Reaction of the eneamine 1 formed in situ from isoquinoline and sodium triethylborohydride with aromatic dialdehydes 3 produces 4,4′‐coupled bis(isoquinolines) 4 in good yields. These compounds are readily oxidized with manganese dioxide to the corresponding diketones 5.

Reissert compounds are the result of the formal addition of acyl cyanides across the CH=N bonds of aromatic heterocyclic compounds or acyclic imines. The chemistry of this class of compounds is primarily based upon the acidity of the CH(CN)‐NCOR moiety and the nucleophilic reactivity of the conjugate base. Three methodologies for application of this chemistry to the synthesis of polymers are summarized: 1) formation of polyamides by the “Reissert reaction” of suitable difunctional imines and diacid chlorides, 2) condensation of the anions of difunctional Reissert compounds with dielectrophiles such as dihaloalkanes and dialdehydes and 3) use of Reissert compound chemistry to construct novel monomers for use in traditional condensation polymerizations. All three methodologies are proven to be effective in the production of nitrogen containing polymers.

An AA bisphenolic monomer (13), an AB activated fluoro‐phenolic monomer (14), and an AB2 alcohol‐diester monomer precursor (17), all based on the isoquinoline nucleus, were prepared using Reissert compound chemistry. Additionally, model reactions established the efficiency of condensation of isoquinoline Reissert compounds with dihaloalkanes, providing evidence of the potential of this reaction to produce high molecular weight polymers, which was subsequently realized. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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