Inter- and intra-molecular pathways in polyamine synthesis from diamines †

Abstract

Characterisation, largely through crystal structure determinations of their metal complexes, of the polyamine products of several reactions between (in all but one case) polyalcohol benzenesulfonates and 1,2- and 1,3-diamines, confirmed that intramolecular reaction pathways are important only in the 1,2-diamine reactions. Even under conditions where the amine reactants are in large excess, however, it is possible to obtain products resulting from alkylation of a diamine by more than one molecule of sulfonate (or, in one case, of a bromochloroalkane). In metal ion complexes formed by the new ligands there are examples of only partial coordination of the N-donor sites, giving species which might be suitable for further, selective functionalisation at the unbound centres. Conversion of the complexes into macrocyclic derivatives also suited to further functionalisation is straightforward.