REACTIVE COMB-LIKE POLYMERS - KINETIC-STUDIES OF THE DIELS-ALDER REACTION OF FURAN-CONTAINING COMB-LIKE POLYMERS WITH DIMETHYL BUTYNEDIOATEBY MEANS OF H-1-NMR SPECTROSCOPY

The syntheses of some novel furan-containing monomers, N-[omega-(furfu rylcarbamoyl)alkyl]methacrylamide (2) and N-furfurylmethacrylamide (3) , and their corresponding polymers are described. Time-conversion meas urements of their Diels-Alder reactions with dimethyl butynedioate by means of H-1 NMR spectroscopy showed a deviation from pseudo-first-ord er kinetics. The influence of spacer length on the reaction velocity i s explained by steric hindrance and neighboring group effects. No devi ations from pseudo-first-order kinetics were observed during the Diels -Alder reaction of the low-molecular-weight model compounds N-[omega-( furfurylcarbamoyl)alkyl]isobutyramide (8) and N-furfurylisobutylamide (9) under the same reaction conditions.