4-phenyl-1,1,3,3-tetrachloro-1,3-disilacyclopentane | 653603-28-2

• 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: 4-phenyl-1,1,3,3-tetrachloro-1,3-disilacyclopentane
• 英文别名: 1,1,3,3-Tetrachloro-4-phenyl-1,3-disilolane；1,1,3,3-tetrachloro-4-phenyl-1,3-disilolane
• CAS: 653603-28-2
• 化学式: C₉H₁₀Cl₄Si₂
• 分子量: 316.161
• InChiKey: AGYBPMJQLDBANY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  bis(dichlorosilyl)methane 、 苯乙炔 在 Speier's catalyst 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以33%的产率得到4-phenyl-1,1,3,3-tetrachloro-1,3-disilacyclopentane
  参考文献：
  名称：

  Platinum-catalyzed double silylations of alkynes with bis(dichlorosilyl)methanes

  摘要：

  Bis(dichlorosilyl)methanes 1 undergo the two kind reactions of a double hydrosilylation and a dehydrogenative double silylation with alkynes 2 such as acetylene and activated phenyl-substituted acetylenes in the presence of Speier's catalyst to give 1,1,3,3-tetrachloro-1,3-disilacyclopentanes 3 and 1,1,3,3-tetrachloro-1,3-disilacyclopent-4-enes 4 as cyclic products, respectively, depending upon the molecular structures of both bis(dichlorosilyl)methanes (1) and alkynes (2). Simple bis(dichlorosilyl)methane (1a) reacted with alkynes [R-1-C C-R-2: R-1 = H, R-2 = H (2a), Ph (2b); R-1 = R-2 = Ph (2c)] at 80 degrees C to afford 1,1,3,3-tetrachloro-1,3-disilacyclopentanes 3 as the double hydrosilylation products in fair to good yields (33-84%). Among these reactions, the reaction with 2c gave a trans-4,5-diphenyl1,1,3,3-tetrachloro-1,3-disilacyclopentane 3ac in the highest yield (84%). When a variety of bis(dichlorosilyl)(silyl)methanes [(Me-n-Cl-3- Si-n)CH(SiHCl2)(2): n = 0 (1b), 1 (1c), 2 (1d), 3 (1e)] were applied in the reaction with alkyne (2c) under the same reaction conditions. The double hydrosilylation products, 2-silyt-1,1,3,3-tetrachloro-1,3-disilacyclopentanes (3), were obtained in fair to excellent yields (38-98%). The yields of compound 3 deceased as follows: n = 1 > 2 > 3 > 0. The reaction of alkynes (2a-c) with 1c under the same conditions gave one of two type products of 1,1,3,3-tetrachloro-1,3-disilacyclopentanes 3 and 1,1,3,3-tetrachloro-1,3-disilacyclopent-4-enes (4): simple alkyne 2a and terminal 2b gave the latter products 4ca and 4cb in 91% and 57% yields, respectively, while internal alkyne 2c afforded the former cyclic products 3cc with trans form between two phenyl groups at the 3- and 4-carbon atoms in 98% yield, respectively. Among platinum compounds such as Speier's catalyst, PtCl2(PEt3)(2), Pt(PPh3)(2)(C2H4), Pt(PPh3)(4), Pt[ViMeSiO](4), and Pt/C, Speier's catalyst was the best catalyst for such silylation reactions. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.10.001

文献信息

• Platinum-catalyzed double silylations of alkynes with bis(dichlorosilyl)methanes
  作者：Son Thanh Phan、Weon Cheol Lim、Joon Soo Han、Il Nam Jung、Bok Ryul Yoo

  DOI：10.1016/j.jorganchem.2005.10.001

  日期：2006.2

  Bis(dichlorosilyl)methanes 1 undergo the two kind reactions of a double hydrosilylation and a dehydrogenative double silylation with alkynes 2 such as acetylene and activated phenyl-substituted acetylenes in the presence of Speier's catalyst to give 1,1,3,3-tetrachloro-1,3-disilacyclopentanes 3 and 1,1,3,3-tetrachloro-1,3-disilacyclopent-4-enes 4 as cyclic products, respectively, depending upon the molecular structures of both bis(dichlorosilyl)methanes (1) and alkynes (2). Simple bis(dichlorosilyl)methane (1a) reacted with alkynes [R-1-C C-R-2: R-1 = H, R-2 = H (2a), Ph (2b); R-1 = R-2 = Ph (2c)] at 80 degrees C to afford 1,1,3,3-tetrachloro-1,3-disilacyclopentanes 3 as the double hydrosilylation products in fair to good yields (33-84%). Among these reactions, the reaction with 2c gave a trans-4,5-diphenyl1,1,3,3-tetrachloro-1,3-disilacyclopentane 3ac in the highest yield (84%). When a variety of bis(dichlorosilyl)(silyl)methanes [(Me-n-Cl-3- Si-n)CH(SiHCl2)(2): n = 0 (1b), 1 (1c), 2 (1d), 3 (1e)] were applied in the reaction with alkyne (2c) under the same reaction conditions. The double hydrosilylation products, 2-silyt-1,1,3,3-tetrachloro-1,3-disilacyclopentanes (3), were obtained in fair to excellent yields (38-98%). The yields of compound 3 deceased as follows: n = 1 > 2 > 3 > 0. The reaction of alkynes (2a-c) with 1c under the same conditions gave one of two type products of 1,1,3,3-tetrachloro-1,3-disilacyclopentanes 3 and 1,1,3,3-tetrachloro-1,3-disilacyclopent-4-enes (4): simple alkyne 2a and terminal 2b gave the latter products 4ca and 4cb in 91% and 57% yields, respectively, while internal alkyne 2c afforded the former cyclic products 3cc with trans form between two phenyl groups at the 3- and 4-carbon atoms in 98% yield, respectively. Among platinum compounds such as Speier's catalyst, PtCl2(PEt3)(2), Pt(PPh3)(2)(C2H4), Pt(PPh3)(4), Pt[ViMeSiO](4), and Pt/C, Speier's catalyst was the best catalyst for such silylation reactions. (c) 2005 Elsevier B.V. All rights reserved.