We report herein a 1,3-difunctionalization of cyclopropylamines that serve as a π nucleophile in a two-electron (2e) SN2-like ring opening pathway. N-Iodosuccinimide (NIS) or in situ generated cyanogen iodide (ICN) is employed as electrophilic iodinating reagents in conjunction with TMSCN or succinimide to furnish multiple pairs of functional groups disposed in a 1,3-manner. This 2e ring opening manifold overcomes the constraint of our previously reported 1e protocol as demonstrated by successful activation of monocyclic tertiary cyclopropylamines.