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The Synthesis Of New Maleimide Addition Polymer Precursors, Richard B. Brown

Chemistry & Biochemistry Theses & Dissertations

1H-2,3-dimethylpyrrolo(1,2-a) benzimidazol-l-one (27) and 1H,9H- 2,3,7,8-tetramethyl-bispyrrolo(1,2-a:6,7-a')benzodiimidazo1-1,9-dione (32) have been synthesized from dimethylmaleic anhydride and o-phenylenediamine and 1,2,4,5-tetraaminobenzene, respectively. The presence of reactive olefinic double bonds in the synthesized compounds was of interest as a site for possible addition polymerization.

The synthetic route involved, in both cases, a simple nucleophilic substitution reaction between the diamine(or tetraamine) and the anhydride to form an intermediate amide-acid-amine which rapidly cyclized to the imide amine. The final ring closure required more rigorous conditions and occurred at melt reaction temperatures.