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Shape‐Persistent Chiral Alleno‐Acetylenic Macrocycles and Cyclophanes by Acetylenic Scaffolding with 1,3‐Diethynylallenes
Author(s) -
Odermatt Severin,
AlonsoGómez J. Lorenzo,
Seiler Paul,
Cid M. Magdalena,
Diederich François
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200501621
Subject(s) - cyclophane , chemistry , photoisomerization , intramolecular force , anthracene , stereochemistry , nuclear magnetic resonance spectroscopy , crystallography , photochemistry , isomerization , organic chemistry , crystal structure , catalysis
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 1 H NMR spectroscopy and X‐ray crystallography. The isolated stereoisomeric cyclophanes undergo photoisomerization; presumably the anthracene moieties serve as intramolecular sensitizers.