2,2-dicyanovinyl iodide | 97056-15-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2,2-dicyanovinyl iodide
• 英文别名: 2-(iodomethylidene)propanedinitrile
• CAS: 97056-15-0
• 化学式: C₄HIN₂
• 分子量: 203.97
• InChiKey: YZAFWRQLZXCONG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯-1,3-丁二烯 、 2,2-dicyanovinyl iodide 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以46%的产率得到4,4-dicyano-5-iodo-3-phenylcyclohex-1-ene
  参考文献：
  名称：

  Spontaneous homopolymerization competes with Diels-Alder cycloaddition of 1-aryl-1,3-butadienes to dienophiles containing a leaving group

  摘要：

  The competition between Diels-Alder cycloaddition and spontaneous concurrent polymerization was investigated in the reactions of 1-phenyl-1,3-butadiene (1) and 1-p-anisyl-1,3-butadiene (2) with electrophilic olefins. The reactions of 1 and 2 with electrophilic olefins trisubstituted with cyano and/or carbomethoxy groups gave only concerted [4 + 2] cycloaddition products. However, when olefins with a leaving group in the beta-position were allowed to react with 1 and 2, cationic homopolymerization of the 1-arylbutadiene competed with the concerted cycloaddition. More polymer was formed with increased electrophilic character of the olefin and with better leaving groups. Formation of a 2-hexene-1,6-zwitterionic intermediate from the s-trans diene and the olefin, which can undergo elimination of the leaving group, is postulated. The resulting carbocation can then initiate cationic homopolymerization.

  DOI：

  10.1021/jo00051a031