S,S-diphenyl-N-(2,4-dinitrophenylsulfenyl)-N'-tosylsulfodiimide | 924628-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S,S-diphenyl-N-(2,4-dinitrophenylsulfenyl)-N'-tosylsulfodiimide
• 英文别名: N-[(2,4-dinitrophenyl)sulfanylimino-diphenyl-lambda6-sulfanylidene]-4-methylbenzenesulfonamide；N-[(2,4-dinitrophenyl)sulfanylimino-diphenyl-λ6-sulfanylidene]-4-methylbenzenesulfonamide
• CAS: 924628-82-0
• 化学式: C₂₅H₂₀N₄O₆S₃
• 分子量: 568.655
• InChiKey: WAXQPSWXTMCSQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  193
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  S,S-diphenyl-N-(2,4-dinitrophenylsulfenyl)-N'-tosylsulfodiimide 在 二甲基亚砜 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以96%的产率得到
  参考文献：
  名称：

  Moderate generation of sulfenylnitrenes from novel N-sulfenylsulfodiimides

  摘要：

  N-Sulfenylated sulfodiimides were first prepared by the reaction of S,S-diphenyl-N-tosylsulfodiimide with arenesulfenyl chlorides under the basic conditions. Thermolysis of S,S-diphenyl-N-(2-nitrophenylsulfenyl)- and S,S-diphenyl-N-(2,4-dinitrophenylsulfenyl)sulfodiimides in the presence of olefins proceeded at 50-80 degrees C to give the corresponding deiminated S,S-diphenyl-N-tosylsulfimide and N-sulfenylaziridines in very good yields. 2,4-Dinitrophenyl-sulfenylnitrene was trapped by trans- and cis-l-phenylpropenes stereospecifically. The thermolysis temperature of the N-sulfenylsulfodiimides was found to be lower than N-sulfenylsulfoximide and higher than N-sulfenyliminosulfonium salt and very effective to trap the sulfenylnitrene to give the N-sulfenylaziridines in very good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.078
• 作为产物：
  描述：

  N-(iminodiphenyl-λ⁶-sulfanylidene)-4-methylbenzenesulfonamide 、 2,4-二硝基苯硫氯 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以83%的产率得到S,S-diphenyl-N-(2,4-dinitrophenylsulfenyl)-N'-tosylsulfodiimide
  参考文献：
  名称：

  Moderate generation of sulfenylnitrenes from novel N-sulfenylsulfodiimides

  摘要：

  N-Sulfenylated sulfodiimides were first prepared by the reaction of S,S-diphenyl-N-tosylsulfodiimide with arenesulfenyl chlorides under the basic conditions. Thermolysis of S,S-diphenyl-N-(2-nitrophenylsulfenyl)- and S,S-diphenyl-N-(2,4-dinitrophenylsulfenyl)sulfodiimides in the presence of olefins proceeded at 50-80 degrees C to give the corresponding deiminated S,S-diphenyl-N-tosylsulfimide and N-sulfenylaziridines in very good yields. 2,4-Dinitrophenyl-sulfenylnitrene was trapped by trans- and cis-l-phenylpropenes stereospecifically. The thermolysis temperature of the N-sulfenylsulfodiimides was found to be lower than N-sulfenylsulfoximide and higher than N-sulfenyliminosulfonium salt and very effective to trap the sulfenylnitrene to give the N-sulfenylaziridines in very good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.078

文献信息

• Moderate generation of sulfenylnitrenes from novel N-sulfenylsulfodiimides
  作者：Toshiaki Yoshimura、Tetsuo Fujie、Takayoshi Fujii

  DOI：10.1016/j.tetlet.2006.11.078

  日期：2007.1

  N-Sulfenylated sulfodiimides were first prepared by the reaction of S,S-diphenyl-N-tosylsulfodiimide with arenesulfenyl chlorides under the basic conditions. Thermolysis of S,S-diphenyl-N-(2-nitrophenylsulfenyl)- and S,S-diphenyl-N-(2,4-dinitrophenylsulfenyl)sulfodiimides in the presence of olefins proceeded at 50-80 degrees C to give the corresponding deiminated S,S-diphenyl-N-tosylsulfimide and N-sulfenylaziridines in very good yields. 2,4-Dinitrophenyl-sulfenylnitrene was trapped by trans- and cis-l-phenylpropenes stereospecifically. The thermolysis temperature of the N-sulfenylsulfodiimides was found to be lower than N-sulfenylsulfoximide and higher than N-sulfenyliminosulfonium salt and very effective to trap the sulfenylnitrene to give the N-sulfenylaziridines in very good yields. (c) 2006 Elsevier Ltd. All rights reserved.