Synthesis and Structure of Stereoisomeric Multivicinal Hexafluoroalkanes

被引：62

作者：

Hunter, Luke ^{[1
,2
]}

Kirsch, Peer ^{[3
]}

Slawin, Alexandra M. Z. ^{[1
,2
]}

O'Hagan, David ^{[1
,2
]}

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

[2] Univ St Andrews, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland

[3] Merck Ltd Japan, New Technol Off, Aikawa, Kanagawa 2430303, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 30期

基金：

英国工程与自然科学研究理事会;

关键词：

conformation analysis; fluorine; organofluorine chemistry; stereochemistry; FLUORINE;

D O I：

10.1002/anie.200901956

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rational expectations: Molecules containing six contiguous fluorine atoms along a carbon backbone have been synthesized in a stereocontrolled manner. X-ray crystallography shows that the fluoroalkane can adopt a helical or a zigzag shape depending on the stereochemical pattern (see structures). These findings are rationalized by simple stereochemical effects associated with C-F bonds. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5457 / 5460

页数：4

共 26 条

[1]

[Anonymous], 2017, J MOL STRUCT, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014

[2] 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

[3] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[4] Gauche effect in 1,2-difluoroethane. Hyperconjugation, bent bonds, steric repulsion [J].

Goodman, L ;

Gu, HB ;

Pophristic, V .

JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (06) :1223-1229

[5]

Gooseman N.E., 2007, Angewandte Chemie, V119, P6008

[6] An electrostatic gauche effect in β-fluoro- and β-hydroxy-N-ethylpyridinium cations [J].

Gooseman, Natalie E. J. ;

O'Hagan, David ;

Peach, Michael J. G. ;

Slawin, Alexandra M. Z. ;

Tozer, David J. ;

Young, Robert J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (31) :5904-5908

[7] The many roles for fluorine in medicinal chemistry [J].

Hagmann, William K. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369

[8] Stereoelectronic and steric effects in the collagen triple helix: Toward a code for strand association [J].

Hodges, JA ;

Raines, RT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15923-15932

[9]

Hunter L., 2007, ANGEW CHEM, V119, P8033

[10] The multi-vicinal fluoroalkane motif: an examination of 2,3,4,5-tetrafluorohexane stereoisomers [J].

Hunter, Luke ;

Kirsch, Peer ;

Hamilton, John T. G. ;

O'Hagan, David .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (17) :3105-3108

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