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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