SYNTHESIS OF A NOVEL MACROCYCLIC ARYLENE ETHER SULFONE

The present work reports the synthesis of a macrocyclic arylene ether sulfone, 4, in two steps. In the first step dichlorodiphenyl sulfone (1) was substituted with two Bisphenol A (2) moieties by a nucleophilic substitution reaction using three solvents and reagent systems: (a) potassium carbonate/dimethylacetamide, (b) sodium hydride/dimethylformamide, or (c) aqueous caustic/dimethyl sulfoxide. The product 3 was cyclized with dichlorodiphenyl sulfone to form 4 using the first and second procedures. For economy and convenience, the first system is the method of choice for this synthesis. The products were characterized by elemental analysis, solubility, IR, NMR, GPC, MS, TGA (in air and nitrogen atmospheres), and DSC.