About: Direct Amination of Nitro(pentafluorosulfanyl)benzenes through Vicarious Nucleophilic Substitution of Hydrogen     Goto   Sponge   NotDistinct   Permalink

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  • 1-Nitro-4-(pentafluorosulfanyl)benzene underwent direct amination with 1,1,1-trimethylhydrazinium iodide in the presence of tBuOK in DMSO to give 2-nitro-5-(pentafluorosulfanyl)aniline in good yield. 1-Nitro-3-(pentafluorosulfanyl)benzene, under similar conditions, gave 2-nitro-4(pentafluorosulfanyl)aniline, also in good yield. Reduction of either product with hydrogen in the presence of Raney nickel provided 4-(pentafluorosulfanyl)benzene-1,2-diamine, which served as a precursor for the efficient synthesis of SF5-containing benzimidazoles, quinoxalines, and benzotriazoles.
  • 1-Nitro-4-(pentafluorosulfanyl)benzene underwent direct amination with 1,1,1-trimethylhydrazinium iodide in the presence of tBuOK in DMSO to give 2-nitro-5-(pentafluorosulfanyl)aniline in good yield. 1-Nitro-3-(pentafluorosulfanyl)benzene, under similar conditions, gave 2-nitro-4(pentafluorosulfanyl)aniline, also in good yield. Reduction of either product with hydrogen in the presence of Raney nickel provided 4-(pentafluorosulfanyl)benzene-1,2-diamine, which served as a precursor for the efficient synthesis of SF5-containing benzimidazoles, quinoxalines, and benzotriazoles. (en)
Title
  • Direct Amination of Nitro(pentafluorosulfanyl)benzenes through Vicarious Nucleophilic Substitution of Hydrogen
  • Direct Amination of Nitro(pentafluorosulfanyl)benzenes through Vicarious Nucleophilic Substitution of Hydrogen (en)
skos:prefLabel
  • Direct Amination of Nitro(pentafluorosulfanyl)benzenes through Vicarious Nucleophilic Substitution of Hydrogen
  • Direct Amination of Nitro(pentafluorosulfanyl)benzenes through Vicarious Nucleophilic Substitution of Hydrogen (en)
skos:notation
  • RIV/61388963:_____/12:00376771!RIV13-AV0-61388963
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  • P(GAP207/12/0072), Z(AV0Z40550506)
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  • 11
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  • 131408
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  • RIV/61388963:_____/12:00376771
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  • sulfur; amination; nucleophilic substitution; nitrogen heterocycles (en)
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  • DE - Spolková republika Německo
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  • [5ACB8B3AFFFF]
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  • European Journal of Organic Chemistry
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  • Beier, Petr
  • Pohl, Radek
  • Pastýříková, Tereza
  • Iakobson, George
  • Vida, Norbert
http://linked.open...ain/vavai/riv/wos
  • 000302621400005
http://linked.open...n/vavai/riv/zamer
issn
  • 1434-193X
number of pages
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  • 10.1002/ejoc.201200127
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