1,4‐Di(homo)allyl‐2,5‐diketopiperazines are synthesized and polymerized via ADMET using the Hoveyda–Grubbs 2nd generation catalyst. The but‐3‐enylated diketopiperazine can be converted into unsaturated tertiary polyamide with molar mass of <3000 g mol−1, whereas the allylated diketopiperazine cannot. Double‐bond isomerization occurs regardless of whether or not benzoquinone is present. A polyesteramide with a higher molar mass of ca. 4800 g mol−1 is obtained by the alternating copolymerization (ALTMET) of 1,4‐di(but‐3‐enyl)‐2,5‐diketopiperazine and ethylene glycol diacrylate. A post‐polymerization modification of the poly(ester)amides via radical thiol‐ene chemistry, however, fails.
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