For all of the NON-systems, conversion of TsCl is rapid (with the same yields being obtained after 15 min and longer reaction times), and the low yield of the product has been attributed to unwanted parallel tosylation reactivity involving the amide arms of the NON ligand. In the case of 6, the aryloxide X-donors of the TACN-supported ligand are markedly less nucleophilic, thereby suppressing side reactivity and enhancing fluoride delivery. Consistently, all of the reactions of 6 carried out with electrophiles containing a chloride leaving group generate the same Cacontaining product, identified as [{(t-BuTACN-Me)Ca}2(-Cl)] -. The 1 H NMR spectra obtained in situ for all of these reactions match that measured for a sample of [K(2.2.2-crypt)][{(t-BuTACN-Me)Ca}2(-Cl)] which was independently synthesized by reacting complex 4 with excess KCl and 2.2.2-cryptand at 80 °C (see Figure for details).