tetrabromodiazocyclopentadiene | 38123-55-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 英文名称: tetrabromodiazocyclopentadiene
• 英文别名: 1,2,3,4-Tetrabromo-5-diazocyclopenta-1,3-diene
• CAS: 38123-55-6
• 化学式: C₅Br₄N₂
• 分子量: 407.684
• InChiKey: GHWZZRGFHOVMCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tetrabromodiazocyclopentadiene 在 氧气 作用下， 生成 tetrabromocyclopentadienone
  参考文献：
  名称：

  A spectroscopic study of the reaction of the carbene, tetrabromocyclopentadienylidene, with O2 in low temperature matrices

  摘要：

  The photolysis of tetrabromodiazocyclopentadiene (2) in low temperature Ar and N2 matrices generates the carbene, tetrabromocyclopentadienylidene (3). In O2-doped matrices, (3) reacts with oxygen yielding first tetrabromocyclopentadienone O-oxide (4), identification of which was aided by experiments with isotopically labelled oxygen, and then tetrabromocyclopentadienone (5) and tetrabromo-alpha-pyrone (6). The matrix uv-visible and infrared absorption spectra of tetrabromocyclopentadienone O-oxide (4) are reported.

  DOI：

  10.1016/0584-8539(94)80123-1
• 作为产物：
  描述：

  hexabromocyclopenta-1,3-diene 在 lead(IV) acetate 、 magnesium sulfate 、 肼 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 生成 tetrabromodiazocyclopentadiene
  参考文献：
  名称：

  Preparation and photolytic decomposition of tetrabromodiazocyclopentadiene 3

  摘要：

  DOI：

  10.1021/jo00947a019

文献信息

• Übergangsmetall-methylen-komplexe
  作者：Wolfgang A. Herrmann、Martina Flöel、Cornelia Weber、John L. Hubbard、Adolf Schäfer

  DOI：10.1016/0022-328x(85)80052-8

  日期：1985.5

  The eighteen new μ-alkylidene ruthenium complexes 5a–r and 5t are very easily and cleanly obtained along the diazoalkane or the hydrazone routes that involve treatment of the dinuclear, metal-metal doubly bonded precursor compound [(η5-C5H5)Ru(μ-NO)]2 (3) either with the diazoalkanes oxidizing agent (e.g., MnO2), with the respective hydrazones. Similarly, sulfur dioxide adds cleanly to the RuRu double

  十八新μ亚烷基钌配合图5a-R和5吨非常容易且干净地沿着重氮烷或涉及治疗双核，金属-金属双键前体化合物的腙途径获得[（η 5 -C 5 H ^ 5） Ru（μ-NO）] 2（3）或重氮烷烃氧化剂（例如MnO 2）和相应的。类似地，二氧化硫干净地增加的RURU双键3，由此得到配合物（μ-SO 2）[（η 5 -C 5 H ^ 5）的Ru（NO）] 2（5S）。不管卡宾桥配体的性质如何，与它们的铁类似物相比，双金属环丙烷仅表现出末端亚硝酰基配体。对于显示出不对称取代的卡宾桥的衍生物，观察到具有占主导地位的反式异构体的顺式/反式异构现象。
• Convenient syntheses of “heavy fluorous” cyclopentadienes and cyclopentadienyl complexes with three to five ponytails
  作者：Long V. Dinh、J. A. Gladysz

  DOI：10.1039/b401540a

  日期：——

  4, 5) and IZn(CH2)2R(f8) in the presence of Cl2PdL2 catalysts give the title complexes (eta5)-C5H(5-x)(CH2)2R(f8)x)M(CO3), accompanied in the case of x= 5 by hydride-transfer byproducts. Extremely high fluorophilicities are realized, and the cyclopentadienyl ligands are readily detached (hnu) from the manganese complexes.

  （eta5-C5H（5-x）Brx）M（CO）3（M = Re，Mn; x = 1，3，4，5）和IZn（CH2）2R（f8）在Cl2Pdref=https://www.molaid.com/MS_3163 target="_blank">L2 L2催化剂存在下的反应给出标题配合物（eta5）- （5-x）（ ）2R（f8）x）M（CO3），在x = 5的情况下伴随有氢化物转移副产物。实现了极高的亲氟性，并且环戊二烯基配体易于从锰配合物中脱离（hnu）。
• Coordination chemistry of perhalogenated cyclopentadienes XXII. Reaction of tetrabromodiazocyclopentadiene with some halide bridged Rh(I), Ru(II) and Ru(III) complexes. Molecular structure of [C5Br5]Rh(COD), a complex with an η1,η4-coordinated cyclopentadienyl ligand
  作者：Karlheinz Sünkel、Cornelia Stramm、Markus Lang、Werner Kempinger、Julian Hofmann

  DOI：10.1016/s0020-1693(97)05882-9

  日期：1998.3

  The halide bridged complexes [Cp*RuBr2](n) and [(COD)Rh(mu-X)](2) (X = Cl, Br) react with tetrabromodiazocyclopentadiene C5Br4N2 to give the pentahalocyclopentadienyl complexes Cp*Ru[C5Br5] (1a) and either [C5Br4Cl]Rh(COD) (2a) or [C5Br5]Rh(COD) (2b), respectively. Treatment of C5Cl4N2 with [Cp*RuBr](4) or [(COD)Rh(mu-Br)](2) yields the analogous complexes LnM [C5Cl4Br] (LnM = Cp*Ru (1b), (COD)Rh (2c)) in high yield. A crystal structure determination of 2b shows the cyclopentadienyl ligand in an unusual eta(1),eta(4)-bonding fashion. Crystals of 2b are orthorhombic, space group Pnma, a = 10.86(2), b = 12.841(5), c = 11.972(4) Angstrom, V = 1670(3) Angstrom(3), Z = 4, R1 = 5.81%, wR2 = 14.22%. (C) 1998 Elsevier Science S.A.
• Syntheses and structures of missing links among polybromocyclopentadienyl rhenium and manganese tricarbonyl complexes
  作者：Long V. Dinh、Frank Hampel、J.A. Gladysz

  DOI：10.1016/j.jorganchem.2004.09.072

  日期：2005.1

  Reactions of diazocyclopentacliene and NBS at appropriate stoichiometries give 2,5-dibromodiazocyclopentadiene and 2,3,5-tribromodiazocyclopentadiene in 40% and 30% yields, respectively, after chromatography. These react with BrRe(CO)(5) or BrMn(CO)(5) (80degreesC, CF3C6H5) to give (eta(5)-1 2,3-C5HBr3)M(CO)(3) (3; M = a, Re; b, Mn) and (eta(5) -C5HBr4)M(CO)(3) (4a,b) in 75-85% yields. In the case of 4a, the intermediate ill-cyclopentadienyl complex (eta(1)-C5HBr4)Re(CO)(5) (4'a) can be isolated (44%). An isomer of 3b, (eta(5)- 1,2,4-C5H2Br3)Mn(CO)(3), is accessed by desilylating previously reported (eta(5)-1,2,4-C-5(SiMe3)(2)Br-3)Mn(CO)(3) with CsF/MeOH (85%). The reaction of tetrabromodiazocyclopentadiene and BrRe(CO)(5) at 80degreesC in CF3C6H5 gives the eta(1)-cyclopentadienyl complex (eta(1) -C5Br5)Re(CO)(5) (5'a, 74%) which cannot be induced to decarbonylate to (eta(5) -C5Br5)Re(CO)(3) (5a) under a variety of conditions. However, 5a can be isolated (45%) when a similar reaction is conducted at 120degreesC. The IR properties of the preceding complexes are compared, and the crystal structures of 3a, 3b, 5a, and 5'a are determined and analyzed. (C) 2004 Elsevier B.V. All rights reserved.
• Herrmann, Wolfgang A.; Bauer, Christine; Kriechbaum, Gangolf, Chemische Berichte, 1982, vol. 115, # 3, p. 878 - 900
  作者：Herrmann, Wolfgang A.、Bauer, Christine、Kriechbaum, Gangolf、Kunkely, Horst、Ziegler, Manfred L.、at al.

  DOI：——

  日期：——