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Synthesis and X‐ray Structure of Amide‐Based Macrocycles, Catenanes and Pretzelane
Author(s) -
Li Qian Yi,
Vogel Erik,
Parham Amir Hossain,
Nieger Martin,
Bolte Michael,
Fröhlich Roland,
Saarenketo Pauli,
Rissanen Kari,
Vögtle Fritz
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200111)2001:21<4041::aid-ejoc4041>3.0.co;2-7
Subject(s) - catenane , chemistry , isophthalic acid , amide , hydrogen bond , molecule , crystallography , crystal structure , yield (engineering) , xylylene , stereochemistry , solvent , polymer chemistry , organic chemistry , materials science , polyester , metallurgy , terephthalic acid
The syntheses and crystal structure studies of amide‐based catenanes derived from m ‐phenylene diacrylic acid and 5‐acetoxy isophthalic acid (17% and 3% yield of 4a and 4b resp.) and octalactam macrocycles (21% yield of 3 ) are described. Hydrogen bonding patterns play a key role in the formation of the different conformations of octalactam 3 . The crystal structures of 3 reveal a number of hydrogen‐bonding interactions between the macrocycle and two different solvent molecules, which are presumably responsible for the different conformations. Furthermore, we report the X‐ray structure of a catenane, which was converted into a “pretzelane” by bridging two phenolic hydroxy groups with a p ‐xylylene unit.