2,2'-Bipyridine → Methyl Methacrylate/Butyl Acrylate Methyl Methacrylate

Participants

Reaction Conditions

Reaction Steps

To a 10 ml round bottom flask with a stir bar, 2,2′-bipyridine (32.8 mg, 0.21 mmol), copper (I) bromide (10.2 mg, 0.07 mmol), and α,α′-dibromo-p-xylene (18.5 mg, 0.07 mmol) were added. The flask was sealed with a rubber septum and the contents of the flask degassed by applying a vacuum and backfilling with argon. Degassed butyl acrylate (5.0 ml, 34.9 mmol) was added via syringe. The reaction mixture was heated at 100° C. and stirred. After eight hours the reaction was viscous. Conversion was found to be 93% by 1H NMR; Mn=60,500, Mw/Mn=1.3. The reaction was cooled to 50° C. and then placed under vacuum to remove residual butyl acrylate. After 1 hour, degassed methyl methacrylate (2.25 ml, 21 mmol) was added via syringe and the reaction heated to 100° C. After 12 h, the reaction was stopped. Conversion of the methyl methacrylate was 96%; Mn=93,600, Mw/Mn=1.5. The polymer was purified by dissolving in THF and passing over alumina, followed by repeated precipitation into methanol. 1H NMR showed that the polymer contained 32% methyl methacrylate.

Provenance & Evidence