Shape-Persistent Chiral Alleno-Acetylenic Macrocycles and Cyclophanes by Acetylenic Scaffolding with 1,3-Diethynylallenes

Rings on her fingers: The chiral alleno‐acetylenic macrocycle 1 and the related cyclophane 2 with intriguing three‐dimensional shapes were prepared and isolated in diastereoisomerically pure form. The symmetries and structures of these novel unsaturated hydrocarbons were elucidated by 1H NMR spectro...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-08, Vol.44 (32), p.5074-5078
Main Authors: Odermatt, Severin, Alonso-Gómez, J. Lorenzo, Seiler, Paul, Cid, M. Magdalena, Diederich, François
Format: Article
Language:English
Subjects:
Acetylene - chemical synthesis
Acetylene - chemistry
Alkadienes - chemical synthesis
Alkadienes - chemistry
allenes
chirality
Chromatography, High Pressure Liquid
cross-coupling
macrocycles
Macrocyclic Compounds - chemical synthesis
Macrocyclic Compounds - chemistry
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
photoisomerization
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Rings on her fingers: The chiral alleno‐acetylenic macrocycle 1 and the related cyclophane 2 with intriguing three‐dimensional shapes were prepared and isolated in diastereoisomerically pure form. The symmetries and structures of these novel unsaturated hydrocarbons were elucidated by 1H NMR spectroscopy and X‐ray crystallography. The isolated stereoisomeric cyclophanes undergo photoisomerization; presumably the anthracene moieties serve as intramolecular sensitizers.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200501621