1-apocamphanyl chlorosulfite | 24560-28-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-apocamphanyl chlorosulfite
• 英文别名: 1-Chlorsulfinyloxy-apocamphan；1-Chlorosulfinyl-apocamphan；1-Chlorosulfinyloxy-7,7-dimethylbicyclo[2.2.1]heptane；1-chlorosulfinyloxy-7,7-dimethylbicyclo[2.2.1]heptane
• CAS: 24560-28-9
• 化学式: C₉H₁₅ClO₂S
• 分子量: 222.736
• InChiKey: FSAIZNFTIMHZEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-apocamphanyl chlorosulfite 在 silver tetrafluoroborate 、 1,1,3,3-四甲基脲 作用下， 以 氯苯 为溶剂， 生成 Apocamphyl-(1)-fluorid
  参考文献：
  名称：

  Reactions of chloroformates with silver fluoro salts

  摘要：

  DOI：

  10.1021/ja01046a023
• 作为产物：
  描述：

  1-Apocamphancarbonsaeure 在 氯化亚砜 、 硫酸 、 双氧水 作用下， 反应 8.0h， 生成 1-apocamphanyl chlorosulfite
  参考文献：
  名称：

  Reactions of chloroformates with silver fluoro salts

  摘要：

  DOI：

  10.1021/ja01046a023

文献信息

• Reinvestigation of the SNi reaction. The ionization of chlorosulfites
  作者：Peter R. Schreiner、Paul v. R. Schleyer、Richard K. Hill

  DOI：10.1021/jo00062a028

  日期：1993.5

  The decomposition of alkyl chlorosulfites (ROSOCl) has been investigated both computationally and experimentally. Semiempirical (AM1 and PM3) as well as ab initio (HF/3-21G(*), HF/6-31G*, and MP2(full)/6-31G*//MP2(full)/6-31G*) methods were employed, and the results were confirmed experimentally by NMR spectroscopy. The computations indicated that certain alkyl sulfinyl cations (ROSO+) are stable and might be involved in the decomposition of chlorosulfites. Detection of these ions by H-1 and C-13 NMR spectroscopy in polar solvents such as acetone-d6 and acetonitrile-d3 as well as kinetic studies allowed important conclusions to be drawn about the mechanistic details of the S(N)i reaction. We conclude that primary alkyl chlorosulfites ionize to yield a sulfinyl cation (ROSO+) and Cl-, whereas tertiary chlorosulfites preferentially give a carbenium ion and a chlorosulfinyl anion (OSOCl-). The generation of these ion pairs is facilitated in polar solvents where the rates of decomposition of chlorosulfites are largely accelerated. The decomposition of neopentyl chlorosulfite without rearrangement and the substitution at the bridgehead position of 7,7-dimethylbicyclo[2.2.1]-heptyl 1-chlorosulfite show that the loss Of SO2 from ROSO+ must be accompanied by the attack of the chloride ion from the front side.
• Reactions of chloroformates with silver fluoro salts
  作者：Peter Beak、Ronald J. Trancik、David A. Simpson

  DOI：10.1021/ja01046a023

  日期：1969.8