Nitrodisplacement reactions and the synthesis of bis (ether anhydride) s from dihydroxynaphthalenes

Abstract

Nitrodisplacement reactions between all ten dihydroxynaphthalenes and 4-nitrophthalodinitrile have been studied. Apart from 1,8-dihydroxynaphthalene, all dihydroxynaphthalenes undergo nitrodisplacement but only 1,5-, 2,3-, 2,6- and 2,7-dihydroxynaphthalenes give high yields of pure bis(ether dinitrile). The bisfether dinitrile's produced in high yield were hydrolysed and converted to bis(ether anhydride) for subsequent synthesis of poly(ether imide)s. Success in nitrodisplacement correlates with high redox potentials for the dihydroxynaphthalenes, except for 1,8-dihydroxynaphthalene which probably fails to react because of steric constraints at the peri positions.