1,3-dimethyltetrazolinium tetrafluoroborate | 889098-70-8

• 英文名称: 1,3-dimethyltetrazolinium tetrafluoroborate
• 英文别名: 1,4-dimethyl-tetrazolium tetrafluoroborate；[1,4-dimethyltetrazolium]BF4
• CAS: 889098-70-8
• 化学式: BF₄*C₃H₇N₄
• 分子量: 185.92
• InChiKey: WXENAYOQGXTNOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1,3-dimethyltetrazolinium tetrafluoroborate 在 Amberlite IRA-400 (Cl) Resin 作用下， 以 水 为溶剂， 以72.2%的产率得到1,4-dimethyl-tetrazolium chloride
  参考文献：
  名称：

  Synthesis and Comparison of Transition Metal Complexes of Abnormal and Normal Tetrazolylidenes: A Neglected Ligand Species

  摘要：

  To date, only few examples of tetrazolylidene carbenes coordinated to transition metal complexes have been described. A direct comparison of "normal" tetrazolylidenes (1,4-substitution pattern) and "abnormal" tetrazolylidenes (also referred to as "mesoionic carbenes"; 1,3-substitution pattern) has not been performed at all. In this work, we describe coordination of both ligand types to a row of transition metals. For example, the first examples of tetrazolylidene Mo, Ag, or Ir complexes have been isolated and fully characterized. The mesoionic tetrazolylidene Ag compound 2d is shown to be a viable carbene transfer reagent. By means of NMR, IR, and Raman spectroscopy, as well as X-ray crystallography and computational results, the pronounced differences between the two ligand substitution patterns are highlighted. It is shown that simply changing the position of a methyl group from N3 to N4 in the heterocycle can cause enormous differences in ligand characteristics.

  DOI：

  10.1021/ic4005449
• 作为产物：
  描述：

  1-甲基-1H-四唑 、 trimethoxonium tetrafluoroborate 以 二氯甲烷 为溶剂， 反应 1.67h， 以75.2%的产率得到1,3-dimethyltetrazolinium tetrafluoroborate
  参考文献：
  名称：

  Synthesis and Comparison of Transition Metal Complexes of Abnormal and Normal Tetrazolylidenes: A Neglected Ligand Species

  摘要：

  To date, only few examples of tetrazolylidene carbenes coordinated to transition metal complexes have been described. A direct comparison of "normal" tetrazolylidenes (1,4-substitution pattern) and "abnormal" tetrazolylidenes (also referred to as "mesoionic carbenes"; 1,3-substitution pattern) has not been performed at all. In this work, we describe coordination of both ligand types to a row of transition metals. For example, the first examples of tetrazolylidene Mo, Ag, or Ir complexes have been isolated and fully characterized. The mesoionic tetrazolylidene Ag compound 2d is shown to be a viable carbene transfer reagent. By means of NMR, IR, and Raman spectroscopy, as well as X-ray crystallography and computational results, the pronounced differences between the two ligand substitution patterns are highlighted. It is shown that simply changing the position of a methyl group from N3 to N4 in the heterocycle can cause enormous differences in ligand characteristics.

  DOI：

  10.1021/ic4005449

文献信息

• Tetrazole and triazole carbene complexes of group 6 metal carbonyls
  作者：Guido D. Frey、Karl Öfele、Herbert G. Krist、Eberhardt Herdtweck、Wolfgang A. Herrmann

  DOI：10.1016/j.ica.2005.09.049

  日期：2006.6

  In order to study the relative stability of cis- and trans-isomers of bis(NHC)tetracarbonyl complexes of group 6 metals, we synthesized the corresponding complexes with triazolin- and tetrazolinylidene ligands. By reaction of the free carbene (L = 1,3,4-triphenyl-4,5-dihydro-1H-1,2,4-triazolin-5-ylidene)-first synthesized by Enders - with the hexacarbonyls of Cr, Mo and W the corresponding M(L)(CO)(5) complexes are generated. Depending on an excess of carbene also the cis-(L)(2)Mo(CO)(4) complex was obtained. The latter can be photolytically converted to the trans-(L)(2)Mo(CO)(4) complex. The corresponding complexes with the 1,4-dimethyltetrazolin-5-ylidene ligand (L'), Cr(L')(CO)(5), cis-(L')(2)Cr(CO)(4) and trans-(L')(2)Cr(CO)(4) can be obtained by reaction of hexacarbonyl-mu-trihydroxy-dichromate with dimethyltetrazolium salt. In the cis-(L')(2)Cr(CO)(4) complex, one carbonyl ligand can be replaced by donor ligands such as pyridine or phenylisocyanide to form sym-mer-tricarbonyl complexes. All new complexes are fully characterized by spectroscopy and most by single-crystal X-ray analysis. (c) 2005 Elsevier B.V. All rights reserved.
• <i>N</i>-Heterocyclic Carbenes:  Synthesis, Structures, and Electronic Ligand Properties^,
  作者：Wolfgang A. Herrmann、Jan Schütz、Guido D. Frey、Eberhardt Herdtweck

  DOI：10.1021/om0600801

  日期：2006.5.1

  N-Heterocyclic carbene (NHC) rhodium(l) complexes of general formula Rh(COD)X(NHC) are synthesized and structurally characterized (spectroscopy, X-ray diffraction). The relative sigma-donor/pi-acceptor quality of various NHC ligands was examined and classified by means of IR spectroscopy at the corresponding Rh(CO)(2)I(NHC) complexes. The first single-crystal X-ray diffraction studies of rhodium pyrazolin- and tetrazolinylidene complexes are reported. A wide variety of different azolium salts was applied to obtain rhodium and iridium complexes with two and four carbene ligands.