perfluoro-trans-hex-1-enyldifluoroborane | 375856-42-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: perfluoro-trans-hex-1-enyldifluoroborane
• 英文别名: trans-perfluorohex-1-enyldifluoroborane；difluoro-[(E)-1,2,3,3,4,4,5,5,6,6,6-undecafluorohex-1-enyl]borane
• CAS: 375856-42-1
• 化学式: C₆BF₁₃
• 分子量: 329.856
• InChiKey: BEBZEMINVMISJD-OWOJBTEDSA-N

物化性质

• 沸点：
  83.3±50.0 °C(Predicted)
• 密度：
  1.543±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  二氟代氙 、 perfluoro-trans-hex-1-enyldifluoroborane 以 氢氟酸 为溶剂， 以99%的产率得到fluoronium trifluoro(perfluorohexyl)borate
  参考文献：
  名称：

  (Fluoroorgano)fluoroboranes and -borates. 7 [1] The Reaction of RFBF2 and K [RFBF3] (RF = perfluorophenyl-, perfluoroalk-1-enyl- and perfluoroalkyl) with Xenon Difluoride in Anhydrous HFDedicated to Professor Dieter Naumann on the Occasion of his 60th Birthday

  摘要：

  The dissolution of (perfluoroorgano)difluoroboranes RFBF2 in anhydrous HF (aHF) resulted in equilibrium mixtures of the starting borane and different kinds of acid-base products: [H2F] [RFBF2(F.HF)] (R-F=C6F5, cis-C2F5CF=CF, trans-C4F9CF=CF) or [H2F] [RFBF3] (RF=C6F13). In aHF the aryl compounds C6F5BF2 and K [C6F5BF3] showed two parallel reactivities with XeF2: xenodeborylation (formation of the [C6F5Xe](+) cation) and fluorine addition to the aryl group. In aHF perfluoroalk-1-enyldifluoroboranes RFBF2 as well as potassium perfluoroalk-1-enyltrifluoroborates K [RFBF3] (R-F=cis-C2F5CF=CF, trans-C4F9CF=CF) underwent only fluorine addition across the carbon-carbon double bond under the action of XeF2. Potassium perfluorohexyl-trifluoroborate K [C6F13BF3] did not react with XeF2 in aHF.

  DOI：

  10.1002/1521-3749(200208)628:8<1853::aid-zaac1853>3.0.co;2-m
• 作为产物：
  描述：

  potassium perfluoro-trans-hex-1-enyltrifluoroborate 在 三氟化硼 作用下， 以 二氯甲烷 为溶剂， 生成 perfluoro-trans-hex-1-enyldifluoroborane
  参考文献：
  名称：

  (Fluoroorgano)fluoroboranes and -fluoroborates

  摘要：

  Polyfluoroalken-1-yldifluoroboranes RCF=CFBF2 (R = F, cis-, trans-Cl, trans-C4F9, cis-C2F5, cis-C6F13, trans-C4H9, trans-C6H5) were prepared by defluoridation of the corresponding fluoroborate salts K[RCF=CFBF3] using boron trifluoride in dichloromethane or fluorotrichloromethane. The alkenylboranes were characterised by H-1-, B-11- and F-19-NMR spectroscopy. Their reactivity towards ether, water and anhydrous HF was investigated. (C) 2001 Elsevier Science V.B. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00858-0

文献信息

• The Reaction of 2-X-1, 2-Difluoroalk-1-enyldifluoroboranes with Xenon Difluoride. A Methodical Approach to 1, 2-Difluoroalk-1-enylxenon(II) Salts
  作者：Hermann-Josef Frohn、Nicolay Yu. Adonin、Vadim V. Bardin

  DOI：10.1002/zaac.200300234

  日期：2003.12

  2-X-1, 2-Difluoroalk-1-enylxenon(II) salts were prepared by the reaction of XeF2 with XCF=CFBF2 (X = F, trans-H, cis-Cl, trans-Cl, cis-CF3, cis-C2F5) but no organoxenon(II) compounds were obtained when the trans-isomers of boranes, trans-XCF=CFBF2 (X = CF3, C4F9, C4H9, Et3Si), were used under similar conditions. Reaktionen von 2-X-1, 2-Difluoralk-1-enyldifluorboranen mit Xenondifluorid. Untersuchung

  2-X-1, 2-Difluoroalk-1-enylxenon(II) 盐是通过 XeF2 与 XCF=CFBF2 (X = F, trans-H, cis-Cl, trans-Cl, cis-CF3, cis -C2F5) 但在类似条件下使用硼烷的反式异构体反式-XCF=CFBF2 (X = CF3、C4F9、C4H9、Et3Si) 时，没有得到有机氧 (II) 化合物。Reaktionen von 2-X-1, 2-Difluoralk-1-enyldifluorboranen mit Xenondifluorid。Untersuchung des methodischen Zugangs zu 1, 2-Difluoralk-1-enylxenon(II)salzen 2-X-1, 2-Difluoralk-1-enylxenon(II)salze wurden bei der Reaktion
• Thermal decomposition of 4-fluorobenzenediazonium perfluoroorganyl(fluoro)borates, [4-FC6H4N2]Y (Y=RFBF3 (RF=C6F5, C6F13, trans-C4F9CFCF, cis-C6F13CFCF, CF3CC) and (C6F13)2BF2)
  作者：Vadim V. Bardin、Hermann-Josef Frohn

  DOI：10.1016/j.jfluchem.2013.08.001

  日期：2013.12

  Heating of the neat salts [4-FC6H4N2][RFRF3] (R-F = C6F5, C6F13 trans-C4F9CF=CF, cis-C6F13CF=CF, CF3C C or in solid mixtures with NaF gives the principal product 1,4-C6F2H4 besides RFBF2 or Na[RFBF3], respectively. Thermolysis of [4-FC6H4N2][(C6F13)(2)BF2] in NaF results in 1,4-C6F2H4, Na[BF4], Na[(C6F13)(2)BF2], and a new type of product, the isomer Na[C6F13CF(BF3)C5F11]. (C) 2013 Elsevier B.V. All rights reserved.
• Distinct reactivities of cis- and trans-RFCF=CFBF2 towards XeF2 and the first synthesis of a [trans-RFCF=CFXe]+ salt
  作者：Hermann-Josef Frohn、Vadim V. Bardin

  DOI：10.1016/j.mencom.2007.05.001

  日期：2007.5

  The competitive reaction of C4F9CF=CFBF2 (Cis: trans = 1.2: 1) with XeF2 demonstrated for the first time a remarkably lower reaction rate of the trans isomer with respect to the cis isomer in the xenodeborylation reaction (formation of the [C4F9CF=CFXe](+) cation with a cis: trans ratio of 2.5 to 4:1) and allowed us to develop reaction conditions for the syntheses of [trans-C4F9CF=CFXe](+) salts.
• (Fluoroorgano)fluoroboranes and -fluoroborates
  作者：H.-J. Frohn、V.V. Bardin

  DOI：10.1016/s0022-328x(01)00858-0

  日期：2001.8

  Polyfluoroalken-1-yldifluoroboranes RCF=CFBF2 (R = F, cis-, trans-Cl, trans-C4F9, cis-C2F5, cis-C6F13, trans-C4H9, trans-C6H5) were prepared by defluoridation of the corresponding fluoroborate salts K[RCF=CFBF3] using boron trifluoride in dichloromethane or fluorotrichloromethane. The alkenylboranes were characterised by H-1-, B-11- and F-19-NMR spectroscopy. Their reactivity towards ether, water and anhydrous HF was investigated. (C) 2001 Elsevier Science V.B. All rights reserved.
• (Fluoroorgano)fluoroboranes and -borates. 7 [1] The Reaction of RFBF2 and K [RFBF3] (RF = perfluorophenyl-, perfluoroalk-1-enyl- and perfluoroalkyl) with Xenon Difluoride in Anhydrous HFDedicated to Professor Dieter Naumann on the Occasion of his 60th Birthday
  作者：H.-J. Frohn、V. V. Bardin

  DOI：10.1002/1521-3749(200208)628:8<1853::aid-zaac1853>3.0.co;2-m

  日期：2002.8

  The dissolution of (perfluoroorgano)difluoroboranes RFBF2 in anhydrous HF (aHF) resulted in equilibrium mixtures of the starting borane and different kinds of acid-base products: [H2F] [RFBF2(F.HF)] (R-F=C6F5, cis-C2F5CF=CF, trans-C4F9CF=CF) or [H2F] [RFBF3] (RF=C6F13). In aHF the aryl compounds C6F5BF2 and K [C6F5BF3] showed two parallel reactivities with XeF2: xenodeborylation (formation of the [C6F5Xe](+) cation) and fluorine addition to the aryl group. In aHF perfluoroalk-1-enyldifluoroboranes RFBF2 as well as potassium perfluoroalk-1-enyltrifluoroborates K [RFBF3] (R-F=cis-C2F5CF=CF, trans-C4F9CF=CF) underwent only fluorine addition across the carbon-carbon double bond under the action of XeF2. Potassium perfluorohexyl-trifluoroborate K [C6F13BF3] did not react with XeF2 in aHF.