Shape‐Persistent Chiral Alleno‐Acetylenic Macrocycles and Cyclophanes by Acetylenic Scaffolding with 1,3‐Diethynylallenes | Zendy

Odermatt Severin | Zendy; AlonsoGómez J. Lorenzo | Zendy; Seiler Paul | Zendy; Cid M. Magdalena | Zendy; Diederich François | Zendy

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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.

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