- Ring halogenations of polyalkylbenzenes with N-halosuccinimide and acidic catalysts
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1-Bromo-2,5-pyrrolidinedione (NBS) and 1-chloro-2,5-pyrrolidinedione (NCS) with catalytic quantities of p-toluenesulfonic acid have been used for ring halogenations of polyalkylbenzenes. [Hydroxy(tosyloxy)iodo]benzene was effective as a catalyst with NBS but not NCS. Competition experiments with 1-iodo-2,5-pyrrolidinedione (NIS) were run to indicate selectivities in substrates, halogen sources and catalysts. With this information a mixed halogenated compound, 2-bromo-4-iodo-1,3,5-trimethylbenzene was prepared in high yield.
- Bovonsombat,McNelis
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- Ring Halogenations of Polyalkylbenzenes by Ionic Halides and Koser's Reagent
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Ring chlorinations of polyalkylbenzenes such as mesitylene have been carried out at room temperature with LiCl or NaCl and stoichiometric amounts of Koser's reagent.Solvent range from water to methylene chloride.The procedures were extended to bromination and iodination.
- Bovonsombat, Pakorn,Djuardi, Elsa,Nelis, Edward Mc
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- Halogenation Using Quaternary Ammonium Polyhalides. XIV. Aromatic Bromination and Iodination of Arenes by Use of Benzyltrimethylammonium Polyhalides-Zinc Chloride System
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The reaction of arenes with benzyltrimethylammonium tribromide or benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 deg C gave brome- or iodo-substituted arenes in good yield, respectively.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Tanaka, Toshio,Fujisaki, Shizuo,Okamoto, Tsuyoshi
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p. 439 - 443
(2007/10/02)
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