2-Bromo-2-(2,2,2-trichloroethyl)adamantane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 2-Bromo-2-(2,2,2-trichloroethyl)adamantane
• 化学式: C₁₂H₁₆BrCl₃
• 分子量: 346.522
• InChiKey: RBEYJINGMWJWOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-亚甲基金刚烷 、 三氯溴甲烷 生成 2-Bromo-2-(2,2,2-trichloroethyl)adamantane
  参考文献：
  名称：

  BODEPUDI, VANI R.;IE, NOBLE WILLIAM J., J. ORG. CHEM., 56,(1991) N, C. 2001-2006

  摘要：

  DOI：

文献信息

• Electronic control of face selection in the capture of radicals
  作者：Vani R. Bodepudi、William J. Le Noble

  DOI：10.1021/jo00006a009

  日期：1991.3

  A simple procedure is described which leads to the pure epimeric 2-(5-phenyl)adamantanecarboxylic acids E-1 and Z-1. Both acids upon treatment with bromine and mercuric oxide in carbon tetrachloride undergo the Hunsdiecker reaction to give the same mixture of E- and Z- 2-bromo-5-phenyladamantanes 4. 5-Phenyl-2-methyleneadamantane 6 undergoes reaction with bromotrichloromethane to give two diastereomeric adducts. In both instances, the major isomer results from the abstraction of a bromine atom by the zu face of the intermediate 5-phenyl-2-adamantyl radicals. The results mesh with other examples of face selection which we have previously ascribed to transition-state hyperconjugation. An additional case (hydride shift in a carbocation) was encountered in this work, as well as one apparent exception: the oxirane formation from adamantanone and sulfonium ylids. That result is attributed to thermodynamic control of the initial addition step.