloride, HgCl2, is a commercially available mercury salt, and thus an important mercury(II) source. Besides novel mercuration reactions with organic substrates,[3] [4] [5] [6] [7] HgCl2 has been extensively used in a variety of cyclization reactions, forming both carbocycles and heterocycles.[8–10] Its use as inorganic thiophile has led to the formation of several new products from organosulfur reactants, especially thiocarbonyl compounds.[11] [12] [13] [14] [15] [16] Finally, the synthesis of mercury(II) alkynyls, mainly from HgCl2, and their use as building blocks for supramolecular structures has been reviewed.[17]
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References
- 1 Frankland E. Phil. Trans. R. Soc. 1852; 142: 417
- 2 Larock RC. Angew. Chem., Int. Ed. Engl. 1978; 17: 27
- 3 Cataldo F, Kanazirev V. Polyhedron 2013; 62: 42
- 4 Voinov MA, Grigor'ev IA. Tetrahedron Lett. 2002; 43: 2445
- 5 Voinov MA, Shevelev TG, Rybalova TV, Gatilov YV, Pervukhina NV, Burdukov AB, Grigor'ev IA. Organometallics 2007; 26: 1607
- 6 Liu L, Lam Y.-W, Wong W.-Y. J. Organomet. Chem. 2006; 691: 1092
- 7 Nagapradeep N, Verma S. Chem. Commun. 2011; 47: 1755
- 8 Atta AK, Kim S.-B, Heo J, Cho D.-G. Org. Lett. 2013; 15: 1072
- 9 Biswas G, Ghorai S, Bhattacharjya A. Org. Lett. 2006; 8: 313
- 10 Kaila JC, Baraiya AB, Pandya AN, Jalani HB, Sudarsanam V, Vasu KK. Tetrahedron Lett. 2010; 51: 1486
- 11 Cunha S, Rodrigues Jr. MT, da Silva CC, Napolitano HB, Vencato I, Lariucci C. Tetrahedron 2005; 61: 10536
- 12 Kaila JC, Baraiya AB, Vasu KK, Sudarsanam V. Tetrahedron Lett. 2008; 49: 7220
- 13 Kaila JC, Baraiya AB, Pandya AN, Jalani HB, Vasu KK, Sudarsanam V. Tetrahedron Lett. 2009; 50: 3955
- 14 O'Donovan DH, Rozas I. Tetrahedron Lett. 2011; 52: 4117
- 15 O'Donovan DH, Rozas I. Tetrahedron Lett. 2012; 53: 4532
- 16 Insuasty H, Insuasty B, Castro E, Quiroga J, Abonia R. Tetrahedron Lett. 2013; 54: 1722
- 17 Wong W-Y. Coord. Chem. Rev. 2007; 251: 2400
- 18 Varadaraju TG, Hwu JR. Org. Biomol. Chem. 2012; 10: 5456
- 19 Ramaligan C, Park Y.-T. J. Org. Chem. 2007; 72: 4536