Glaser Coupling of 4-Ethynyl[2.2]paracyclophane: The Formation of Two Diastereomers

被引：4

作者：

Hopf, Henning ^{[1
]}

Dix, Ina ^{[1
]}

Raev, Vitaly ^{[1
]}

Ernst, Ludger ^{[2
]}

机构：

[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany

[2] Tech Univ Carolo Wilhelmina Braunschweig, NMR Lab Chem Inst, D-38106 Braunschweig, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 08期

关键词：

Cyclophanes; Alkynes; Cross coupling; Structure elucidation; Chirality; NMR spectroscopy;

D O I：

10.1002/ejoc.201101495

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Glaser coupling of 4-ethynyl[2.2]paracyclophane (1) led to a mixture of dimers that could not be separated by either chromatographic or chemical methods. That two diasteromers of the dimer 2 were produced in a 7:3 ratio was demonstrated by the resolving power of modern NMR spectroscopy.

引用

页码：1653 / 1655

页数：3

共 9 条

[1] [2.2]paracyclophane/dehydroannulene hybrids: probing the aromaticity of the dehydro[14]annulene framework [J].

Hinrichs, H ;

Fischer, AK ;

Jones, PG ;

Hopf, H ;

Haley, MM .

ORGANIC LETTERS, 2005, 7 (17) :3793-3795

[2] Phane properties of [2.2]paracyclophane/dehydrobenzoannulene hybrids [J].

Hinrichs, Heino ;

Boydston, Andrew J. ;

Jones, Peter G. ;

Hess, Kirsten ;

Herges, Rainer ;

Haley, Michael M. ;

Hopf, Henning .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (27) :7103-7115

[3]

Hopf H., 2004, SYNTHESIS-STUTTGART, P2751, DOI DOI 10.1055/S-2004-834872

[4]

Hopf H., 2008, Angew. Chem, V120, P9954, DOI DOI 10.1002/ANGE.200800969

[5]

Hopf H., 2007, ACTA CRYSTALLOGR C, V63, P0468

[6] Ethynyl[2.2]paracyclophanes as building blocks for extended π-systems [J].

Hopf, Henning ;

Dix, Ina .

SYNLETT, 2006, (09) :1416-1418

[7] [2.2]Paracyclophanes in Polymer Chemistry and Materials Science [J].

Hopf, Henning .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) :9808-9812

[8] NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY . EFFECTS OF MOLECULAR ASYMMETRY ON CARBON-13 CHEMICAL SHIFTS [J].

KROSCHWITZ, JI ;

WINOKUR, M ;

REICH, HJ ;

ROBERTS, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (21) :5927-+

[9] Bridged bioxepines and bi[10]paracyclophanes - synthesis and absolute configuration of a bi[10]paracyclophane with two chiral planes and one chiral axis [J].

Tochtermann, W ;

Kuckling, D ;

Meints, C ;

Kraus, J ;

Bringmann, G .

TETRAHEDRON, 2003, 59 (39) :7791-7801

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