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Step growth polymerization via tandem ene and diels‐alder reactions
Author(s) -
Mallakpour Shadpour E.,
Kolshorn Heinz,
Schollmeyer Dieter,
Stadler Reimund
Publication year - 1997
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.1997.021980203
Subject(s) - ene reaction , aromatization , regioselectivity , diels–alder reaction , chemistry , polymer chemistry , polymerization , polymer , intramolecular force , solvent , tandem , reaction mechanism , organic chemistry , materials science , catalysis , composite material
In contrast to other electron deficient enophiles or dienophiles which react with 1,4‐cyclohexadiene (1,4‐CHD) under aromatization, 1,2,4‐triazoline‐3,5‐diones react in a defined reaction sequence. In a first step the 1,4‐cyclohexadiene reacts via an ene‐reaction. The intermediately formed substituted 1,3‐cyclohexadiene immediately reacts in a Diels‐Alder reaction. The regiochemistry of the Diels‐Alder reaction is controlled by the solvent polarity. This reaction sequence can be used to synthesize polymers. Low‐molarmass model compounds were synthesized to elucidate the stereochemistry of the polymers. By varying the bistriazolinedione, polymers with backbones of different rigidity are available.