dimethylphenyl sulfonium tetrafluoroborate | 33613-52-4

• 英文名称: dimethylphenyl sulfonium tetrafluoroborate
• 英文别名: dimethyl(phenyl)sulfonium tetrafluoroborate；dimethylphenylsulfonium tetrafluoroborate；phenyldimethylsulfonium tetrafluoroborate；tetrafluoroborate de diphenylsulfonium
• CAS: 33613-52-4
• 化学式: BF₄*C₈H₁₁S
• 分子量: 226.046
• InChiKey: DDPHVXKLGBUIJR-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：

  dimethylphenyl sulfonium tetrafluoroborate 在 吡啶 作用下， 以 氘代甲醇 为溶剂， 生成 茴香硫醚
  参考文献：
  名称：

  Reactivity of Substituted Phenyldimethylsulfonium Ions with Common Nucleophiles. A Test of pK_lg^Me for Phenyldimethylsulfonium Salts and a Comparison with Methyl Arenesulfonates

  摘要：

  The correlations of nucleophilic rate data for phenyldimethylsulfonium ions with common nucleophiles with pK(lg)(Me) values shows that the slopes of the line, beta(lg)(Me), correlate qualitatively with Edwards hardness parameter for the nucleophile, and not with the Swain-Scott n(o) parameter. Comparison with substituted methyl arenesulfonates shows different leaving group behavior in the two systems. These results support Shaik's hypothesis that leaving group behavior consists of some SET character.

  DOI：

  10.1021/jo9618233
• 作为产物：
  描述：

  茴香硫醚 、 trimethoxonium tetrafluoroborate 以 丙酮 为溶剂， 反应 0.25h， 生成 dimethylphenyl sulfonium tetrafluoroborate
  参考文献：
  名称：

  乙烯基sulf作为新型蛋白水解酶抑制剂。

  摘要：

  乙烯基sulf是由甲基硫化物通过甲基化合成的，并抑制蛋白水解酶木瓜蛋白酶。抑制研究表明，乙烯基sulf抑制剂可以共价和不可逆地修饰酶。

  DOI：

  10.1016/s0960-894x(01)00440-1
• 作为试剂：
  描述：

  benzoyl(7-bromo-3,4-dihydroisoquinolin-2-ium-2-yl)amide 在 六甲基磷酰三胺 、 dimethylphenyl sulfonium tetrafluoroborate 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以80%的产率得到10-bromo-3-phenyl-6,7-dihydro-1H-1,5-methanobenzo[g][1,3,4]oxadiazonine
  参考文献：
  名称：

  Ring Enlargement Reaction of C,N-Cyclic-N′-acyl Azomethine Imines with Sulfonium Ylide: An Efficient Synthesis of 3-Benzazepine Derivatives

  摘要：

  Highly efficient formation of 3-benzazepine derivatives has been achieved, based on the ring expansion reaction of C,N-cyclic-N'-acyl azomethine imines with sulfonium ylide generated in situ from the corresponding sulfonium salt. The reactions proceeded smoothly to afford the tricyclic 3-benzazepine derivatives in good to high yields. A wide range of C,N-cyclic N'-acyl azomethine imines were applicable to this reaction.

  DOI：

  10.1021/ol502347n

文献信息

• Synthesis of 1-alkynyl(diphenyl)onium salts of group 16 elements via heteroatom transfer reaction of 1-alkynyl(phenyl)-λ3-iodanes
  作者：Masahito Ochiai、Takema Nagaoka、Takuya Sueda、Jie Yan、Da-Wei Chen、Kazunori Miyamoto

  DOI：10.1039/b212512a

  日期：2003.4.23

  1-Alkynyl(phenyl)-lambda 3-iodanes undergo selective transfer of the alkynyl groups over the phenyl group onto diphenyl chalcogens. Exposure of 1-alkynyl(phenyl)-lambda 3-iodanes to diphenyl chalcogens (S, Se, and Te) in dichloromethane or 1,2-dichloroethane affords 1-alkynyl(diphenyl)sulfonium, -selenonium, and -telluronium salts in high yields.

  1-炔基（苯基）-λ3-碘经过烷基上的炔基选择性转移到二苯基硫属元素上。将1-炔基（苯基）-λ3-碘暴露于二氯甲烷或1,2-二氯乙烷中的二苯基硫属元素（S，Se和Te）中，可以得到高浓度的1-炔基（二苯基）ulf，-硒和-碲金属盐产量。
• The use of sulfur ylides in the synthesis of 3-alkyl(aryl)thio-4-trifluoromethylpyrroles from mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates
  作者：Ryosuke Saijo、Masami Kawase

  DOI：10.1016/j.tetlet.2012.03.130

  日期：2012.5

  In this report, we describe a new method for the synthesis of densely functionalized pyrroles. Reaction of mesoionic 1,3-oxazolium-5-olates with various S-ylides proceeds via nucleophilic addition followed by opening of the oxazole ring and subsequent cyclization to multisubstituted pyrroles bearing both a trifluoromethyl and alkyl(aryl)thio group at 3- and 4-positions.

  在这份报告中，我们描述了一种合成高密度官能化吡咯的新方法。通过亲核加成反应，使中离子1,3-恶唑基5-油酸酯与各种S-基化物反应，然后打开恶唑环，随后环化成在3-和4位同时带有三氟甲基和烷基（芳基）硫基的多取代吡咯-位置。
• α-Effect with Substituted <i>N</i>-Methylbenzohydroxamates and Substituted Phenyldimethylsulfonium Salts:  Toward Understanding of an Intrinsic α-Effect
  作者：K. R. Fountain、Timothy W. Dunkin、Kamlesh D. Patel

  DOI：10.1021/jo9620021

  日期：1997.5.1

  ium ions decreases the alpha-effect for the methyl transfers toward 1.0 (zero effect). An extrapolation shows the possibility of an inverse effect (<1.0). The reactivity of G-NMBH anions correlates with SET parameters and with the known propensity of phenyldimethylsulfonium ions to accept a single electron into a sigma C-S orbital concomitant with expulsion of a CH(3) group. These correlations indicate

  在G-NMBH阴离子与取代的苯基二甲基s离子反应中，电子需求的增加降低了甲基转移至1.0的α效应（零效应）。外推表明存在反作用的可能性（<1.0）。G-NMBH阴离子的反应性与SET参数相关，并且与已知的苯基二甲基s离子接受单个电子进入σCH轨道并伴随CH（3）排出的倾向有关。这些相关性表明，对于这些反应，在S（N）2跃迁状态的波函数中包含一些SET字符，这与S（N）2反应的Shaik和Pross SCD模型一致。
• McCurdy, Alison; Jimenez, Leslie; Stauffer, David A., Journal of the American Chemical Society, 1992, vol. 114, # 26, p. 10314 - 10321
  作者：McCurdy, Alison、Jimenez, Leslie、Stauffer, David A.、Dougherty, Dennis A.

  DOI：——

  日期：——
• Correlations of p<i>K</i>_lg^Me with Reduction Potentials
  作者：K. R. Fountain、Kamlesh D. Patel、Timothy W. Dunkin、Janette A. Powers、Dean A. Van Galen

  DOI：10.1021/jo961658r

  日期：1997.2.1

  The quantitative indices for the ability of leaving groups to depart from C atoms are pK(lg)(Me). In the cases of methyl transfers from arenesulfonates, these parameters have correlated a large number of nucleophilic data. A new scale of these parameters has been defined from methyl transfer data between phenylmethyl thioethers. The pK(lg)(Me) data from both sets of compounds correlated with both experimental E(1/2) values and E(LUMO) values from computational chemistry. These correlations support the SCM model of Shaik et al. which requires the leaving group to display some SET character in an S(N)2 transition state.