2,4,6-Tri-tert-butylbenzeneselenenyl bromide | 114031-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,6-Tri-tert-butylbenzeneselenenyl bromide
• 英文别名: (2,4,6-Tritert-butylphenyl) selenohypobromite
• CAS: 114031-59-3
• 化学式: C₁₈H₂₉BrSe
• 分子量: 404.292
• InChiKey: KYRUQJQVDXXUDS-UHFFFAOYSA-N

物化性质

• 沸点：
  347.3±41.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,4,6-Tri-tert-butylbenzeneselenenyl bromide 在 水 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 生成 2,4,6-tri-tert-butylbenzeneseleninic acid
  参考文献：
  名称：

  Organoselenium chemistry. Preparation and reactions of 2,4,6-tri-tert-butylbenzeneselenenic acid

  摘要：

  DOI：

  10.1021/jo00245a056
• 作为产物：
  描述：

  1-溴-2,4,6-三叔丁基苯 、 正丁基锂 以68%的产率得到
  参考文献：
  名称：

  REICH, HANS J.;JASPERSE, GRAIG P., J. ORG. CHEM., 53,(1988) N 10, 2389-2390

  摘要：

  DOI：

文献信息

• The markedly enhanced basicity of selenenamides vs sulfenamides and the mechanism of the methanolysis of o-nitro- and 2,4,6-tri-tert-butylbenzeneselenenamides
  作者：John L. Kice、Andrei G. Kutateladze

  DOI：10.1021/jo00056a026

  日期：1993.2

  Measurement in acetonitrile-methanol of the basicity of selenenamides shows that they are approximately 3 pK units more basic than the corresponding sulfenamides. Since other explanations do not seem tenable, this apparently results from the fact that selenium is less electronegative than sulfur, although it is somewhat surprising that the small difference in the electronegativity of the two elements should lead to such a large difference in basicity. In the same solvent the kinetics of the acid-catalyzed methanolyses (eq 2) of o-nitro- and 2,4,6-tri-tert-butylbenzeneselenenamides are similar (large dependence of rate on [MeOH], unusual dependence of rate on [H+]) to those for the methanolysis of the corresponding o-nitrobenzenesulfenamides. In the latter case the kinetics have been shown6 to be indicative of a mechanism where a sulfuranide (3, eq 5) is the key intermediate on the reaction coordinate; as a consequence, a similar kind of mechanism (eq 6) involving a hypervalent selenium intermediate (4) is proposed for eq 2. The unusual dependence on [H+] is because acid-catalyzed reversion of 4 to protonated selenenamide (2-H+) and methanol (step k-6) is faster under certain conditions than cleavage of 4 to give the final products (step k7). COMParison of the methanolysis kinetics of o-nitro (2a) and 2,4,6-tri-tert-butylbenzeneselenenamides (2c) shows that the coordination of an o-nitro group to selenium that stabilizes 2a and 2a-H+ does not appear to change the mechanism for methanolysis although it does cause the partitioning of 4 (k-6[H+]/k7) to be much less favorable to the formation of products (step k7).
• REICH, HANS J.;JASPERSE, GRAIG P., J. ORG. CHEM., 53,(1988) N 10, 2389-2390
  作者：REICH, HANS J.、JASPERSE, GRAIG P.

  DOI：——

  日期：——
• Organoselenium chemistry. Preparation and reactions of 2,4,6-tri-tert-butylbenzeneselenenic acid
  作者：Hans J. Reich、Craig P. Jasperse

  DOI：10.1021/jo00245a056

  日期：1988.5