📜硝基氯苯置于potassium Tert-Butylate,Ammonium Pyrrolidinedithiocarbamate体系中,用 N,N-二甲基甲酰胺 作为反应溶剂,化学反应 0.33H,以72%的收率获得产物3-氯-4-硝基苯胺
参考文献:Nitroarylamines Via The Vicarious Nucleophilic Substitution Of Hydrogen: Amination,Alkylamination,And Arylamination Of Nitroarenes With Sulfenamides
标题:Nitroarylamines Via The Vicarious Nucleophilic Substitution Of Hydrogen: Amination,Alkylamination,And Arylamination Of Nitroarenes With Sulfenamides
摘要:A New Reaction Of Sulfenamides With Electrophilic Arenes Under Basic Conditions Is Described. The Sigma Adducts Formed From Nitroarenes And The Anions Of Sulfenamides Undergo Elimination Of Thiol To Produce The Corresponding O-And/or P-Nitroanilines. This Reaction Is Analogous To The Known Alkylation And Hydroxylation Of Nitroarenes Via The Vicarious Nucleophilic Substitution Of Hydrogen (Vns). The Reaction Gives Access To A Wide Range Of Substituted Nitroanilines,Nitronaphthylamines,And Aminoheterocycles. By Means Of The Reaction With N-Alkryl-And N-Arylsulfenamides,It Is Possible To Obtain N-Alkylnitroanilines And Nitrodiarylamines. By Varying The Structure Of Sulfenamide And The Reaction Conditions,Particularly The Nature And Concentration Of The Base,It Is Possible To Control The Orientation Of Amination.
DOI:10.1021/jo970582B