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Step growth polymerization via tandem ene and diels-alder reactions

✍ Scribed by Shadpour E. Mallakpour; Heinz Kolshorn; Dieter Schollmeyer; Reimund Stadler


Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
629 KB
Volume
198
Category
Article
ISSN
1022-1352

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✦ Synopsis


Abstract

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.


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