bis(diphenylfluorostannyl)methane | 164527-15-5

• 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: bis(diphenylfluorostannyl)methane
• 英文别名: (Ph2FSn)2CH2；Ph2FSn(CH2)SnFPh2；Methylenebis[fluoro(diphenyl)stannane]；fluoro-[[fluoro(diphenyl)stannyl]methyl]-diphenylstannane
• CAS: 164527-15-5
• 化学式: C₂₅H₂₂F₂Sn₂
• 分子量: 597.866
• InChiKey: IREKNBXGLPXWKR-UHFFFAOYSA-L

物化性质

• 沸点：
  516.2±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(diphenylfluorostannyl)methane 在 Mg 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 生成 bis[((diphenylfluorostannyl)methyl)phenylfluorostannyl]methane
  参考文献：
  名称：

  亚甲基桥连的三和四丁酸酯化合物，路易斯酸

  摘要：

  一系列三核锡化合物（Ph 2 XSnCH 2）2 SnXPh（2，X = Ph; 6，X = F; 8，X = Cl）和（PhCl 2 SnCH 2）2 SnCl 2（10）的合成报道了四核锡化合物（Ph 2 XSnCH 2 SnXPh）2 CH 2（3，X = Ph; 7，X = F; 9，X = Cl），[[（Ph 2 FSnCH 2）2 SnFPh· F] -描述了[C 12 H 24 O 6 ·K] +（6b）。可变温度119 Sn和19 F NMR研究表明，观察到的6b固态阴离子的结构保留在溶液中。尽管在电喷雾质谱（ESMS）的乙腈溶液中发现了这类物质，但没有NMR证据表明与氟离子形成1：2加合物。119 Sn NMR光谱数据表明三核锡化合物8与[（Ph 3 P）2 N] + Cl-的反应。HMPA形成1：1络合物[（Ph 2 ClSnCH 2）2 SnClPh·Cl] - [（Ph

  DOI：

  10.1021/om970537u
• 作为产物：
  描述：

  potassium fluoride 、 bis(bromodiphenylstannyl)methane 以 水 、 丙酮 为溶剂， 以92%的产率得到bis(diphenylfluorostannyl)methane
  参考文献：
  名称：

  Bis(halodiphenylstannyl)alkanes as Bidentate Lewis Acids toward Halide Ions

  摘要：

  Sn-119 and F-19 NMR spectroscopies were used to study reaction of bis(halodiphenylstannyl)alkanes (Ph(2)XSn)(2)(CH2)(n) (X = F, Cl, Br, I; n = 1, 2, 3) with various halide ions in dichloromethane solution. Ah three series of bis(halodiphenylstannyl)alkanes, (Ph(2)XSn)(2)-(CH2)(n) (X = F, Cl, Br, I; n = 1, 2, 3), exhibit chelate ability toward halide, forming anionic 1:1 adducts [(Ph(2)XSn)(2)(CH2)(n)X](-) which are static at -100 degrees C on the NMR time scale. The bis(halodiphenystannyl) alkanes always preferentially chelate fluoride ion over chloride or bromide. Endocyclic Sn-CH2 rotation brings about intramolecular exchange between bridging and terminal fluorine atoms at higher temperature. For n = 1, and 1:1 adducts [(Ph(2)XSn)(2)(CH2)X](-) react with additional fluoride (but not chloride or bromide) eventually to give [(Ph(2)F(2)Sn)(2)(CH2)(2)](2-) in which both tin atoms are five-coordinated. For n = 2, the 1:1 adducts [(Ph(2)XSn)(2)(CH2)(2)X](-) appear particularly stable and there is no evidence for formation of 1:2 adducts [(Ph(2)X(2)Sn)(2)(CH2)(2)](2-). Propylene-bridged 1:1 adducts, [(Ph(2)XSn)(2)(CH2)(3)X](-), react with both fluoride and chloride to give 1:2 adducts, [(Ph(2)F(2)Sn)(2)(CH2)(3)](2-) and [(Ph(2)Cl(2)Sn)(2)(CH2)(3)](2-), respectively, in which the tin atoms remain five-coordinated. The crystal structures of [(Ph(2)FSn)(2)CH2F](-) (1), [(Ph(2)BrSn)(2)CH2F](-) (4), [(Ph(2)ISn)(2)CH2F](-) (8), and [(Ph(2)ClSnCH(2))(2)F](-) (11), as their tetraethylammonium salts (la, 4a, 8a, and 11a, respectively), are described. Colorless crystals of la are monoclinic, space group P2(1)/n, with a = 11.695(4) Angstrom, b = 14.667(2) Angstrom, c = 18.956(2) Angstrom, beta = 103.33(1)degrees, V = 3164(1) Angstrom(3) and Z = 4. Colorless crystals of 4a are monoclinic, space group Cc with a = 11.758(1) Angstrom, b = 14.880(2) Angstrom, c = 19.316(2) Angstrom, beta = 93.981(9)degrees, V = 3371.3(6) Angstrom(3), and Z = 4. Colorless crystals of 8a are monoclinic, space group P2(1)/n, with a = 10.032(1) Angstrom, b = 16.993(3) Angstrom, c = 20.523(3) Angstrom, beta = 99.65(1)degrees, V = 3434.9(8) Angstrom(3), and Z = 4, Colorless crystals of 11a are monoclinic, space group P2(1), with a = 9.562(2) Angstrom, b = 15.529(4) Angstrom, c = 11.359(4) Angstrom, beta = 95.51(2)degrees, V = 1678.9(9) Angstrom(3), and Z = 2. The structures were refined to final R = 0.027, 0.029, 0.033, and 0.029 for 4661, 2647, 3843, and 3457 reflections with I greater than or equal to 3.0 sigma(I), respectively.

  DOI：

  10.1021/om00005a057

文献信息

• Novel 10- and 20-Membered Tin- and Silicon-Containing Rings:  Synthesis, Complexation Behavior, and Conversion into a Lewis Acidic Polymer^,
  作者：Marcus Schulte、Giuseppina Gabriele、Markus Schürmann、Klaus Jurkschat、Andrew Duthie、Dainis Dakternieks

  DOI：10.1021/om020740b

  日期：2003.1.1

  Reaction of the dimethylsilylmethyl-substituted tetraorganotin derivative CH2[CH2Sn(Ph2)CH2Si(H)Me2]2 (1) and CH2[CH2Sn(Ph2)CH2Si(i-PrO)Me2]2 (3), respectively, with mercuric chloride afforded the novel silicon- and tin-containing 10- and 20-membered rings cyclo-CH2[CH2Sn(Cl2)CH2Si(Me2)]2O (4) and cyclo-CH2[CH2Sn(Cl2)CH2Si(Me2)OSi(Me2)CH2Sn(Cl2)CH2]2CH2 (5). Both compounds 4 and 5 can be converted

  二甲基甲硅烷基甲基取代的四有机锡衍生物CH 2 [CH 2 Sn（Ph 2）CH 2 Si（H）Me 2 ] 2（1）与CH 2 [CH 2 Sn（Ph 2）CH 2 Si（i -PrO）的反应Me 2 ] 2（3）分别与氯化汞反应得到新型的含硅和锡的10和20元环-CH 2 [CH 2 Sn（Cl 2）CH 2 Si（Me 2）]2 O（4）和环-CH 2 [CH 2 Sn（Cl 2）CH 2 Si（Me 2）OSi（Me 2）CH 2 Sn（Cl 2）CH 2 ] 2 CH 2（5）。化合物4和5均可转化为可溶的路易斯酸性聚合物聚-[Si（Me 2）CH 2 Sn（Cl 2）（CH 2）3 Sn（Cl 2）CH 2 Si（Me 2）O]（8）。119 Sn NMR研究表明4作为氯离子的双齿路易斯酸，仅形成1：1的配合物[环-CH 2 [CH 2 Sn（Cl 2）CH 2 Si（Me 2）]
• Altmann, Reiner; Gausset, Olivier; Horn, Dagmar, Organometallics, 2000, vol. 19, p. 430 - 443
  作者：Altmann, Reiner、Gausset, Olivier、Horn, Dagmar、Jurkschat, Klaus、Schuermann, Markus、et al.

  DOI：——

  日期：——
• Bis(halodiphenylstannyl)alkanes as Bidentate Lewis Acids toward Halide Ions
  作者：Dainis Dakternieks、Klaus Jurkschat、Hongjian Zhu、Edward R. T. Tiekink

  DOI：10.1021/om00005a057

  日期：1995.5

  Sn-119 and F-19 NMR spectroscopies were used to study reaction of bis(halodiphenylstannyl)alkanes (Ph(2)XSn)(2)(CH2)(n) (X = F, Cl, Br, I; n = 1, 2, 3) with various halide ions in dichloromethane solution. Ah three series of bis(halodiphenylstannyl)alkanes, (Ph(2)XSn)(2)-(CH2)(n) (X = F, Cl, Br, I; n = 1, 2, 3), exhibit chelate ability toward halide, forming anionic 1:1 adducts [(Ph(2)XSn)(2)(CH2)(n)X](-) which are static at -100 degrees C on the NMR time scale. The bis(halodiphenystannyl) alkanes always preferentially chelate fluoride ion over chloride or bromide. Endocyclic Sn-CH2 rotation brings about intramolecular exchange between bridging and terminal fluorine atoms at higher temperature. For n = 1, and 1:1 adducts [(Ph(2)XSn)(2)(CH2)X](-) react with additional fluoride (but not chloride or bromide) eventually to give [(Ph(2)F(2)Sn)(2)(CH2)(2)](2-) in which both tin atoms are five-coordinated. For n = 2, the 1:1 adducts [(Ph(2)XSn)(2)(CH2)(2)X](-) appear particularly stable and there is no evidence for formation of 1:2 adducts [(Ph(2)X(2)Sn)(2)(CH2)(2)](2-). Propylene-bridged 1:1 adducts, [(Ph(2)XSn)(2)(CH2)(3)X](-), react with both fluoride and chloride to give 1:2 adducts, [(Ph(2)F(2)Sn)(2)(CH2)(3)](2-) and [(Ph(2)Cl(2)Sn)(2)(CH2)(3)](2-), respectively, in which the tin atoms remain five-coordinated. The crystal structures of [(Ph(2)FSn)(2)CH2F](-) (1), [(Ph(2)BrSn)(2)CH2F](-) (4), [(Ph(2)ISn)(2)CH2F](-) (8), and [(Ph(2)ClSnCH(2))(2)F](-) (11), as their tetraethylammonium salts (la, 4a, 8a, and 11a, respectively), are described. Colorless crystals of la are monoclinic, space group P2(1)/n, with a = 11.695(4) Angstrom, b = 14.667(2) Angstrom, c = 18.956(2) Angstrom, beta = 103.33(1)degrees, V = 3164(1) Angstrom(3) and Z = 4. Colorless crystals of 4a are monoclinic, space group Cc with a = 11.758(1) Angstrom, b = 14.880(2) Angstrom, c = 19.316(2) Angstrom, beta = 93.981(9)degrees, V = 3371.3(6) Angstrom(3), and Z = 4. Colorless crystals of 8a are monoclinic, space group P2(1)/n, with a = 10.032(1) Angstrom, b = 16.993(3) Angstrom, c = 20.523(3) Angstrom, beta = 99.65(1)degrees, V = 3434.9(8) Angstrom(3), and Z = 4, Colorless crystals of 11a are monoclinic, space group P2(1), with a = 9.562(2) Angstrom, b = 15.529(4) Angstrom, c = 11.359(4) Angstrom, beta = 95.51(2)degrees, V = 1678.9(9) Angstrom(3), and Z = 2. The structures were refined to final R = 0.027, 0.029, 0.033, and 0.029 for 4661, 2647, 3843, and 3457 reflections with I greater than or equal to 3.0 sigma(I), respectively.
• Methylene-Bridged Tri- and Tetratin Compounds as Lewis Acids
  作者：Reiner Altmann、Klaus Jurkschat、Markus Schürmann、Dainis Dakternieks、Andrew Duthie

  DOI：10.1021/om970537u

  日期：1997.12.1

  crystal structure of [(Ph2FSnCH2)2SnFPh·F]-[C12H24O6·K]+ (6b) is described. Variable temperature 119Sn and 19F NMR studies indicate that the structure observed for the anion in 6b in the solid state is retained in solution. There is no NMR evidence for the formation of 1:2 adducts with fluoride ion, although such species are identified in acetonitrile solutions from electrospray mass spectrometry (ESMS)

  一系列三核锡化合物（Ph 2 XSnCH 2）2 SnXPh（2，X = Ph; 6，X = F; 8，X = Cl）和（PhCl 2 SnCH 2）2 SnCl 2（10）的合成报道了四核锡化合物（Ph 2 XSnCH 2 SnXPh）2 CH 2（3，X = Ph; 7，X = F; 9，X = Cl），[[（Ph 2 FSnCH 2）2 SnFPh· F] -描述了[C 12 H 24 O 6 ·K] +（6b）。可变温度119 Sn和19 F NMR研究表明，观察到的6b固态阴离子的结构保留在溶液中。尽管在电喷雾质谱（ESMS）的乙腈溶液中发现了这类物质，但没有NMR证据表明与氟离子形成1：2加合物。119 Sn NMR光谱数据表明三核锡化合物8与[（Ph 3 P）2 N] + Cl-的反应。HMPA形成1：1络合物[（Ph 2 ClSnCH 2）2 SnClPh·Cl] - [（Ph