Abstract
New diazapolyoxa macrocyclic ditosylates with 17–28-membered rings were synthesized by the application of the RCM technique to suitable α,ω-dienes. These compounds were employed as neutral carriers in Li-selective electrodes. The electrodes exhibited nearly Nernstian responses with relatively high selectivity for lithium over other inorganic cations.
Highlights
Efficient synthetic approaches to macrocyclic heterocyclic compounds have recently been developed using the RCM methodology.[1]
In the present work we applied our previously developed reaction sequence,[2,3,4] using the RCM technique, for the macrocyclization step to prepare a number of macrocyclic diazacrown ditosylates with varying ring sizes, in order to investigate their behavior in Li ion-selective electrodes
Lithium ion-selective electrodes were based on amide group type ionophores.[9,10,11,12,13]
Summary
Efficient synthetic approaches to macrocyclic heterocyclic compounds have recently been developed using the RCM methodology.[1]. RCM conditions: Grubbs' catalyst I (1.5-5mol%), DCM, Reflux 2 h RCM of these dienes proceeded under mild condition using [1,2,3,4,5] mol% of Grubbs’ catalyst I in CH2Cl2 to give excellent yields of the corresponding macrocyclic products [3, 5] and 7 respectively as an E/Z mixture in a ratio determined from their 1H NMR spectra as shown in Table 1 (cf Experimental section for E and Z isomer assignments).
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