cis-heptafluorobut-1-en-1yldifluoroborane | 375856-38-5

• 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: cis-heptafluorobut-1-en-1yldifluoroborane
• 英文别名: perfluoro-cis-but-1-enyldifluoroborane；cis-perfluorobut-1-enyldifluoroborane；cis-C2F5CF=CFBF2；difluoro-[(Z)-1,2,3,3,4,4,4-heptafluorobut-1-enyl]borane
• CAS: 375856-38-5
• 化学式: C₄BF₉
• 分子量: 229.841
• InChiKey: LCEWVTIMIQWKDJ-UPHRSURJSA-N

物化性质

• 沸点：
  30.8±45.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  二氟代氙 、 cis-heptafluorobut-1-en-1yldifluoroborane 以 further solvent(s) 为溶剂， 以22%的产率得到[cis-C2F5CF=CFXe][C4F9BF3]
  参考文献：
  名称：

  Alk-1-enylxenonium(II) 和 Alk-1-ynylxenonium(II) 盐 [RXe]Y 与溴化物和碘化物在无水 HF 中的反应

  摘要：

  在烯基氙 (II) 盐 [RCF=CFXe]Y（R = 顺式-C2F5，反式-H）和炔基氙（II）盐 [C3F7C≡CXe][BF4] 与 NaI 的反应中用碘替代氙（+）在无水 HF (aHF) 中发生区域特异性。在 -60 °C 下，氙 (+) 被全氟化盐 [cis-CF3CF=CFXe]Y 和 [trans-C4F9CF=CFXe]Y 中的溴取代，在 aHF 中与 NaBr 进行区域和立体定向，但在更高的温度下并且在较长时间后，在 aHF 中用 NaBr、KBr 或 [NBu4]Br 处理 [cis-C2F5CF=CFXe]Y，得到顺式和反式-全氟丁-1-烯基溴化物的混合物。[C3F7C≡CXe][BF4]与NaBr在-65°C的aHF中的反应仅产生48%的C3F7C≡CBr，并伴有含溴相关烯烃的混合物。讨论了主要产物的反应途径。

  DOI：

  10.1002/zaac.200700075
• 作为产物：
  描述：

  potassium trifluoro(cis-heptafluorobut-1-en-1-yl)borate 在 三氟化硼 作用下， 以 二氯甲烷 为溶剂， 生成 cis-heptafluorobut-1-en-1yldifluoroborane
  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

• Bis(perfluoroorganyl)bromonium salts [(RF)2Br]Y (RF=aryl, alkenyl, and alkynyl)
  作者：Hermann-Josef Frohn、Matthias Giesen、Dirk Welting、Vadim V. Bardin

  DOI：10.1016/j.jfluchem.2010.06.006

  日期：2010.9

  Bromonium salts [(RF)2Br]Y with perfluorinated groups RFC6F5, CF3CFCF, C2F5CFCF, and CF3C≡C were isolated from reactions of BrF3 with RFBF2 in weakly coordinating solvents (wcs) like CF3CH2CHF2 (PFP) or CF3CH2CF2CH3 (PFB) in 30–90% yields. C6F5BF2 formed independent of the stoichiometry only [(C6F5)2Br][BF4]. 1:2 reactions of BrF3 and silanes C6F5SiY3 (Y = F, Me) ended with different products – C6F5BrF2

  溴鎓盐[（R ˚F）2溴- ] Y与全氟化基团- [R ˚F Ç 6 ˚F 5，CF 3 CF CF，C 2 ˚F 5 CF CF，和CF 3 C≡C，从BRF的反应分离出3，其中R ˚F BF 2在弱配位溶剂（wcs）中，例如CF 3 CH 2 CHF 2（PFP）或CF 3 CH 2 CF 2 CH 3（PFB），收率30-90％。C 6 F 5高炉2仅仅与化学计量无关地形成[[C 6 F 5）2 Br] [BF 4 ]。BrF 3与硅烷C 6 F 5 SiY 3（Y = F，Me）的1：2反应以不同的产物– C 6 F 5 BrF 2或[（C 6 F 5）2 Br] [SiF 5 ] –终止纯的个体，取决于Y和反应温度（Y = F）。在≥−30°C时使用C 6 F 5 SiF 3 [[C 6 F 5）2 Br] [SiF5 ]导致产率为92％，而具有较少路易斯酸性C 6 F 5 SiMe
• 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
• (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.
• (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.
• Reactions of Alk-1-enylxenonium(II) and Alk-1-ynylxenonium(II) Salts [RXe]Y with Bromides and Iodides in Anhydrous HF
  作者：Hermann-Josef Frohn、Vadim V. Bardin

  DOI：10.1002/zaac.200700075

  日期：2007.8

  The replacement of xenon(+) by iodine in reactions of alkenylxenonium(II) salts [RCF=CFXe]Y (R = cis-C2F5, trans-H) and alkynylxenonium(II) salt [C3F7C≡CXe][BF4] with NaI in anhydrous HF (aHF) occurred regiospecifically. At −60 °C the substitution of xenon(+) by bromine in the perfluorinated salts [cis-CF3CF=CFXe]Y and [trans-C4F9CF=CFXe]Y proceeded regio- and stereospecifically with NaBr in aHF, but

  在烯基氙 (II) 盐 [RCF=CFXe]Y（R = 顺式-C2F5，反式-H）和炔基氙（II）盐 [C3F7C≡CXe][BF4] 与 NaI 的反应中用碘替代氙（+）在无水 HF (aHF) 中发生区域特异性。在 -60 °C 下，氙 (+) 被全氟化盐 [cis-CF3CF=CFXe]Y 和 [trans-C4F9CF=CFXe]Y 中的溴取代，在 aHF 中与 NaBr 进行区域和立体定向，但在更高的温度下并且在较长时间后，在 aHF 中用 NaBr、KBr 或 [NBu4]Br 处理 [cis-C2F5CF=CFXe]Y，得到顺式和反式-全氟丁-1-烯基溴化物的混合物。[C3F7C≡CXe][BF4]与NaBr在-65°C的aHF中的反应仅产生48%的C3F7C≡CBr，并伴有含溴相关烯烃的混合物。讨论了主要产物的反应途径。