1,2-bis(diphenylfluorostannyl)ethane | 164527-16-6

• 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: 1,2-bis(diphenylfluorostannyl)ethane
• 英文别名: (Ph2FSn)2(CH2)2
• CAS: 164527-16-6
• 化学式: C₂₆H₂₄F₂Sn₂
• 分子量: 611.893
• InChiKey: IDEXLSNYLQGNQY-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,2-bis(diphenylfluorostannyl)ethane 、 Tetraethylammonium fluoride dihydrate 以 二氯甲烷 为溶剂， 以99%的产率得到
  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
• 作为产物：
  描述：

  potassium fluoride 、 bis(triphenyltin)ethyl 在 I₂ 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 以76%的产率得到1,2-bis(diphenylfluorostannyl)ethane
  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 Molecular Organotin Oxides Derived from Alkylidene Bridged Ditin Precursors:  Syntheses and Structures^,
  作者：Bernhard Zobel、Markus Schürmann、Klaus Jurkschat、Dainis Dakternieks、Andrew Duthie

  DOI：10.1021/om980369l

  日期：1998.8.1

  New diorganotin compounds (RCl2Sn)(2)(CR'(2))(n) [R = (SiMe3)(2)CH; R' = Me, H; n = 1-3] Linked by various spacers have been synthesized. These react with sodium hydroxide or (t-Bu2SnO)(3) to give (R(O)Sn)(2)(CR'(2))(n). Compounds 8 (R' = Me, n = 1), 9 (R' = H, n = 2), and 10 (R' = H, n = 3) contain four-coordinate tin atoms. Compound 9 undergoes a reversible hydrolysis reaction from which a solid containing three ditin units has been isolated. Evidence is presented for the existence in solution of monomeric four-coordinate tin compounds (RXSn)(2)(CH2)(3)O [R = (SiMe3)(2)CH, X = Cl, OH]. Crystal structures for monomeric ditin precursors 2,2-bis[bis(trimethylsilyl)methyldichlorostannyl]propane (3) and 1,2-bis[bis(trimethylsilyl)methyldichlorostannyl]ethane (6), for dimeric units 1,3,5,7-tetrakis[bis(trimethylsilyl)methyl]-9,9,10,10-tetramethyl-2,4,6,8-tetraoxa-1,3,5,7-tetrastannaadamantane (8), 1,3,7,9-tetrakis[bis(trimethylsilyl)methyl]-2,8,13,14-tetraoxatricyclo[7.3.1.13.7]-1,3,7,9-tetrastannatetradecane (10), and 2,6-difluoro-2,6-bis[bis(trimethylsilyl)methyl]-1-oxa-2,6-distannacyclohexane dimer (12), and for trimeric units O[(RSn(CH2)(2)SnR)OH]OH}(3). 2H(2)O (9a) are reported.