The Synthesis of η-1,2,3,4,5,6-Hexafluorocyclohexane (Benzene Hexafluoride) from Benzene

被引:15
作者
Durie, Alastair J. [1 ]
Slawin, Alexandra M. Z. [1 ]
Lebl, Tomas [1 ]
O'Hagan, David [1 ]
机构
[1] Univ St Andrews, EaStChem Sch Chem, St Andrews KY16 9ST, Fife, Scotland
基金
英国工程与自然科学研究理事会;
关键词
benzene hexafluoride; conformational analysis; hexafluorocyclohexane; organofluorine chemistry; FLUORINE; SULFATES; COMPLEX; BONDS;
D O I
10.1002/anie.201205577
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Six of the best: Benzene had been used by Faraday and Mitscherlich in their respective synthesis of hexachloro- and hexabromocyclohexane in the early 19th century. Also starting from benzene, η-1,2,3,4,5,6- hexafluorocyclohexane (benzene hexafluoride; see X-ray structure of a dimer) was now synthesized in five steps. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:10086 / 10088
页数:3
相关论文
共 24 条
[11]   VICINAL DIOL CYCLIC SULFATES - LIKE EPOXIDES ONLY MORE REACTIVE [J].
GAO, Y ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7538-7539
[12]   Facile synthesis of 4-deoxy-4-fluoro-α-D-talopyranoside, 4-deoxy-4-fluoro-α-D-idopyranoside and 2,4-dideoxy-2,4-difluoro-α-D-talopyranoside [J].
Giuffredi, Guy T. ;
Jennings, Laura E. ;
Bernet, Bruno ;
Gouverneur, Veronique .
JOURNAL OF FLUORINE CHEMISTRY, 2011, 132 (10) :772-778
[13]   How good is fluorine as a hydrogen bond acceptor? [J].
Howard, JAK ;
Hoy, VJ ;
OHagan, D ;
Smith, GT .
TETRAHEDRON, 1996, 52 (38) :12613-12622
[14]  
Hunter L., 2009, ANGEW CHEM, V121, P5565
[15]   Synthesis and Structure of Stereoisomeric Multivicinal Hexafluoroalkanes [J].
Hunter, Luke ;
Kirsch, Peer ;
Slawin, Alexandra M. Z. ;
O'Hagan, David .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (30) :5457-5460
[16]   Characterization of a closed-shell fluorine-fluorine bonding interaction in aromatic compounds on the basis of the electron density [J].
Matta, CF ;
Castillo, N ;
Boyd, RJ .
JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (16) :3669-3681
[17]  
Matthews F. E., 1892, J CHEM SOC, V61, P103
[18]  
Mitscherlich E., 1835, ANN PHYS, V111, P370
[19]   Organofluorine Chemistry: Synthesis and Conformation of Vicinal Fluoromethylene Motifs [J].
O'Hagan, David .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08) :3689-3699
[20]   APPLICATION OF 2-DIMENSIONAL NMR TO KINETICS OF CHEMICAL-EXCHANGE [J].
PERRIN, CL ;
DWYER, TJ .
CHEMICAL REVIEWS, 1990, 90 (06) :935-967