Synthesis and characterization of di- and tri-oxacalix[4]arenes

Michael Feldman, Colby College

Document Type Honors Thesis (Open Access)


Calixarenes are subset of macrocyclic ring systems in which all of the arenes composing the macrocycle are meta-linked. These compounds have been useful in guesthost binding studies, as well as in other areas of chemistry, and as such there has been a great deal of interest in these systems over the past 3 decades. While "annelated" carbon bridged calixarenes have been synthesized where each joined calixarene shares two rings, no one prior to now had reported the synthesis calixarenes sharing only one arene. Using a "component assembly" approach, combined with SNAr reactions, di-and trioxacalix[4]arenes have been synthesized. These structures have been characterized by 'H NMR and X-ray Crystallography as well by other methods.