10,11-dibromodibenzocycloheptene | 16186-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 10,11-dibromodibenzocycloheptene
• CAS: 16186-25-7
• 化学式: C₁₅H₁₀Br₂
• 分子量: 350.052
• InChiKey: JMJLVJBKFKTYDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  421.186±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.735±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  10,11-dibromodibenzocycloheptene 在 KOtBu 作用下， 以 四氢呋喃 、 二氯甲烷 、 二氯甲烷-D2 、 溶剂黄146 为溶剂， 生成 Pt(P(C₆H₅)3)2(Br)(C₁₅H₁₀)⁽¹⁺⁾*BF₄^(1-)=[Pt(P(C₆H₅)3)2(Br)(C₁₅H₁₀)]BF₄
  参考文献：
  名称：

  环炔烃和Tropynes铂配合物的合成和反应性

  摘要：

  Platinum complexes of dibenzannelated didehydrotropone 5, didehydrooxepin 6, and didehydrocycloheptatriene 7 have been synthesized in good yields by base-induced dehydrobromination from the corresponding bromoalkenes in the presence of Pt(PPh(3))(3). Complex 5 crystallizes in triclinic space group P1: a 11.221(2) Angstrom, b 11.318(2) Angstrom, c 16.621(4) Angstrom, alpha = 74.22(2)degrees, beta = 78.86(2)degrees, gamma = 73.56(2)degrees, V= 2445.0(9) Angstrom(3), Z = 2, R = 5.79%. Reaction of 5 with tert-butyl isocyanide gives a single phosphine displacement product 11, and reaction with HBF4 and HBr gives oxidative addition products 8 and 12, respectively. Bis(dicyclohexylphospkino)ethane displaces triphenylphosphine from 5 and 6 to give 9 and 10, Complex 5 reacts with tetracyanoethylene to give the highly distorted substituted benzene 14 which was characterized by X-ray diffraction. Crystal data for 14: Space group P1, a = 11.274(2) Angstrom, b = 11.826(1) Angstrom, c = 13.474(2) Angstrom, alpha 111.79(1)degrees, beta 106.34(1)degrees, gamma = 98.54(1)degrees, V = 1534.9(4) Angstrom(3), Z = 2, R 6.17%. Complex 6 reacts with TCNE, to give the platinacyclopent-2-ene 15 (55%). Complex 15 crystallizes in monoclinic space group la: a = 17.175(3) Angstrom, b = 15.411(2) Angstrom, c = 18.661(2) Angstrom, beta = 91.86(1)degrees, V= 4915(2) Angstrom(3), R = 4.74%. Reaction of 7 with triphenylcarbenium tetrafluoroborate gives the dibenzannelated tropyne complex 16 which can be converted back to 7 with KBEt(3)H. Reaction of 16 with bis(dicyclohexylphosphino)ethane gives 17 (60%), and reaction with HBr gives the oxidative addition product 18 which slowly isomerizes to 19.

  DOI：

  10.1021/om00006a039