1-deutero-2,2-dimethylhexane

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 英文名称: 1-deutero-2,2-dimethylhexane
• 英文别名: 1-deuterio-2,2-dimethylhexane
• 化学式: C₈H₁₈
• 分子量: 115.223
• InChiKey: FLTJDUOFAQWHDF-VMNATFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• 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：

  1-iodo-2,2-dimethylhexane 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 2,2-二甲基己烷 、 1-deutero-2,2-dimethylhexane
  参考文献：
  名称：

  Convincing Evidence, Not Involving Cyclizable Radical Probes, That the Reaction of LiAlH₄ with Hindered Alkyl Iodides Proceeds Predominantly by a Single Electron Transfer Pathway^,

  摘要：

  Previous workers have maintained that evidence for the radical nature of the reaction of LiAlH4 with sterically hindered alkyl iodides is due to radical initiation by impurities followed by a halogen atom radical chain process involving the cyclizable alkyl iodide probe and that the reduction of the C-I bond actually proceeds by an S(N)2 pathway. In order to resolve the validity of this explanation, 1-iodo-2,2-dimethylhexane (the saturated counterpart of the cyclizable probe), which is not capable of this halogen atom radical chain process, was allowed to react with LiAlD4. The reduction product, 2,2-dimethylhexane, contained only 4-76% deuterium depending on the conditions of the reaction. This result is consistent with the reaction proceeding by a SET process via a radical intermediate and is inconsistent with an S(N)2 pathway. We have determined the influence of the nature of the reaction on the type of reactor surface (Pyrex, Teflon, stainless steel, and quartz) used in the reaction. We have also studied the influence of AlD3 (a byproduct in the reduction) in the mechanistic evaluation of this reaction.

  DOI：

  10.1021/jo961651+

文献信息

• Single electron transfer in the reaction of an alkyl iodide with LiAlH4 and LiAlD4 in the absence of a halogen atom radical chain process
  作者：E.C. Ashby、Catherine O. Welder、Fabio Doctorovich

  DOI：10.1016/s0040-4039(00)79296-3

  日期：1993.11

  Reactions of the noncyclizable alkyl iodide, 1-iodo-2,2-dimethylhexane (9), with LiAlH4 and LiAlD4 have been carried out under a variety of conditions. Although the structure of 9 prohibits a halogen atom radical chain process, deuterium incorporation studies provide convincing evidence for single electron transfer (SET) as the major reaction pathway.

  所述noncyclizable烷基碘的反应中，1-碘-2,2-二甲基己烷（9）中，用的LiAlH 4和LiAlD 4已经在各种条件下进行。尽管9的结构禁止卤素原子自由基链过程，但氘掺入研究为单电子转移（SET）作为主要反应途径提供了令人信服的证据。
• The effect of reactor surfaces on single electron transfer reactions. The reaction of 1-Iodo-2,2-dimethylhexane with lithium aluminum deuteride
  作者：E.C. Ashby、Catherine O. Welder

  DOI：10.1016/0040-4039(95)01486-2

  日期：1995.10

  reactor plays a role in the product distribution. However, treated pyrex, new pyrex and quartz vessels yield consistent data that support single electron transfer as the major reaction pathway in the reduction of 4 with LiAlD4.

  1-碘-2，2-二甲基己烷（4）与LiAlD 4的反应已经在各种反应容器中进行。在用过的派热克斯玻璃纤维，聚四氟乙烯和不锈钢制成的容器中，反应器的表面在产物分布中起作用。但是，经过处理的派热克斯玻璃，新的派热克斯玻璃和石英容器产生的数据一致，支持单电子转移，这是LiAlD 4还原4中的主要反应途径。
• Convincing Evidence, Not Involving Cyclizable Radical Probes, That the Reaction of LiAlH₄ with Hindered Alkyl Iodides Proceeds Predominantly by a Single Electron Transfer Pathway^,
  作者：E. C. Ashby、Catherine O. Welder

  DOI：10.1021/jo961651+

  日期：1997.5.1

  Previous workers have maintained that evidence for the radical nature of the reaction of LiAlH4 with sterically hindered alkyl iodides is due to radical initiation by impurities followed by a halogen atom radical chain process involving the cyclizable alkyl iodide probe and that the reduction of the C-I bond actually proceeds by an S(N)2 pathway. In order to resolve the validity of this explanation, 1-iodo-2,2-dimethylhexane (the saturated counterpart of the cyclizable probe), which is not capable of this halogen atom radical chain process, was allowed to react with LiAlD4. The reduction product, 2,2-dimethylhexane, contained only 4-76% deuterium depending on the conditions of the reaction. This result is consistent with the reaction proceeding by a SET process via a radical intermediate and is inconsistent with an S(N)2 pathway. We have determined the influence of the nature of the reaction on the type of reactor surface (Pyrex, Teflon, stainless steel, and quartz) used in the reaction. We have also studied the influence of AlD3 (a byproduct in the reduction) in the mechanistic evaluation of this reaction.