E-(2-Iodoethenyl)oxirane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: E-(2-Iodoethenyl)oxirane
• 英文别名: 2-[(E)-2-iodoethenyl]oxirane
• 化学式: C₄H₅IO
• 分子量: 195.988
• InChiKey: IDSIUFTZQRZSBV-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3-环氧丙醛 、 iodomethylenetriphenylphosphorane 在 六甲基磷酰三胺 作用下， 生成 Z-(2-Iodoethenyl)oxirane 、 E-(2-Iodoethenyl)oxirane
  参考文献：
  名称：

  Free-radical homolytic substitution at selenium: an efficient method for the preparation of selenophenes

  摘要：

  Substituted and unsubstituted 1-(benzylseleno)-4-iodobut-3-en-2-ols 12 and 2-(benzylseleno)-1-(2-iodophenyl)ethanols 18 react smoothly with tris(trimethylsilyl)silane in benzene at 80-degrees-C (AIBN initiator) to afford selenophenes 16 and benzoselenophenes 21 in excellent yield. These reactions presumably involve intramolecular homolytic substitution by aryl and vinyl radicals 14 and 20 at the selenium atom with the expulsion of benzyl radical followed by facile dehydration to afford the aromatic selenophene ring system in each case. Competitive rate studies on the ring closure of the 2-[2-(benzylseleno)ethyl]phenyl radical 25 in the presence of tri-n-butyltin hydride to give 2,3-dihydrobenzo[b]selenophene (27) and 1-(benzylseleno)-2-phenylethane (28) provide a rate constant for ring closure (k(c)) of approximately 3 X 10(7) s-1 at 80-degrees-C. The determination of more accurate data is hampered by what we attribute to be the involvement of a slow, but competive nonradical process.

  DOI：

  10.1021/jo00073a021

文献信息

• Free-radical homolytic substitution at selenium: an efficient method for the preparation of selenophenes
  作者：Jennifer E. Lyons、Carl H. Schiesser、Katarina Sutej

  DOI：10.1021/jo00073a021

  日期：1993.10

  Substituted and unsubstituted 1-(benzylseleno)-4-iodobut-3-en-2-ols 12 and 2-(benzylseleno)-1-(2-iodophenyl)ethanols 18 react smoothly with tris(trimethylsilyl)silane in benzene at 80-degrees-C (AIBN initiator) to afford selenophenes 16 and benzoselenophenes 21 in excellent yield. These reactions presumably involve intramolecular homolytic substitution by aryl and vinyl radicals 14 and 20 at the selenium atom with the expulsion of benzyl radical followed by facile dehydration to afford the aromatic selenophene ring system in each case. Competitive rate studies on the ring closure of the 2-[2-(benzylseleno)ethyl]phenyl radical 25 in the presence of tri-n-butyltin hydride to give 2,3-dihydrobenzo[b]selenophene (27) and 1-(benzylseleno)-2-phenylethane (28) provide a rate constant for ring closure (k(c)) of approximately 3 X 10(7) s-1 at 80-degrees-C. The determination of more accurate data is hampered by what we attribute to be the involvement of a slow, but competive nonradical process.