Synthesis, structure, and host ability of macrocycles based on the structural diversity of 1,3-diene

Article abstract of DOI:10.1016/S0040-4039(00)02328-5

Macrocycles consisting of both a 1,3-diene unit and a polyether linkage were prepared by the reaction of muconic acid dichloride with diols containing a polyether linkage. The 1,3-diene moiety was complexed by iron carbonyl to furnish macrocycles bearing a (η⁴-diene)tricarbonyliron moiety. The structures of the macrocycles were determined by NMR and IR spectroscopy, and by X-ray structural analysis. The macrocycles formed complexes with some ammonium salts and their association constants varied according to whether the structure of the 1,3-diene moiety was complexed or uncomplexed. Ring-size effects of the macrocycles on the association constants were also studied.