2,5-DIMETHOXY-1,4-BENZOQUINONE AND 2,5-DI-N-BUTOXY-1,4-BENZOQUINONE REACTIONS AND POLYMERIZATION WITH 1,6-HEXANEDIAMINE

The serendipitous formation of 2,5-dimethoxy-1,4-benzoquinone is reported from the reaction of 1,4-benzoquinone with methanol, DABCO, and paraformaldehyde. This monomer, and its di-n-butoxy analog, are also available from 2,5-dihydroxy-1,4-benzoquinone. These materials are capable of novel polycondensation reactions with diamines such as 1,6-hexanediamine. Use of m-cresol as polymerization solvent gave a dark, insoluble product while various amide solvents lead to orange or pink polymers that had average degrees of polymerization from 5 up to > 30. These polymers, plus model compounds obtained from 1-aminopropane and N,N'-dimethyl-1,6-hexanediamine, were characterized by FTIR, solution, and solid-state NMR.