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ADMET Polymerization of Amino‐Acid‐Based Diene
Author(s) -
Führer Felix N.,
Schlaad Helmut
Publication year - 2014
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201400166
Subject(s) - chemistry , polymer chemistry , polymerization , isomerization , diketopiperazines , ethylene glycol , molar mass , copolymer , catalysis , diene , polymer , organic chemistry , natural rubber
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‐ d i(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.