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Bicyclo[2.2.2]octene‐Based Molecular Tweezers and Cyclophanes
Author(s) -
Chou TehChang,
Liao KungChing,
Hwa ChingLun,
Tseng JuiChang
Publication year - 2012
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201100644
Subject(s) - chemistry , cyclophane , molecular tweezers , benzoic acid , carboxylate , molecule , hydroxybenzoate , diol , yield (engineering) , inclusion compound , stereochemistry , alkylation , tweezers , crystallography , polymer chemistry , organic chemistry , supramolecular chemistry , catalysis , materials science , metallurgy
The U‐shaped, tetraetheno‐bridged dicyclopenta[ b , i ]anthracenediol 1 was utilized as a platform molecule to construct molecular tweezers via bis‐esterification with benzoic acid and 9‐fluorenone‐2‐carboxylic acid using Yamaguchi protocol, affording the respective bis‐benzoate 3 (96%) and bis‐9‐fluorenone‐2‐carboxylate 6 in 59% yield. The latter bis‐esterification was accompanied by producing a mixed diester 7 (30%) and bis‐2,4,6‐trichlorobenzoate 8 (8%). Via bis‐ O ‐alkylation of diol 1 with ortho ‐, meta ‐, or para ‐α,α′‐dibromoxylene, the corresponding cyclophanes formed by the modes of [1+1] and [2+2] were obtained. Single‐crystal X‐ray structures of molecular tweezers 3 , 6 , 7 , [1+1]cyclophanes 11‐ m and 11‐ p , and [2+2]cyclophane 12‐ o were obtained and described.