2-butyl chlorosulfite | 22598-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-butyl chlorosulfite
• 英文别名: chlorosulfurous acid sec-butyl ester；(+/-)-chlorosulfurous acid sec-butyl ester；(+/-)-Chloroschwefligsaeure-sec-butylester；Chlorsulfinsaeure-(+/-)-sec-butylester；Chlorsulfinsaeure-(+/-)-sek.-butylester；sek.-Butyl-chlorsulfinat
• CAS: 22598-58-9；55954-47-7
• 化学式: C₄H₉ClO₂S
• 分子量: 156.633
• InChiKey: CKDSOFWJKGVNPN-UHFFFAOYSA-N

物化性质

• 沸点：
  75-77 °C
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  8.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-butyl chlorosulfite 在 O₂S*KF 作用下， 生成 fluorosulfurous acid sec-butyl ester
  参考文献：
  名称：

  Seel,F. et al., Chemische Berichte, 1969, vol. 102, p. 443 - 448

  摘要：

  DOI：
• 作为产物：
  描述：

  仲丁氧基三甲基硅烷 在 氯化亚砜 作用下， 生成 2-butyl chlorosulfite
  参考文献：
  名称：

  Currell,B.R. et al., Journal of the Chemical Society, 1960, p. 2776 - 2778

  摘要：

  DOI：

文献信息

• 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
• The Kinetics and Stereochemistry of the Decomposition of Secondary Alkyl Chlorosulfites¹
  作者：Edward S. Lewis、Charles E. Boozer

  DOI：10.1021/ja01122a005

  日期：1952.1
• Carre; Libermann, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1933, vol. 196, p. 1419
  作者：Carre、Libermann

  DOI：——

  日期：——
• 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.