6533b7dcfe1ef96bd1271e28
RESEARCH PRODUCT
Step growth polymerization via tandem ene and diels-alder reactions
Heinz KolshornDieter SchollmeyerReimund StadlerShadpour Mallakpoursubject
Reaction mechanismPolymers and PlasticsChemistryOrganic ChemistryAromatizationRegioselectivityCondensed Matter PhysicsStep-growth polymerizationchemistry.chemical_compoundCascade reactionPolymer chemistryMaterials ChemistryPhysical and Theoretical ChemistrySolvent effectsImideEne reactiondescription
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-molar-mass model compounds were synthesized to elucidate the stereochemistry of the polymers. By varying the bistriazolinedione, polymers with backbones of different rigidity are available.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1997-02-01 | Macromolecular Chemistry and Physics |