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syn-Facial hetero-bridged [n]polynorbornanes : a new class of polarofacial framework molecules composed of fused 7-oxa- and 7-azanorbornanes

Warrener, Ronald N., Margetic, Davor, Foley, Patrick J., Butler, Douglas N., Winling, Alain, Beales, Kerry A. and Russell, Richard A. 2001, syn-Facial hetero-bridged [n]polynorbornanes : a new class of polarofacial framework molecules composed of fused 7-oxa- and 7-azanorbornanes, Tetrahedron, vol. 57, no. 3, pp. 571-582, doi: 10.1016/S0040-4020(00)01027-9.

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Title syn-Facial hetero-bridged [n]polynorbornanes : a new class of polarofacial framework molecules composed of fused 7-oxa- and 7-azanorbornanes
Author(s) Warrener, Ronald N.
Margetic, Davor
Foley, Patrick J.
Butler, Douglas N.
Winling, Alain
Beales, Kerry A.
Russell, Richard A.
Journal name Tetrahedron
Volume number 57
Issue number 3
Start page 571
End page 582
Total pages 8 p.
Publisher Pergamon
Place of publication Kidlington, England
Publication date 2001-01
ISSN 0040-4020
1464-5416
Summary New oxygen-bridged norbornane-fused cyclobutene epoxides and bis-(cyclobutene epoxides) are described and shown to react stereoselectively with 7-azanorbornenes to produce syn-facial N,O-bridged polynorbornanes and stereorandomly with 7-oxanorbornenes to produce O,O-bridged polynorbornanes as mixtures of syn-facial and anti-facial products.[1] Polarofacial systems containing up to six syn-facial norbornane bridges are described, while systems with seven co-facial oxygen atoms have been prepared by incorporating terminal epoxide rings to O5-[5]polynorbornanes. Ester-substituted 1,3,4-oxadiazoles are shown to be useful reagents for coupling 7-oxanorbornanes and produce predominantly syn-facial O-bridged polarofacial systems together with their anti-facial isomers.
Language eng
DOI 10.1016/S0040-4020(00)01027-9
Field of Research 030503 Organic Chemical Synthesis
HERDC Research category C1 Refereed article in a scholarly journal
Persistent URL http://hdl.handle.net/10536/DRO/DU:30008455

Document type: Journal Article
Collection: School of Biological and Chemical Sciences
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