2-(tributylstannyl)norbornadiene | 107195-08-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 2-(tributylstannyl)norbornadiene
• CAS: 107195-08-4
• 化学式: C₁₉H₃₄Sn
• 分子量: 381.189
• InChiKey: WXZNCBAMWVJUIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  三甲基氯硅烷 、 2-(tributylstannyl)norbornadiene 在 正丁基锂 作用下， 生成 2-(trimethylsilyl)bicyclo<2.2.1>hepta-2,5-diene
  参考文献：
  名称：

  Polymers containing ring-strain energy. 1. New monomers and polymers based on cyclopropane, norbornadiene, and quadricyclane

  摘要：

  The synthesis and polymerization chemistry of 1,1-bis(XCH2)cyclopropane {1, X = OH; 4, X = I} was studied. Treatment of 1 with base in the presence of alpha,omega-dihalides did not produce a polyether. However, treatment of 4 with the bis(alkoxide) derived from hexanediol afforded a polyether of low molecular weight {M(n) = 3000, PD = 3}. A general method for alkylating norbornadiene in the 2-position was developed. Treatment of norbornadiene with tert-BuOK, tetramethylethylenediamine (TMEDA), n-BuLi, and tributylchloroetannane (in that order) afforded 2-(tributylstannyl)norbornadiene in excellent yield. On the other hand, carbon electrophiles {eg. bromobutane, 1,4-dibromobutane, and 2,3-dichloropropene} required the generation of the 2-(lithiocyanocuprate) in order to effect clean alkylation. Treatment of 2-[3-(2-chloropropenyl)]norbornadiene (8a) with RMgX {where R = vinyl and phenyl} in the presence of (dppp)NiCl2 afforded the cross-coupling products 2-(XCH2)-norbornadiene {9, X = 2-buta-1,3-dienyl; 10, X = alpha-styryl; respectively} in high yield. Polymerization of 9 in THF initiated by n-BuLi resulted in an elastomeric polymer (12) [M(n) = 18,000, PD = 1.5]. Photolysis of 12 in the presence of (Ph3P)2CuBr converted the pendant norbornadiene to quadricyclane (13). Heating of the photoisomerized sample to 180-degrees-C caused an exothermic (by DSC) reaction which corresponded to 59% of theory (using the value 26 kcal/mol: quadricyclane --> norbornadiene).

  DOI：

  10.1021/jo00067a055
• 作为产物：
  描述：

  tributyl-[3-(4-methylphenyl)sulfonyl-2-bicyclo[2.2.1]hepta-2,5-dienyl]stannane 以56%的产率得到
  参考文献：
  名称：

  DJEGHABA, Z.;JOUSSEAUME, B.;RATIER, M.;DUBOUDIN, J. -G., J. ORGANOMET. CHEM., 1986, 304, N 1-2, 115-125

  摘要：

  DOI：

文献信息

• Sulfones organostanniques: synthese et reactivite des trialkystannyl-1 para-toluenesulfonyl-2 acetylenes
  作者：Zeineddine Djeghaba、Bernard Jousseaume、Max Ratier、Jean-Georges Duboudin

  DOI：10.1016/s0022-328x(00)99680-3

  日期：1986.4
• Hydrostannation of norbornadiene by nBu3SnH and Ph3SnH with molybdenum catalysts
  作者：Magdalena Zyder、Teresa Szymańska-Buzar

  DOI：10.1016/j.jorganchem.2010.03.023

  日期：2010.6

  Photochemicallyactivated [Mo(CO)(6)] and [Mo(CO)(4)(eta(4)-nbd)] are demonstrated to be good catalysts for the hydrostannation of norbornadiene (nbd) by stannyl hydrides ((Bu3SnH)-Bu-n and Ph3SnH) to give stannylnorbornene in ca. 100% yield. The reaction was carried out at room temperature in n-heptane (20 cm(3)) with continued photolysis (2h) at Mo(CO)(6): R3SnH:nbd = 1:50:50. (C) 2010 Elsevier B.V. All rights reserved.
• Polymers containing ring-strain energy. 1. New monomers and polymers based on cyclopropane, norbornadiene, and quadricyclane
  作者：Michael E. Wright、Gary D. Allred、Robert B. Wardle、Louis F. Cannizzo

  DOI：10.1021/jo00067a055

  日期：1993.7

  The synthesis and polymerization chemistry of 1,1-bis(XCH2)cyclopropane 1, X = OH; 4, X = I} was studied. Treatment of 1 with base in the presence of alpha,omega-dihalides did not produce a polyether. However, treatment of 4 with the bis(alkoxide) derived from hexanediol afforded a polyether of low molecular weight M(n) = 3000, PD = 3}. A general method for alkylating norbornadiene in the 2-position was developed. Treatment of norbornadiene with tert-BuOK, tetramethylethylenediamine (TMEDA), n-BuLi, and tributylchloroetannane (in that order) afforded 2-(tributylstannyl)norbornadiene in excellent yield. On the other hand, carbon electrophiles eg. bromobutane, 1,4-dibromobutane, and 2,3-dichloropropene} required the generation of the 2-(lithiocyanocuprate) in order to effect clean alkylation. Treatment of 2-[3-(2-chloropropenyl)]norbornadiene (8a) with RMgX where R = vinyl and phenyl} in the presence of (dppp)NiCl2 afforded the cross-coupling products 2-(XCH2)-norbornadiene 9, X = 2-buta-1,3-dienyl; 10, X = alpha-styryl; respectively} in high yield. Polymerization of 9 in THF initiated by n-BuLi resulted in an elastomeric polymer (12) [M(n) = 18,000, PD = 1.5]. Photolysis of 12 in the presence of (Ph3P)2CuBr converted the pendant norbornadiene to quadricyclane (13). Heating of the photoisomerized sample to 180-degrees-C caused an exothermic (by DSC) reaction which corresponded to 59% of theory (using the value 26 kcal/mol: quadricyclane --> norbornadiene).
• DJEGHABA, Z.;JOUSSEAUME, B.;RATIER, M.;DUBOUDIN, J. -G., J. ORGANOMET. CHEM., 1986, 304, N 1-2, 115-125
  作者：DJEGHABA, Z.、JOUSSEAUME, B.、RATIER, M.、DUBOUDIN, J. -G.

  DOI：——

  日期：——