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Template‐Directed Synthesis of Helical Phenanthroline Cyclophanes
Author(s) -
Heuft Matthew A.,
Fallis Alex G.
Publication year - 2002
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 - 10.1002/1521-3773(20021202)41:23<4520::aid-anie4520>3.0.co;2-j
Subject(s) - isomerization , cyclophane , copper , chemistry , phenanthroline , stereochemistry , crystallography , organic chemistry , catalysis , crystal structure
A helical home for copper : A sequential, in situ desilylation/dimerization/decomplexation protocol has been used to generate helical enyne‐bridged heterocycles in a copper( I ) templated synthesis. Variable temperature 13 C NMR analysis of the copper complex (see calculated structure) indicated the barrier to helical isomerization was 13.6 kcal mol −1 , an increase of about 4 kcal mol −1 relative to the uncomplexed cyclophane.