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The reaction of 3,4-dicyanopyridine or other phthalonitrile bearing electron withdrawing groups such as nitro or fluoro with DBU gives a reddish brown species at room temperature, which remains stable even on heating the reaction mixture for 24-48 h at 140 °C. This species is believed to be a DBU-phthalonitrile adduct and this adduct remains stable even on heating in the presence of metal salt such as zinc acetate and ionic liquid 1a. No such adduct formation was observed when 3,4-dicyanopyridine was added in the reaction mixture of ionic liquid 1b and DBU at 140 °C.
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