Regiospecific fluorination of the aryl group in C6F5I and the preparation of C6F7IF2 - The first perfluorovinyl iodine(III) compound

被引：7

作者：

Frohn, HJ

Nielinger, R

机构：

[1] Fachgebiet Anorganische Chemie, Gerhard-Mercator-Univ. Duisburg, D-47048 Duisburg

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1996年 / 77卷 / 02期

关键词：

pentafluoroiodobenzene; 1-iodoheptafluoro-1,4-cyclohexadiene; 1-difluoroiodoheptafluoro-1,4-cyclohexadiene; 1-acetoxy(fluoro)iodo-heptafluoro-1; -4-cyclohexadiene; iodine pentafluoride; fluorination; NMR spectroscopy; IR spectroscopy; mass spectrometry;

D O I：

10.1016/0022-1139(96)03399-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Pentafluoroiodobenzene was oxidized regiospecificly by IF5/BF3 in CH2Cl2 to 1-iodo-heptafluoro-1,4-cyclohexadiene. With bromo- and chloro-pentafluorobenzene as substrates, the addition of two fluorine atoms to the aromatic ring proceeded analogously but more slowly. 1-Iodo-heptafluoro-1,4-cyclohexadiene was converted to 1-difluoroiodo-heptafluoro-1,4-cyclohexadiene by low-temperature fluorination. The thermal stability and reactivity of the first example of a perfluorinated vinyl iodine(III) compound are reported.

引用

页码：143 / 146

页数：4

共 24 条

[1] PENTAFLUOROPHENYLIODINE(V) COMPOUNDS .2. PENTAFLUOROPHENYLIODINE TETRAFLUORIDE C6F5IF4 - SYNTHESIS VIA FLUORINE-ARYL-SUBSTITUTION ON IF5 - PROPERTIES AND STRUCTURE - STRUCTURAL-ANALYSIS OF THE MONOVALENT IODINE PARENT COMPOUND C6F5I
FROHN, HJ
GORG, S
HENKEL, G
LAGE, M
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1995, 621 (07): : 1251 - 1256
[2] A widely varying range of products in reactions of C6F5BrF2, C6F5IF2, and C6F5IF4 with Lewis acids of different strength
Frohn, Hermann-Josef
Bailly, Frank
Welting, Dirk
Bardin, Vadim V.
JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (03) : 301 - 307
[3] [(C6F5)2IF2][BF4], the first salt with the electrophilic cation [(C6F5)2IF2]+:: Synthesis, reactivity, and structure
Frohn, Hermann-Josef
Wenda, Andre
Floerke, Ulrich
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2008, 634 (04): : 764 - 770
[4] Synthesis and molecular structures of heptafluoroisopropylated fullerenes: C60(i-C3F7)8, C60(i-C3F7)6, and C60(CF3)2(i-C3F7)2
Mutig, Tatyana
Avdoshenko, Stanislav M.
Kemnitz, Erhard
Troyanov, Sergey I.
JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (02) : 241 - 247
[5] Xenon(IV)-Carbon Bond of [C6F5XeF2]+; Structural Characterization and Bonding of [C6F5XeF2][BF4], [C6F5XeF2}[BF4]•2HF, and [C6F5XeF2][BF4]•nNCCH 3 (n=1, 2); and the Fluorinating Properties of [C6F5XeF2][BF4]
Koppe, Karsten
Haner, Jamie
Mercier, Helene P. A.
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INORGANIC CHEMISTRY, 2014, 53 (21) : 11640 - 11661
[6] Fluorination/Dearomatization of C6F5 Groups: An FLP Route to an Electrophilic Borane and Non-Coordinating Anions
Kim, Hyehwang
Mandal, Dipendu
Ng, Joshua Kye Jin
Qu, Zheng-Wang
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CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (43)
[7] Thermal decomposition of 4-fluorobenzenediazonium perfluoroorganyl(fluoro)borates, [4-FC6H4N2]Y (Y = RFBF3 (RF = C6F5, C6F13, trans-C4F9CF=CF, cis-C6F13CF=CF, CF3CC) and (C6F13)2BF2)
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[8] Bis(pentafluorophenyl)xenon, Xe(C6F5)2:: A homoleptic diorganoxenon derivative
Maggiarosa, N
Naumann, D
Tyrra, W
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (24) : 4588 - +
[9] Formation and characterization of zwitterionic stereoisomers from the reaction of B(C6F5)3 and NEt2Ph:: (E)- and (Z)-[EtPhN+=CHCH2-B-(C6F5)3]
Millot, N
Santini, CC
Fenet, B
Basset, JM
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2002, (12) : 3328 - 3335
[10] Thermoanalytical and preparative investigations of the decomposition of potassium perfluoroorganyl(fluoro)borate salts, K[RFBF3] (RF = perfluoroalkyl, -alkenyl, -alkynyl, and -aryl groups) and K[(RF)2BF2] (RF = C6F5 and C6F13)
Bardin, Vadim V.
Shundrina, Inna K.
Frohn, Hermann-Josef
JOURNAL OF FLUORINE CHEMISTRY, 2014, 157 : 73 - 78

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