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Abstract

Two necessary conditions have been proposed for the π-electron delocalization across four bonds in bis-quatemary bromides of enamino spiro-ketal-type compounds. Dynamic NMR data analysis of these compounds suggests that π-electron delocalization takes place if the first atom is nitrogen and the fourth atom is either nitrogen or oxygen [i.e., N+ [DOUBLE BOND] C — C [DOUBLE BOND]N (or O)]. The second condition is that the end atoms of the four-bond system should not be the terminal group.