Abstract
AbstractPolymerizations of 3,4‐dihydro‐2H‐pyran‐2‐carboxyaldehyde (acrolein dimer) were investigated under several conditions. Polyacrolein dimer obtained at room temperature was found to have structural units (III) of 6,8‐dioxabicyclo[3,2,1] octane produced by an intraintermolecular reaction, in addition to the ordinary structures (I) produced by the unsaturated ether‐group polymerization and those (II) produced by the aldehyde‐group polymerization. The lower the polymerization temperature, the higher the selectivity of (II). The stronger the acidic character of initiators, the higher the selectivity of (I) and (III). With anionic catalysts, such as Al(C2H5)3 and dibenzene chromium, acrolein dimer gave a polymer containing only recurring structural units (II) at −78°C., while it did not give any polymer above –20°C. There consequently seems to be a ceiling temperature in the polymerization with anionic catalysts. The solubility of the polymers increased with increasing amounts of the bicyclic structure (III).
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