With all tested guests and reagents, a high iteroselectivity in favor of the monofunctionalized product was observed after the three-step sequence (Table ). Remarkably, in the case of cadaverine and and), only the monofunctionalized products were observed with all three reagents (NMR yields > 93%) (see the Experimental Part). With the other diamines, very small signals resulting from the presence of the difunctionalized product were detected in the 1 H NMR spectra. The reduced iteroselectivity observed with the smallest diamine (putrescine, n = 4) is certainly due to the smaller affinity constant for this guest combined with a decrease in the reactivity of the free amine group stemming from a steric clash between the reagent and the host (vide supra). For the longest diamine (n = 8), traces of the 2:1 host-guest complex between Ox3 and the diammonium ion were observed at the protection step (Step 1), resulting in the presence of traces of free diamine in the sample. Accumulation of the functionalized product through a one-pot cyclic process. The recycling of the molecular container in a one-pot cyclic process was investigated with cadaverine, the diamine with which the best results in terms of iteroselectivity were observed.