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Incorporation of a molecular hinge into molecular tweezers by using tandem gycloadditions onto 5,6-Dimenthylenenorbornene

journal contribution
posted on 2001-01-01, 00:00 authored by R Warrener, D Butler, L Liu, D Margetic, R Russell
Site-selective 1,3-dipolar coupling at the norbornene p-bond of 5,6-dimethylenenorbornene 1 yields cycloadducts with an end-fused 1,3-diene system which have been reacted with N=N (or C=C) dienophiles to produce ribbon molecules, in which the internal diazacyclohexene (or cyclohexene) subunits are capable of acting as conformational hinges. Direct coupling of 5,6-dimethylenenorbornene with 1,3,4-oxadiazoles or dual coupling with bis(cyclobutene epoxides) afforded bis(1,3-dienes) that diastereoselectively react with dienophiles to produce new, conformationally mobile, molecular tweezers.

History

Journal

Chemistry - a European journal

Volume

7

Issue

15

Pagination

3406 - 3414

Publisher

Wiley - V C H Verlag GmbH & Co. KGaA

Location

Weinheim, Germany

ISSN

0947-6539

eISSN

1521-3765

Language

eng

Publication classification

C1 Refereed article in a scholarly journal

Copyright notice

2001, Wiley

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