16619-55-9Relevant articles and documents
N,N-Dibromobenzenesulfonamide: A useful regenrable reagent for bromination of various carbanionic substrates
Tajbakhsh, Mahmood,Khazaei, Ardeshir,Mahalli, Majid Shabani,Vaghi, Ramin Ghorbani
, p. 1159 - 1163 (2004)
N,N-Dibromobenzenesulfonamide(dibromoamine-B), which is prepared easily in high yield, has been employed as effective brominating agent for carbanionic substrates under mild conditions. β-Diketones and β-ketoesters were brominated by this reagent without using any bases. The reagent can be recovered, rebrominated, and reused several times.
One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction
Chandra, Ajeet,Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
supporting information, p. 5827 - 5832 (2017/09/09)
Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.
Brominated methanes as photoresponsive molecular storage of elemental Br2
Kawakami, Kazumitsu,Tsuda, Akihiko
, p. 2240 - 2252 (2012/11/06)
The photochemical generation of elemental Br2 from brominated methanes is reported. Br2 was generated by the vaporization of carbon oxides and HBr through oxidative photodecomposition of brominated methanes under a 20 W low-pressure mercury lamp, wherein the amount and situations of Br2 generation were photochemically controllable. Liquid CH 2Br2 can be used not only as an organic solvent but also for the photoresponsive molecular storage of Br2, which is of great technical benefit in a variety of organic syntheses and in materials science. By taking advantage of the in situ generation of Br2 from the organic solvent itself, many organobromine compounds were synthesized in high practical yields with or without the addition of a catalyst. Herein, Br2 that was generated by the photodecomposition of CH2Br2 retained its reactivity in solution to undergo essentially the same reactions as those that were carried out with solutions of Br2 dissolved in CH 2Br2 that were prepared without photoirradiation. Furthermore, HBr, which was generated during the course of the photodecomposition of CH2Br2, was also available for the substitution of the OH group for the Br group and for the preparation of the HBr salts of amines. Furthermore, the photochemical generation of Br2 from CH2Br2 was available for the area-selective photochemical bleaching of natural colored plants, such as red rose petals, wherein Br2 that was generated photochemically from CH 2Br2 was painted onto the petal to cause radical oxidations of the chromophoric anthocyanin molecules. The generation of Br 2 from brominated methanes occurred upon photoirradiation under O2. The solutions that contained elemental Br2 were useful for the synthesis of organobromine compounds and the macroscopic photochemical bleaching of colored plants. Copyright
