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]

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Summary

Introduction

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).

Results
Conclusion

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