(tert-butyl)(bromo)(phenyl)phosphine | 93634-81-2

• 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: (tert-butyl)(bromo)(phenyl)phosphine
• 英文别名: Bromo-tert-butyl-phenylphosphane
• CAS: 93634-81-2
• 化学式: C₁₀H₁₄BrP
• 分子量: 245.099
• InChiKey: YKRAPNSFMLGCJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  叔丁基苯基膦 在 正丁基锂 、 9-溴芴 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以78%的产率得到(tert-butyl)(bromo)(phenyl)phosphine
  参考文献：
  名称：

  New Look into the Synthesis of Polyhalogenoarylphosphanes

  摘要：

  The present study shows new aspects of the synthesis of polyhalogenoarylphosphanes. The sterically hindered anions Ph(R)P-Y(-) (1a-c, Y = O, lone pair; R = Ph, Bu(t)) have been used to show the complexity of the reaction between phosphorus nucleophiles and hexahalogenobenzenes or 9-bromofluorene (E3). The Ph(Bu(t))P-O(-)(1a) anion reacts with hexachlorobenzene (E1), hexafluorobenzene (E2), or E3 to give Ph(R)P(O)X (4a-c, X = F, Cl, Br) with the release of the corresponding carbanion as a nucleofuge, followed by side reactions. In contrast, the lithium phosphides Ph(R)PLi (1b, c) react with hexahalogenobenzenes to give the corresponding diphosphanes 5a,b as the main product and traces of P-arylated products, i.e., Ph(R)P-C(6)X(5) (10a,b, X = Cl, F). Unexpectedly, Ph(Bu(t))PLi (1b) reacts with an excess of 9-bromofluorene to give only halogenophosphane Ph(Bu(t))P-X.

  DOI：

  10.1080/10426500802531677

文献信息

• New Look into the Synthesis of Polyhalogenoarylphosphanes
  作者：Jacek E. Nycz

  DOI：10.1080/10426500802531677

  日期：2009.10.13

  The present study shows new aspects of the synthesis of polyhalogenoarylphosphanes. The sterically hindered anions Ph(R)P-Y(-) (1a-c, Y = O, lone pair; R = Ph, Bu(t)) have been used to show the complexity of the reaction between phosphorus nucleophiles and hexahalogenobenzenes or 9-bromofluorene (E3). The Ph(Bu(t))P-O(-)(1a) anion reacts with hexachlorobenzene (E1), hexafluorobenzene (E2), or E3 to give Ph(R)P(O)X (4a-c, X = F, Cl, Br) with the release of the corresponding carbanion as a nucleofuge, followed by side reactions. In contrast, the lithium phosphides Ph(R)PLi (1b, c) react with hexahalogenobenzenes to give the corresponding diphosphanes 5a,b as the main product and traces of P-arylated products, i.e., Ph(R)P-C(6)X(5) (10a,b, X = Cl, F). Unexpectedly, Ph(Bu(t))PLi (1b) reacts with an excess of 9-bromofluorene to give only halogenophosphane Ph(Bu(t))P-X.