7'-(7-bromo-7-norbornyl)-7'-bromonorbornane | 51689-33-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 7'-(7-bromo-7-norbornyl)-7'-bromonorbornane
• CAS: 51689-33-9
• 化学式: C₁₄H₂₀Br₂
• 分子量: 348.121
• InChiKey: QNBBKXHJWGATOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  7-norbornylidene-7-norbornane 在 溴 、 溶剂黄146 作用下， 生成 7'-(7-bromo-7-norbornyl)-7'-bromonorbornane
  参考文献：
  名称：

  Electrophilic Bromination of 7-Norbornylidene-7'-Norbornane. The Observation of an Unusually Large Inverse Deuterium Kinetic Isotope Effect

  摘要：

  The bromination of 7-norbornylidene-7'-norbornane (1) and its perdeuterated analogue (2) was studied in HOAc and MeOH by investigating the reaction kinetics and product distributions as a function of added [Br-]. In all cases there is a significant inverse deuterium kinetic isotope effect on the bromination rate constant (k(g)) which, in HOAc, is k(g)(2/1) 1.56 and 1.83 at [Br-] = 0 and 0.04 M, respectively. Added Br- causes a significant rate retardation which indicates the intervention of a reversibly formed bromonium ion intermediate. Product studies indicate the formation of four products, a normal dibromide and beta-bromo solvate and two that arise from capture of an alpha-bromo cation formed from a Wagner-Meerwein rearrangement of the first-formed bromonium ion. In HOAc, added [Br-] leads to an increase in the amount of the normal dibromide at the expense of the solvent-incorporated and rearranged products. In MeOH, dibromide is never an important product at any [Br-] investigated, the two major isolated products being the normal methoxy bromide and rearranged ketone. Quantitative analyses of the products formed from bromination of 1 and 2 in HOAc as a function of [Br-] indicate little difference in the product partitioning that is attributable to the presence of H or D. A unified mechanism that accommodates all the data is presented.

  DOI：

  10.1021/ja00139a009

文献信息

• Nagorski; Ślebocka-Tilk; Brown, Journal of the American Chemical Society, 1994, vol. 116, # 1, p. 419 - 420
  作者：Nagorski、Ślebocka-Tilk、Brown

  DOI：——

  日期：——