d1-vinyl chloride | 4984-12-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: d1-vinyl chloride
• 英文别名: α-d(1)-Vinylchlorid；Vinylchlorid-α-d1；Vinylchlorid-1-D；Deuterovinylchlorid；1-Chlor-1-deuterio-ethylen；1-Chlor-1-deutero-aethylen；1-chloro-1-deuterio-ethene；1-Chlor-1-deuterio-aethen；vinyl chloride；1-Chlor-1-deuterio-aethylen；1-Chloro-1-deuterioethene
• CAS: 4984-12-7
• 化学式: C₂H₃Cl
• 分子量: 63.4909
• InChiKey: BZHJMEDXRYGGRV-VMNATFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  3
• 可旋转键数：
  0
• 环数：
  0.0
• 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：

  d1-vinyl chloride 生成 氘乙炔 、 vinylidene biradical
  参考文献：
  名称：

  The ultraviolet photodissociation dynamics of d₁‐vinyl chloride

  摘要：

  We have used partially deuterated vinyl chloride to elucidate the photodissociation mechanism of this molecule. We have found that 75% of the HCl fragments are produced by three-center α,α elimination. Surprisingly, the rotational energy distributions of HCl are the same for both elimination pathways. One possible explanation is that H atom migration in the parent molecule results in similar transition states for the two pathways. Alternatively, dissociation and fragment isomerization may be strongly coupled so that the product angular momentum distribution is determined late in the reaction coordinate. Very different rotational state distributions were observed for v″=0 and v″≳0. We speculate that this dichotomy is caused by formation of a hydrogen-bonded π complex between HCl(v″≳0) and acetylene. We have also determined that HCl+ ions are produced primarily by an α,β mechanism. This mechanism consists of electronic excitation of vinyl chloride, followed by photoelimination and photoionization of electronically excited HCl*. Finally, we determined that H atoms are preferentially produced by detachment from the β carbon, as predicted from the relative stabilities of the α- and β-chlorovinyl radicals.  

  DOI：

  10.1063/1.465183
• 作为产物：
  描述：

  1,1-二氯乙烯 在 溴化氘 、 锌 作用下， 生成 d1-vinyl chloride
  参考文献：
  名称：

  Mechanism of the Reaction of Vinyl Chloride with (α-diimine)PdMe⁺ Species

  摘要：

  The reaction of vinyl chloride (VC) with (alpha-diimine)PdMe+ species yields (alpha-diimine)PdCl-(propene)(+) Isotope labeling experiments using the deuterium-labeled vinyl chlorides 1-VC-d(1) and Z-VC-d(1) combined with DFT computations establish that this reaction proceeds by 2,1-insertion of VC to produce beta-H agostic (alpha-diimine)Pd(CHClCH2Me)(+), chain-walking isomerization to generate beta-Cl dative (alpha-diimine)Pd(CHMeCH2Cl)(+) and syn beta-Cl elimination. The labeling experiments rule out mechanisms involving initial 1,2-insertion or C-Cl oxidative addition. The computational results and the observation of small amounts of propene-d(2) argue against mechanisms involving 2,1-insertion followed by alpha-Cl elimination and a 1,2 H-shift.

  DOI：

  10.1021/om1000925

文献信息

• Metal Ions Do Not Play a Direct Role in the Formation of Carbon-Carbon Triple Bonds during Reduction of Trihaloalkyls by Cr^IIor V^II
  作者：Ophir Levy、Avi Bino

  DOI：10.1002/chem.201202918

  日期：2012.12.7

  aqueous solutions yield alkynes and other products. Stepwise halogen abstractions from the trihaloalkyls form alkyl carbyne triradicals in solution. These radicals undergo coupling reactions, producing triply bonded alkyne molecules (see scheme). This process is not metal‐assisted and does not occur in the coordination sphere of the metal ions.

  卡宾基：水溶液中三卤代烷基化合物与Cr 2+或V 2+的反应生成炔烃和其他产物。从三卤代烷基逐步提取卤素在溶液中形成烷基卡宾三基。这些自由基进行偶联反应，生成三键结合的炔烃分子（请参见方案）。此过程不是金属辅助的，不会在金属离子的配位范围内发生。
• ORGANIC DEUTERIUM COMPOUNDS: XVIII. ADDITION PRODUCTS OF HYDROGEN AND DEUTERIUM BROMIDES TO 1,1-DICHLOROETHYLENE
  作者：J. E. Francis、L. C. Leitch

  DOI：10.1139/v57-070

  日期：1957.5.1

  The addition of hydrogen bromide to 1,1-dichloroethylene under ultraviolet illumination gave two products identified as 1-bromo-2,2-dichloroethane and 1-bromo-2,2,4,4-tetra-chlorobutane. With deuterium bromide, the corresponding deuterated halides were formed. 1-Chloroethene-1-d was prepared from 1-bromo-2,2-dichloroethane-2-d.

  在紫外线照射下将溴化氢加入 1,1-二氯乙烯中，得到两种产物，分别为 1-溴-2,2-二氯乙烷和 1-溴-2,2,4,4-四氯丁烷。使用溴化氘，形成相应的氘代卤化物。1-Chloroethene-1-d 由 1-bromo-2,2-dichloroethane-2-d 制备。
• Unimolecular Reactions of CH₂BrCH₂Br, CH₂BrCH₂Cl, and CH₂BrCD₂Cl: Identification of the Cl−Br Interchange Reaction
  作者：Laura Friederich、Juliana R. Duncan、George L. Heard、D. W. Setser、Bert E. Holmes

  DOI：10.1021/jp9116134

  日期：2010.4.1

  respectively, for HBr and HCl elimination from C2H4BrCl. The Br−Cl interchange reaction was demonstrated and characterized by studying the CH2BrCD2Cl system generated by the recombination of CH2Br and CD2Cl radicals. The interchange reaction was identified from the elimination of HBr and DCl from CH2ClCD2Br. The interchange reaction rate is much faster than the rates of either DBr or HCl elimination

  CH 2 Br和CH 2 Cl自由基的重组反应已用于在室温浴气体中产生能量为91 kcal mol -1的振动激发的CH 2 BrCH 2 Br和CH 2 BrCH 2 Cl分子。将用于消除HBr和HCl的实验单分子速率常数与计算出的统计速率常数进行比较，以分别指定从C 2 H 4 Br 2和58 kcal mol -1消除HBr的阈值能量58 kcal mol -1。从C 2 H 4中除去HBr和HCl溴化钾。通过研究由CH 2 Br和CD 2 Cl自由基复合产生的CH 2 BrCD 2 Cl体系，证明并表征了Br-Cl交换反应。通过从CH 2 ClCD 2 Br中消除HBr和DC1来确定交换反应。交换反应速率比从CH 2 BrCD 2 Cl中除去DBr或HCl的速率快得多，阈值能量energy43 kcal mol -1被分配给交换反应。统计速率常数是从过渡态模型中计算出来的，这些模型
• Synthesis and reactions of deuterated 2-(alkylimino)-3-nitrosooxazolidines, 3-alkyl-1-(2-hydroxyethyl)-1-nitrosoureas, and related compounds as possible intermediates in the aqueous decomposition of 3-alkyl-1-(2-chloroethyl)-1-nitrosoureas
  作者：J. William Lown、Shive M. S. Chauhan

  DOI：10.1021/jo00325a011

  日期：1981.6
• LOWN J. W.; CHAUHAN S. M. S., J. ORG. CHEM., 1981, 46, NO 12, 2479-2489
  作者：LOWN J. W.、 CHAUHAN S. M. S.

  DOI：——

  日期：——