
TY  - JOUR
A1  - Atkinson, Ian M. 
A1  - Boghai, Davar M. 
A1  - Lindoy, Leonard F. 
A1  - Ghanbari, Bahram 
A1  - Meehan, George V. 
A1  - Saini, Vinod 
T1  - New Macrocyclic Ligands. VIII Di- and Tri-linked Macrocyclic Systems Incorporating N<emph tye="8">2</emph>O<emph tye="8">2</emph>-Donor Atoms
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1999
VL  - 52
IS  - 5
SP  - 351
EP  - 358
KW  - 
UR  - https://doi.org/10.1071/CH99054 
N2  - The synthesis and characterization of new lipophilic di- and tri-linked O2N2-donor macrocycles is reported. The synthesis of the dilinked species involved the initial alkylation of one secondary nitrogen of the parent 15-membered, O2N2-donor macrocycle (1) with 2-bromoethanol or with ethylene oxide to yield (2), followed by protection of the appended alcohol group by reaction with t-butyldiphenylsilyl chloride to give (3). Two such moieties were then bridged via a diacylation reaction with ClCO(CH2)8COCl to yield the corresponding diamide product (4). Deprotection of the alcohol functions followed by reduction of the both amide linkages resulted in formation of theN,N&#8242;-alkyl-linked species (5) incorporating two pendant hydroxyethyl groups. This product was then converted &#91;via the corresponding dichloro derivative (6)&#93; into the diether (7) by condensation with 4-t-butylphenol. By use of analogous chemistry, the trilinked trismacrocycle species (12), based on a phloroglucinol core, has also been synthesized. An aim of the present study was thus the preparation of new &#8216;linked&#8217; macrocyclic systems that might be expected to show higher lipophilicity than their corresponding single-ring systems. These were designed for future use as ionophores in metal ion membrane transport (and solvent extraction) experiments. 
ER  -

