Polymer and Materials Science
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
The four 1,3-di(cyano and/or carbomethoxy)-substituted butadienes were synthesized. Their cyclopentadiene adduct precursors and, in one case, an anthracene adduct precursor were synthesized and pyrolyzed at 400-600°C (0.1-1.0 mm) to yield the four new dienes. Two crystalline precursors gave crystalline dienes 1,3-dicyano-1,3-butadiene, mp 79°C, and 1-carbomethoxy-3-cyanobutadiene, mp 45-46°C, in modest yields in small-scale experiments, which were completely characterized by elemental analyses and spectra. The other two liquid precursors produced no isolable or detectable dienes but led directly to polymer. The two crystalline dienes were exceptionally reactive, polymerizing on storage or when deliberately initiated with AIBN, but were moderately stable in solution. All polymers possessed the trans-1,4-structure exclusively. Because of the favorable location of the electronegative substituents for stabilizing the growing radical, these new dienes are the most reactive di-electronegatively substituted butadienes described.
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