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DOI: 10.1055/s-0030-1258020
Bromotrichloromethane
Publication History
Publication Date:
16 August 2010 (online)
Introduction
Readily synthesized by Meunier et al. [¹] in 1938, bromotrichloromethane (BrCCl3) is a reagent of choice in organic synthesis. In recent years, many applications of this reagent have been reported. It can be used to synthesize esters, oxidize heterocycles, allow alkoxyl ring-closure reactions, perform α-bromination of sulfones, achieve radical addition on alkenes and radical cyclization of 1,6-dienes or synthesize dichloroalkenes. Some of these reactions were used at a final stage of complex total syntheses. Moreover, bromotrichloromethane is cheap, commercially available and stable at room temperature without any observed decomposition.
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Simons JH.Sloat TK.Meunier AC. J. Am. Chem. Soc. 1938, 61: 435 - 2
Otera J. Angew. Chem. Int. Ed. 2001, 40: 2044 - 3
Lee AS.-Y.Yang H.-C.Su F.-Y. Tetrahedron Lett. 2001, 42: 301 - 4
Hwu JR.Hsu C.-Y.Jain ML. Tetrahedron Lett. 2004, 45: 5151 - 5a
You S.-L.Kelly JW. Tetrahedron Lett. 2005, 46: 2567 - 5b
Bagley MC.Chapanei K.Dale JW.Xiong X.Bower J. J. Org. Chem. 2005, 70: 1389 - 6a
Mislin GL.Burger A.Abdallah MA. Tetrahedron 2004, 60: 12139 - 6b
Bowers AA.West N.Newkirk TL.Troutman-Youngman AE.Schreiber SL.Wiest O.Bradner JE.Williams RM. Org. Lett. 2009, 11: 1301 - 7
Chorell E.Das P.Almqvist F. J. Org. Chem. 2007, 72: 4917 - 8a
Hartung J.Knever R. Eur. J. Org. Chem. 2000, 1677 - 8b
Hartung J.Knever R. Tetrahedron: Asymmetry 2003, 14: 3019 - 9
Meyers CY.Chan-Yu-King R.Hua DH.Kolb VM.Matthews WS.Parady TE.Horii T.Sandrock PB.Hou Y.Xie S. J. Org. Chem. 2003, 68: 500 - 10
Heintz M.Le NyC.Nedelec JY. Tetrahedron Lett. 1984, 25: 5767 - 11
Mirzabekova NS.Kuz’mina NE.Lukashov OI.Sokolova NA.Golosov SN.Kazakov PV.Perlova TG.Potapova VV.Kheinman VA.Ivanova GB. Russ. J. Org. Chem. 2008, 44: 1139 - 12a
Gilbert BC.Parsons AF. J. Chem. Soc., Perkin Trans. 2 2002, 367 - 12b
Huther N.McGrail PT.Parsons AF. Eur. J. Org. Chem. 2004, 1740 - 13
Nenajdenko VG.Shastin AV.Muzalevskii VM.Balenkova ES. Russ. Chem. Bull., Int. Ed. 2004, 2647