selenium(II) bis(2-methyl-2-propanethiolate) | 75272-63-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代硒化物
• 英文名称: selenium(II) bis(2-methyl-2-propanethiolate)
• 英文别名: SeS-(1,1-Dimethylethyl) 2-methyl-2-propanesulfeno(selenothioperoxoate)；2-tert-butylsulfanylselanylsulfanyl-2-methylpropane
• CAS: 75272-63-8
• 化学式: C₈H₁₈S₂Se
• 分子量: 257.323
• InChiKey: ILPAGRNJKILHGH-UHFFFAOYSA-N

物化性质

• 沸点：
  282.4±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  selenium(II) bis(2-methyl-2-propanethiolate) 在 三苯基膦 作用下， 生成 叔丁基二硫
  参考文献：
  名称：

  通过硒转移试剂制备二硫硒硒

  摘要：

  在独特的硒转移试剂双唑硒化物4中添加两摩尔硫醇可得到非常好的二硫代硒化物（RS-Se-SR）分离产率。

  DOI：

  10.1016/s0040-4039(97)10383-5
• 作为产物：
  描述：

  2-tert-butylsulfanylselanyloxysulfanyl-2-methylpropane 以72%的产率得到
  参考文献：
  名称：

  KICE, JOHN L.;WILSON, DEAN M.;ESPINOLA, JOHN M., J. ORG. CHEM., 56,(1991) N1, C. 3520-3524

  摘要：

  DOI：

文献信息

• Reactivity of nucleophiles toward and the site of nucleophilic attack on bis(alkylthio) selenides
  作者：John L. Kice、Henryka Slebocka-Tilk

  DOI：10.1021/ja00389a039

  日期：1982.12
• Oxidation of bis(tert-butylthio) selenide at low temperatures: search for a bis(alkylthio) selenoxide
  作者：John L. Kice、Dean M. Wilson、John M. Espinola

  DOI：10.1021/jo00011a015

  日期：1991.5

  Oxidation of bis(tert-butylthio) selenide, t-BuSSeSBu-t (1a), by peracetic acid at -40-degrees-C leads to a monooxidation product (1a-O) whose H-1 (two singlets) and C-13 NMR spectra (four resonances) show that the two tert-butyl groups in 1a-O are magnetically nonequivalent. It cannot therefore be the bis(alkylthio) selenoxide, t-BuSSe(O)SBu-t (3a), and is either t-BuS(O)SeSBu-t, 5a (oxidation of 1a at S rather than Se), or t-BuSSeOSBu-t, 4a (formed by rapid isomerization of initially formed 3a). The fact that delta Se-77 for 1a-O is 289 ppm downfield from delta Se-77 for 1a is inconsistent with structure 5a and indicates that 1a-O has structure 4a, t-BuSSeOSBu-t. Reaction of t-BuSH with 1a-O gives 1a plus t-BuSOH, in accord with what would be expected for nucleophilic attack of the thiol on the selenium of 4a. While oxidation of 1a by peracid is thought to result initially in 3a, this thioselenoxide apparently isomerizes to 4a so rapidly, even at -40-degrees-C, that 4a is the first oxidation product detectable by NMR. These results are of significance with regard to several steps in the previously proposed (ref 4) mechanism (Scheme I) for the formation of bis(alkylthio) selenides from the reaction of thiols with selenite.
• Mechanism of the reaction of thiols with selenite
  作者：John L. Kice、Thomas W. S. Lee、Shu-Teh Pan

  DOI：10.1021/ja00533a025

  日期：1980.6