ammonium pyrrolidinedithiocarbamate | 118535-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ammonium pyrrolidinedithiocarbamate
• 英文别名: N,N-tetramethylene-thiocarbamoyl-sulphenamide；S-(pyrrolidine-1-carbonothioyl)thiohydroxylamine；amino pyrrolidine-1-carbodithioate
• CAS: 118535-52-7
• 化学式: C₅H₁₀N₂S₂
• 分子量: 162.28
• InChiKey: ZXRVVSPLKXIMMD-UHFFFAOYSA-N

物化性质

• 沸点：
  273.2±23.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  86.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  硝基萘 、 ammonium pyrrolidinedithiocarbamate 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 生成 1-氨基-4-硝基萘
  参考文献：
  名称：

  Process for the preparation of aromatic amines

  摘要：

  电亲芳香化合物可以在碱的存在下与磺胺酰胺发生反应，形成相应的芳香胺。

  公开号：

  US05262539A1
• 作为产物：
  描述：

  吡咯烷二硫代甲酸铵盐 在 sodium hypochlorite 、 氨 作用下， 反应 0.5h， 生成 ammonium pyrrolidinedithiocarbamate
  参考文献：
  名称：

  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
• 作为试剂：
  描述：

  2-硝基苯甲醚 在 potassium tert-butylate 、 ammonium pyrrolidinedithiocarbamate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以39%的产率得到3-甲氧基-4-硝基苯胺
  参考文献：
  名称：

  Reactions of organic anions. 194. Amination of nitroarenes with sulfenamides via vicarious nucleophilic substitution of hydrogen

  摘要：

  Nitroarenes react with sulfenamides RSNH2 in the presence of strong bases to give p- and o-nitro-anilines.

  DOI：

  10.1021/jo00044a002

文献信息

• YONEMOTO, KATSUMI;SHIBUYA, ISAO;HONDA, KAZUMASA, BULL. CHEM. SOC. JAP., 61,(1988) N 6, 2232-2234
  作者：YONEMOTO, KATSUMI、SHIBUYA, ISAO、HONDA, KAZUMASA

  DOI：——

  日期：——
• Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen:  Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides
  作者：Mieczysław Ma̧kosza、Maciej Białecki

  DOI：10.1021/jo970582b

  日期：1998.7.1

  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.
• Process for the preparation of aromatic amines
  申请人：Bayer Aktiengesellschaft

  公开号：US05262539A1

  公开（公告）日：1993-11-16

  Electrophilic aromatic compounds can be reacted with sulphenamides in the presence of bases to form the corresponding aromatic amines.

  电亲芳香化合物可以在碱的存在下与磺胺酰胺发生反应，形成相应的芳香胺。