Perfluoroorganylxenonium(II) salts from reactions of XeF2 or [FXe][SbF6] with selected perfluorinated alk-1-yn-1-yl- and alk-1-en-1-yltrifluoroborate salts in aHF

被引:1
作者
Bardin, Vadim V. [2 ]
Frohn, Hermann-Josef [1 ]
机构
[1] Univ Duisburg Essen, D-47048 Duisburg, Germany
[2] SB RAS, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
关键词
Alkynylxenonium(II) salts; Alkenylxenonium(II) salts; Alkynyltrifluoroborate salts; Alkenyltrifluoroborate salts; Xenodeboration; Hydrodeboration; NMR spectroscopy; XENON-CARBON BOND; HYDROGEN-FLUORIDE; ELECTROPHILIC OXYGENATION; HYDROCARBON ANALOGS; METHODICAL APPROACH; NMR-SPECTRA; REACTIVITY; (FLUOROORGANO)FLUOROBORANES; DIFLUORIDE; PERFLUOROALKYL;
D O I
10.1016/j.jfluchem.2012.03.014
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Xenon difluoride reacted with alkynylborate salts, K[RFC CBF3], in anhydrous HF (aHF) to give alkynylxenonium salts, [RFC CXe][BF4] (R-F = CF3, C3F7, (CF3)(2)CF), in 50-55% yield. Both [FXe][SbF6] and K[C3F7C CBF3] formed the [C3F7C CXe](+) salt in aHF. In the reaction of XeF2 with the alkenylborate salt, K[CF2=C(CF3)BF3], the competitive hydrodeboration reaction (formation of CF2=C(CF3)H in 85% yield) exceeded the xenodeboration reaction (formation of the xenonium salt [CF2=C(CF3)Xe][BF4] in 15% yield only). K[4-BF3C5F4N] did not react with XeF2 in aHF, but underwent fluorine addition in the presence of AsF5. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:28 / 33
页数:6
相关论文
共 27 条
[1]   Polyfluoroorganotrifluoroborates and -difluoroboranes: interesting materials in fluoroorgano and fluoroorgano-element chemistry [J].
Abo-Amer, A ;
Adonin, NY ;
Bardin, VV ;
Fritzen, P ;
Frohn, HJ ;
Steinberg, C .
JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (11) :1771-1778
[2]   From hypervalent xenon difluoride and aryliodine(III) difluorides to onium salts: Scope and limitation of acidic fluoroorganic reagents in the synthesis of fluoroorgano xenon(II) and iodine(III) onium salts [J].
Abo-Amer, Anwar ;
Frohn, Hermann-Josef ;
Steinberg, Christoph ;
Westphal, Ulrich .
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (10) :1311-1323
[3]   The effect of N-heterocyclic carbene ligands in the palladium-catalyzed cross-coupling reaction of K[C6F5BF3] with aryl iodides and aryl bromides [J].
Adonin, Nicolay Yu. ;
Babushkin, Dmitrii E. ;
Parmon, Valentin N. ;
Bardin, Vadim V. ;
Kostin, Gennadiy A. ;
Mashukov, Vasiliy I. ;
Frohn, Hermann-Josef .
TETRAHEDRON, 2008, 64 (25) :5920-5924
[4]   Reactions of Perfluorinated Alkenyl-, Alkynyl-, Alkyltrifluoroborates, and Selected Hydrocarbon Analogues with the Halogenating Agents Hal2 (Hal = F, Cl, Br), "BrF" (BrF3-Br2 1:1), and ICl [J].
Bardin, Vadim V. ;
Adonin, Nicolay Yu ;
Frohn, Hermann-Josef .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2012, 638 (3-4) :565-579
[5]   Reactions of fluoroalk-1-en-1-yltrifluoroborate and perfluoroalk-1-yn-1-yltrifluoroborate salts and selected hydrocarbon analogues with hydrogen fluoride and with halogenating agents in aHF and in basic solvents [J].
Bardin, Vadim V. ;
Adonin, Nicolay Yu. ;
Frohn, Hermann-Josef .
JOURNAL OF FLUORINE CHEMISTRY, 2012, 135 :114-128
[6]   (Fluoroorgano)fluoroboranes and -borates.: 14.: Preparation of potassium ((perfluoroorgano)ethynyl)trifluoroborates K[RFC=CBF3] [J].
Bardin, VV ;
Adonin, NY ;
Frohn, HJ .
ORGANOMETALLICS, 2005, 24 (22) :5311-5317
[7]  
Bardin VV, 2002, Z ANORG ALLG CHEM, V628, P883, DOI 10.1002/1521-3749(200205)628:4<883::AID-ZAAC883>3.0.CO
[8]  
2-A
[9]  
Bardin VV, 2002, MAIN GROUP MET CHEM, V25, P589
[10]   THE FLUORO(PERFLUOROPYRIDINE)XENON(II) CATIONS, C5F5N-XEF+ AND 4-CF3C5F4N-XEF+ - NOVEL EXAMPLES OF XENON AS AN AROMATIC SUBSTITUENT AND OF XENON-NITROGEN BONDING [J].
EMARA, AAA ;
SCHROBILGEN, GJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) :257-259