hexa-p-tolyldistannane | 4158-75-2

• 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: hexa-p-tolyldistannane
• 英文别名: hexa(p-tolyl)ditin；Hexa-p-tolyl-distannan
• CAS: 4158-75-2
• 化学式: C₄₂H₄₂Sn₂
• 分子量: 784.215
• InChiKey: NWWIPYAGMQJOQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  44
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  hexa-p-tolyldistannane 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Krause; Becker, Chemische Berichte, 1920, vol. 53, p. 185 Anm. 1

  摘要：

  DOI：
• 作为产物：
  描述：

  三对甲苯基氯锡 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 以36%的产率得到hexa-p-tolyldistannane
  参考文献：
  名称：

  Wurtz-Type Reductive Coupling Reaction of Allyl Bromides and Haloorganotins in Cosolvent/H2O(NH4Cl)/Zn Media as a Route to Allylstannanes and Hexaaryldistannanes

  摘要：

  Twenty-one allylstannanes have been prepared via a simple Wurtz-type coupling reaction of allyl bromides and R3SnX compounds (R = Me, Et, Pr, Bu, Ph; X = Cl, I, OH), Bu2SnCl2, and (BU2SnCl)20 in cosolvent/H2O (NH4Cl saturated) media under the mediation of zinc powder. Also R3SnSnR3 compounds (R = Ph, p- and m-Tol) have been prepared via coupling of triaryltin chlorides. The stereochemical course of the reaction between R3SnCl and (C4H7)Br (C4H7 = alpha-methylallyl, trans- and cis-crotyl) has been extensively studied. Two distinct reactions are involved in the overall process: (i) the coupling reaction, which gives rise stereoselectively to the sole R3SnCH(CH3)CH=CH2 (alpha-isomer), and (ii) the subsequent isomerization of the alpha-isomer furnishing mixtures of (alpha, trans, cis)-isomers. The occurrence of reaction ii depends upon the nature either of the R group or the employed cosolvent. In cyclohexane, the alpha-isomer is exclusively obtained with R = Bu, while with R = Me, Et, and Pr it is found as a major component in the ternary isomeric mixture. In tetrahydrofuran, 2-propanol, acetonitrile, and pyridine, the isomerization occurs to an extent which depends on the polarity and the coordinating ability of the cosolvent itself. The observed stereoselection has been hypothesized to occur through one-electron transfer from the zinc metal to the (C4H7)Br to form stereoselectively an adsorbed CH2=CHCH(CH3)Br.-Zn.+ radical ion which is trapped by the R3SnCl reactant to form the alpha-isomer. Similarly, ditin compounds are thought to be formed by interaction of R3SnCl.-Zn.+ radical ions with R3SnCl molecules.

  DOI：

  10.1021/om00015a025

文献信息

• Electrosynthetic aspects of organotin compounds
  作者：Junzo Nokami、Hiroshi Nose、Rokuro Okawara

  DOI：10.1016/s0022-328x(00)85658-2

  日期：1981.6
• 572. Hexamethyl compounds of silicon, germanium, and tin
  作者：M. P. Brown、G. W. A. Fowles

  DOI：10.1039/jr9580002811

  日期：——
• Über gemischte Gruppe 14—Gruppe 14-Bindungen
  作者：Claudia Schneider、Martin Dräger

  DOI：10.1016/0022-328x(91)80135-7

  日期：1991.9

  p-Tol6PbSn has been synthesized by reaction of p-Tol3PbLi with p-Tol3SnI in THF/ether (1:2) at -78-degrees-C. The crystal structures of p-Tol4Pb (I4BAR) and of p-Tol6Sn2, p-Tol6PbSn and p-Tol6Pb2 have been determined. The three dinuclear compounds crystallize not strictly isomorphous. They exhibit the same space group (R3BAR) and rather similar unit cell dimensions. Yet according to the solvent of crystallization, two types with differing atomic position parameters can be distinguished ("homoeotypism with differences of parameters" in the definition of Laves). In both types, the individual molecules have a chiral C3-symmetric conformation and the non-chiral unit cell encloses both enantiomers. The metal-metal distances are Sn-Sn = 2.777(1), Pb-Sn = 2.813(2) and Pb-Pb = 2.851(1) angstrom. NMR (C-13, Sn-119, Pb-207) and Raman data are given (1J(Sn-119-Sn-119) = 4570, 1J(Sn-119-Pb-207) = 3640 Hz; nu (Sn-Sn) = 131, nu (Pb-Sn) = 114, nu (Pb-Pb) = 105 cm-1).
• Wurtz-Type Reductive Coupling Reaction of Allyl Bromides and Haloorganotins in Cosolvent/H2O(NH4Cl)/Zn Media as a Route to Allylstannanes and Hexaaryldistannanes
  作者：Friederike von Gyldenfeldt、Daniele Marton、Giuseppe Tagliavini

  DOI：10.1021/om00015a025

  日期：1994.3

  Twenty-one allylstannanes have been prepared via a simple Wurtz-type coupling reaction of allyl bromides and R3SnX compounds (R = Me, Et, Pr, Bu, Ph; X = Cl, I, OH), Bu2SnCl2, and (BU2SnCl)20 in cosolvent/H2O (NH4Cl saturated) media under the mediation of zinc powder. Also R3SnSnR3 compounds (R = Ph, p- and m-Tol) have been prepared via coupling of triaryltin chlorides. The stereochemical course of the reaction between R3SnCl and (C4H7)Br (C4H7 = alpha-methylallyl, trans- and cis-crotyl) has been extensively studied. Two distinct reactions are involved in the overall process: (i) the coupling reaction, which gives rise stereoselectively to the sole R3SnCH(CH3)CH=CH2 (alpha-isomer), and (ii) the subsequent isomerization of the alpha-isomer furnishing mixtures of (alpha, trans, cis)-isomers. The occurrence of reaction ii depends upon the nature either of the R group or the employed cosolvent. In cyclohexane, the alpha-isomer is exclusively obtained with R = Bu, while with R = Me, Et, and Pr it is found as a major component in the ternary isomeric mixture. In tetrahydrofuran, 2-propanol, acetonitrile, and pyridine, the isomerization occurs to an extent which depends on the polarity and the coordinating ability of the cosolvent itself. The observed stereoselection has been hypothesized to occur through one-electron transfer from the zinc metal to the (C4H7)Br to form stereoselectively an adsorbed CH2=CHCH(CH3)Br.-Zn.+ radical ion which is trapped by the R3SnCl reactant to form the alpha-isomer. Similarly, ditin compounds are thought to be formed by interaction of R3SnCl.-Zn.+ radical ions with R3SnCl molecules.
• Krause; Becker, Chemische Berichte, 1920, vol. 53, p. 185 Anm. 1
  作者：Krause、Becker

  DOI：——

  日期：——