The multi-vicinal fluoroalkane motif: an examination of 2,3,4,5-tetrafluorohexane stereoisomers

被引：23

作者：

Hunter, Luke ^{[1
,2
]}

Kirsch, Peer ^{[3
]}

Hamilton, John T. G. ^{[4
]}

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

机构：

[1] Univ St Andrews, Ctr Biomol Sci, St Andrews, Fife, Scotland

[2] Univ St Andrews, Sch Chem, St Andrews, Fife, Scotland

[3] Merck Ltd Japan, Liquid Crystal Tech Ctr, Aikawa, Kanagawa 2430303, Japan

[4] Agri Food Biosci Inst, Food Chem Branch, Belfast, Antrim, North Ireland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

Positive ions;

D O I：

10.1039/b807449f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three unique diastereoisomers of 2,3,4,5 -tetrafluorohexane have been prepared, compounds intermediate between hexane and perfluorohexane in their degree of fluorination, and they show very different conformational behaviour and physical properties.

引用

页码：3105 / 3108

页数：4

共 11 条

[1] Contribution to the study of the Gauche effect. The complete structure of the anti rotamer of 1,2-difluoroethane [J].

Craig, NC ;

Chen, A ;

Suh, KH ;

Klee, S ;

Mellau, GC ;

Winnewisser, BP ;

Winnewisser, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) :4789-4790

[2]

Frisch M.J., 2004, Gaussian 03

[3]

Revision C.02

[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] FLEXIBLE MOLECULES WITH DEFINED SHAPE - CONFORMATIONAL DESIGN [J].

HOFFMANN, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (09) :1124-1134

[6] Synthesis and conformation of multi-vicinal fluoroalkane diastereoisomers [J].

Hunter, Luke ;

Slawin, Alexandra M. Z. ;

Kirsch, Peer ;

O'Hagan, David .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (41) :7887-7890

[7] Enantioselective synthesis of an all-syn four vicinal fluorine motif [J].

Hunter, Luke ;

O'Hagan, David ;

Slawin, Alexandra M. Z. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) :16422-16423

[8]

Ihrig A. M., 1970, Journal of the American Chemical Society, V92, P759, DOI 10.1021/ja00707a003

[9] α,β,γ-Trifluoroalkanes:: A stereoselective synthesis placing three vicinal fluorines along a hydrocarbon chain [J].

Nicoletti, M ;

O'Hagan, D ;

Slawin, AMZ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) :482-483

[10] A new generalized Karplus-type equation relating vicinal proton-fluorine coupling constants to H-C-C-F torsion angles [J].

Thibaudeau, C ;

Plavec, J ;

Chattopadhyaya, J .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :4967-4984

← 1 2 →