n-propyl chlorosulfite | 22598-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: n-propyl chlorosulfite
• 英文别名: n-Propylchlorsulfit；Propyl-chlorsulfit；1-chlorosulfinyloxypropane
• CAS: 22598-38-5
• 化学式: C₃H₇ClO₂S
• 分子量: 142.606
• InChiKey: XHPBLHAZMLPNTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 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：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  n-propyl chlorosulfite 以 丙酮 为溶剂， 生成 1-氯丙烷
  参考文献：
  名称：

  Reinvestigation of the SNi reaction. The ionization of chlorosulfites

  摘要：

  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.

  DOI：

  10.1021/jo00062a028
• 作为产物：
  描述：

  原甲酸三丙酯 在 氯化亚砜 作用下， 生成 n-propyl chlorosulfite
  参考文献：
  名称：

  Levaillant, Annales de Chimie (Cachan, France), 1936, vol. <11>6, p. 524,525

  摘要：

  DOI：

文献信息

• A CONVENIENT PREPARATION OF SULPHINIC ESTERS FROM SULPHINYL CHLORIDES AND CHLOROSULPHITES USING HEXAMETHYLDISILOXANE AS CHLORIDE ANION ACCEPTOR
  作者：Jozef Drabowicz

  DOI：10.1246/cl.1981.1753

  日期：1981.12.5

  Sulphinic esters can be obtained in high yields by the reaction of sulphinyl chlorides with chlorosulphites in the presence of hexamethyldisiloxane and catalytic amount of dimethyl sulphoxide.

  在六甲基二硅氧烷和催化量的二甲基亚砜存在下，通过亚磺酰氯与亚硫酸氢盐的反应，可以高产率地获得亚磺酸酯。
• Gerrard, Journal of the Chemical Society, 1940, p. 228
  作者：Gerrard

  DOI：——

  日期：——
• Stable carbocations. CLXIII. Complexing ionization, and fragmentative alkylcarbenium ion formation from alkyl haloformates, thiolhaloformates, and halosulfites with antimony pentafluoride
  作者：George A. Olah、Peter Schilling、J. Martin Bollinger、Jun Nishimura

  DOI：10.1021/ja00814a036

  日期：1974.4
• Seel,F. et al., Chemische Berichte, 1969, vol. 102, p. 443 - 448
  作者：Seel,F. et al.

  DOI：——

  日期：——
• ZINNER; KOELLING, Archiv der Pharmazie, 1961, vol. 294 /66, p. 284 - 291
  作者：ZINNER、KOELLING

  DOI：——

  日期：——