140200-30-2Relevant academic research and scientific papers
Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions
Jereb, Marjan,Hribernik, Luka
supporting information, p. 2286 - 2295 (2017/07/24)
An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and "filtered" over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A "one-pot" protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.
Reaction of polyfluoroarenesulfonyl bromides with allyl bromide. Synthesis of allyl polyfluoroaryl sulfones
Bredikhin,Maksimov,Platonov
experimental part, p. 374 - 378 (2011/06/26)
Reactions of polyfluoroarenesulfonyl bromides 4-XC6F 4SO2Br (X = F, H, Cl, Br, CF3) with allyl bromide gave 84-94% of the corresponding allyl polyfluoroaryl sulfones.
A novel and efficient method for the synthesis of polyfluoroarenesulfonyl bromides from polyfluoroarenethiols
Platonov, Vyacheslav E.,Bredikhin, Roman A.,Maksimov, Alexander M.,Kireenkov, Victor V.
scheme or table, p. 13 - 16 (2010/06/11)
The first general methodology has been developed for the synthesis of polyfluoroarenesulfonyl bromides from polyfluoroarenethiols. At heating of polyfluoroarenethiols with a mixture of Br2 and fuming HNO3 or Br2, HNO3 and H2SO4 polyfluoroarenesulfonyl bromides were obtained in good yields.
