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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

journal contribution
posted on 2001-01-01, 00:00 authored by R Warrener, D Margetic, P Foley, D Butler, A Winling, K Beales, R Russell
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.

History

Journal

Tetrahedron

Volume

57

Issue

3

Pagination

571 - 582

Publisher

Pergamon

Location

Kidlington, England

ISSN

0040-4020

eISSN

1464-5416

Language

eng

Publication classification

C1 Refereed article in a scholarly journal