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Incorporation of a Molecular Hinge into Molecular Tweezers by Using Tandem Cycloadditions onto 5,6‐Dimethylenenorbornene
Author(s) -
Warrener Ronald N.,
Butler Douglas N.,
Liu Ligong,
Margetic Davor,
Russell Richard A.
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010803)7:15<3406::aid-chem3406>3.0.co;2-m
Subject(s) - molecular tweezers , tandem , chemistry , hinge , norbornene , molecule , stereochemistry , crystallography , supramolecular chemistry , materials science , organic chemistry , polymerization , polymer , physics , classical mechanics , composite material
Abstract Site‐selective 1,3‐dipolar coupling at the norbornene π‐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.