Ph3SnC*CC*CSnPh3 | 1262-93-7

• 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: Ph3SnC*CC*CSnPh3
• 英文别名: 1,4-bis(triphenylstannyl)-1,3-butadiyne
• CAS: 1262-93-7
• 化学式: C₄₀H₃₀Sn₂
• 分子量: 748.098
• InChiKey: HNKDIQKKBXVBJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  Ph3SnC*CC*CSnPh3 、 2-氯丙烷 以 further solvent(s) 为溶剂， 生成 (Ph3SnC*CC*CSnPh3)*isopropyl chloride
  参考文献：
  名称：

  Inclusion Properties of 1,4-(Triorganostannyl and -silyl)buta-1,3-diynes:  Thermal, Structural, and NMR Spectroscopic Aspects

  摘要：

  The tin-containing diyne Ph3SnC equivalent to CC equivalent to CSnPh3 (4) forms 1:1 host-guest complexes with a large variety of organic molecules. These complexes have been characterized by H-1 NMR spectroscopy, thermogravimetry (TGA), and differential scanning calorimetry (DSC). Weak interactions between the host and guest molecules are observed with toluene, tetrachloroethane, and p-xylene (the latter gives a 2:1 complex). Strong interactions are found with dichloromethane, chloroform, tetrahydrofuran, and dioxane. An intermediate behavior is observed with acetone, benzene, and pyridine. Guest-selectivity studies have been carried out on some of these complexes that confirm the results obtained from the TGA measurements. A single-crystal X-ray diffraction analysis of 4:dioxane shows that it has a true clathrate (cage) structure with the guest molecule being surrounded by 12 phenyl groups from 6 Ph3Sn moieties. Inclusion compounds do not form when the length of the spacer is shortened, i.e. with Ph3SnC equivalent to CSnPh3, or when the SnPh3 groups of 4 are replaced by SnMe3 moieties. On going from Ph3SnC equivalent to CC equivalent to CSnPh3 to Ph3Sn(CH2)(4)SnPh3, i.e. when the rigid diacetylene fragment is replaced by the flexible butanediyl group, formation of a clathrate is observed only in the case of dioxane. When Ph2PC equivalent to CC equivalent to CPPh2 or Ph3SiC equivalent to CC equivalent to CSiPh3 is used as host instead of Ph3SnC equivalent to CC equivalent to CSnPh3, there is no evidence for clathrate formation. However, in the case of Ph3SiC equivalent to CC equivalent to CSi*MePhNp (5: Np = 1-naphthyl), a 1:1 clathrate is obtained with dioxane. A single-crystal X-ray diffraction analysis of the 5:dioxane inclusion compound shows that the guest molecule lies exclusively in channels formed by phenyl substituents from the Ph3Si groups. Solid-state C-13, Sn-119, and Si-29 NMR and X-ray powder diffraction analyses have been carried out on 4:CHCl3, 4:dioxane and 5:dioxane prior to and after removal of the guest molecules, and the results demonstrate the structure-stabilizing ability of these molecules. It has been possible to obtain single crystals of 4 with no included solvent, and the X-ray crystal structure of this material shows that the organization of the diacetylenic compound is such that it leads to a more compact packing as compared to that found in 4:dioxane.

  DOI：

  10.1021/om9804430
• 作为产物：
  描述：

  1,4-dilithio-1,3-butadiyne 、 三苯基氯化锡 以 四氢呋喃 为溶剂， 以78%的产率得到Ph3SnC*CC*CSnPh3
  参考文献：
  名称：

  新型聚[（亚甲硅基）二乙炔]和聚[（亚甲二基）二乙炔]：合成与导电性能

  摘要：

  The reaction of dilithiobutadiyne (or the corresponding di-Grignard reagent) with various dichlorosilanes and dibromogermanes in THF at room temperature afforded poly[(silylene)diacetylenes] and poly[(germylene)diacetylenes], respectively, in high yields. The polymers have a regular alternating arrangement of diyne and silylene or germylene units. When they are doped with FeCl3, these polymers show conductivity values in the range 10(-5)-10(-3) S.cm-1. The values depend greatly on the electronic character of the substituents bonded to silicon or germanium.

  DOI：

  10.1021/om00043a037

文献信息

• Synthesis and reactivity of dinuclear rhodium complexes with RhCCHR and RhCCCRR′ units as building blocks
  作者：Berta Callejas-Gaspar、Matthias Laubender、Helmut Werner

  DOI：10.1016/s0022-328x(03)00521-7

  日期：2003.11

  The reaction of [Rhκ2-O2S(O)CF3}(PiPr3)2] (1) with ethynylferrocene in the presence of KF affords the substituted vinylidene complex trans-[RhFCCH(C5H4)Fe(C5H5)}(PiPr3)2] (2) which upon treatment with the butadiyne derivative Ph3SnCCCCSnPh3 produces the chain-like compound trans-[(μ-CCCC)Rh(CCH(C5H4)Fe(C5H5))(PiPr3)2}2] (7). The triflato complex 1 reacts with 1,4-C6H4(CCH)2 to give the

  的的[Rh κ反应2 -O 2 S（O）CF 3 }（P我镨3）2 ]（1），在KF存在ethynylferrocene，得到取代的亚乙烯基复杂的反式[RHF CCH - （C 5 H ^ 4）的Fe（C 5 H ^ 5）}（P我镨3）2 ]（2），其在与所述丁二炔衍生物pH处理3 SnCCCCSnPh 3产生链状化合物反式- [（μ-CCCC）Rh（CCH（C 5 H 4）Fe（C 5 H 5））（P i Pr 3）2 } 2 ]（7）。三氟甲磺酸盐络合物1与1,4-C 6 H 4（CCH）2反应，生成双核化合物反式-[μ-1,4- C6 H 4（CHC）2 } Rh（ η 1 -OS（O）2 CF 3）（P我镨3）2 } 2 ]（3），在存在KF的情况下进行配体交换，得到相应的二氟衍生物4。由4和RC ＝CSnPh 3（R ＝ CH 3，C 6 H 5）得到配合物5和6，其中C
• Synthesis of Dinuclear Rhodium Complexes with 1,3-Butadiyndiyl Bridges. Coupling of the C₄ and the Two C₂ Units of a C₂RhC₄RhC₂ Chain^,¹
  作者：Juan Gil-Rubio、Matthias Laubender、Helmut Werner

  DOI：10.1021/om990960y

  日期：2000.4.1

  derivatives trans,trans-[Rh(CX)(PiPr3)2}2(μ-C⋮C−C⋮C)] (12, 13) were obtained. The reactions of 8 and 9 with equimolar amounts of Ph3SnC⋮C−C⋮CSnPh3 gave the mononuclear complexes trans-[Rh(C⋮C−C⋮CSnPh3)(CX)(PiPr3)2] (10, 11), which on further treatment with 8 or 9 afforded the dinuclear compounds 12 and 13, respectively. The C−SnPh3 bond of 10 could be cleaved both by Al2O3/H2O and trans-[RhF(CCHPh)(PiPr3)2]

  化合物的反式- [RHF（Ç CHR）（P我镨3）2 ]（2 - 4），其中2（R = H）的第一次从铑[Rh制备η 2 -O 2 S（O） CF 3 }（P i Pr 3）2 ]，C 2 H 2和KF与Ph 3 SnC⋮C-C⋮CSnPh 3反应，得到双核C 4桥连铑（I）配合物，反式，反式-[ Rh（C CHR）（P iPR 3）2 } 2（μ-C⋮C-C⋮C）]（5 - 7）在78-88％的分离收率。在类似的路线上，通过使用反式-[RhF（CX）（P i Pr 3）2 ]（8，CX = CNC 6 H 3 Me 2 -2,6; 9，CX = CO）和Ph 3 SnC⋮C以摩尔比为2：1的-C 2：CSnPh 3为原料，二异氰基二ho基和二羰基二derivatives基衍生物trans，trans -[Rh（CX）（P i Pr 3）2} 2（μ-C⋮C-C⋮C）]（12，13）获得。的反应8和9与等摩尔量的Ph
• Venkatesan, Koushik; Fernandez, Francisco J.; Blacque, Olivier, Chemical Communications
  作者：Venkatesan, Koushik、Fernandez, Francisco J.、Blacque, Olivier、Fox, Thomas、Alfonso, Montserrat、et al.

  DOI：——

  日期：——
• Synthetic Access to Half-Sandwich Manganese C₄ Cumulenic Complexes
  作者：Koushik Venkatesan、Olivier Blacque、Thomas Fox、Montserrat Alfonso、Helmut W. Schmalle、Heinz Berke

  DOI：10.1021/om049551e

  日期：2004.9.1

  The vinylalkynyl complexes Mn(C5H4R')(R"2PCH2CH2PR"(2))(=C CSnPh3C=-CSnPh3) (5, 6) were obtained in good yields by treatment of Mn(C5H4R')(eta(6)-cycloheptatriene) (R' = H (1a), Me (1b)) with 1 equiv of Ph(3)SnCdropCCdropCSnPh(3) and R"2PCH2CH2PR"(2) (R" = CH3 (dmpe), C2H5 (depe)). The theoretically characterized (DFT) C-4 cumulenic species Mn(C5H4R')(R"2PCH2CH2PR"(2))=C=C=C C(SnPh3)(2)} (7, 8) were obtained by photolysis of the tin-substituted vinylalkynyl complexes 5 and 6. Subsequently 7 and 8 could be converted into the parent cumulenic species Mn(C5H4R')(R"2PCH2CH2PR"(2))=C=C=C=C(H)(2)} (9, 10) by reacting complexes 7 and 8 with TBAF (5% H2O) at -40 degreesC. The difference in the thermodynamic stabilities between the complexes 7 and 8 and complexes 9 and 10 was traced by DFT calculations using Mn(C5H5)(dHpe)=C=C=C=C(SnMe3)(2)} (4-H) and Mn(C5H5)(dHpe)=C=C=C=CH2} (9-H) as model complexes. Treatment of the vinylalkynyl complex with an excess of MeOH led to the formation of a dinuclear complex with a C-8 chain between two manganese centers. The cumulenic complexes and the vinylalkynyl complexes were characterized by NMR and vibrational spectroscopy and elemental analyses. An X-ray diffraction study has been performed on complex 4b.
• Dinuclear Rhodium Complexes Containing a Linear C₂RhC₄RhC₂ Chain¹
  作者：Juan Gil-Rubio、Matthias Laubender、Helmut Werner

  DOI：10.1021/om9710780

  日期：1998.3.1

  The reaction of trans-[RhCl(=C=CHPh)(PiPr(3))(2)] (1) and trans-[RhCl(=C=CMe2)(PiPr(3))(2)] (3) with 50% aqueous NaOH, in the presence of TEBA, afforded the hydroxorhodium complexes trans-[Rh(OH)(=C=CRR')(PiPr(3))(2)] (2,4) in good to excellent yield. Compound 2 (R = H, R' = Ph) reacted with D2O to give trans-[Rh(OD)(=C=CHPh)(PiPr(3))(2)] (2-d) and with Bronsted acids HX (X = CF3CO2, OPh, C=Ph) to yield the corresponding derivatives trans-[Rh(X)(=C=CHPh)(PiPr(3))(2)] (5-7), respectively. Treatment of 2 and 4 with Ph-3-SnC=CC=CSnPh3 also led to the displacement of the hydroxo ligand and to the formation of the dinuclear complexes trans,trans-[(Rh(=C-CRR')(PiPr(3))(2)](2)(mu-C-4)] (8,9) in 75-80% yield. The X-ray crystal structure analysis of 9 revealed the presence of a linear l0-atom C=C=RhC=CC=CRh=C=C chain with the midpoint of the central C-C bond as a crystallographic center of symmetry.