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A new route to the asymmetric cylindrical macrotricyclic ligands
Author(s) -
Krakowiak Krzysztof E.,
Bradshaw Jerald S.,
Kou Xiaolan,
Dalley N. Kent
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320343
Subject(s) - chemistry , bridge (graph theory) , solid state , crystallography , crown (dentistry) , stereochemistry , polymer chemistry , orthodontics , anatomy , medicine
New asymmeric cylindrical macrotricyclic ligands have been prepared containing two diaza‐12‐crown‐4 units connected by diethyleneoxy or triethyleneoxy and meta ‐ or para ‐xylylene bridges, 2‐4 . These materials were prepared in three steps by first treating 6‐tosyl‐6‐aza‐3,9‐dioxa‐1,11‐undecanediyl ditosylate with 3‐oxa‐1,5‐pentanediamine or 3,6‐dioxa‐1,8‐octanediamine to form ditosyl‐substituted bis(diaza‐12‐crown‐4)s connected by a diethyleneoxy or triethylencoxy bridge. These latter compounds were detosylated and treated with either para ‐ or meta ‐α,α'‐dibromoxylene to give new asymmetric cylindrical macrotricycles 2‐4 . The solid state structure of one of these ligands, 3 , has been determined by X‐ray diffraction methods.