6533b839fe1ef96bd12a6e82

RESEARCH PRODUCT

Cyclodextrins in Polymer Synthesis: Enantiodiscrimination in Free-Radical Polymerization of Cyclodextrin-Complexed Racemic N -Methacryloyl-D,L -phenylalanine Methyl Ester

Helmut RitterDieter SchollmeyerSabine Schwarz-barac

subject

chemistry.chemical_classificationReaction mechanismPolymers and PlasticsCyclodextrinOrganic ChemistryRadical polymerizationtechnology industry and agricultureDiastereomerPolymerchemistry.chemical_compoundMonomerchemistryPolymerizationPolymer chemistrypolycyclic compoundsMaterials ChemistryProton NMR

description

The enantiodiscriminating polymerization of racemic cyclodextrin-complexed N-methacryloylphenylalanine methyl ester is investigated 1 H NMR spectra of the complexes with methylated β-cyclodextrin in D 2 O manifest splittings due to chiral recognition. The different stabilities of the diastereomeric complexes influence the kinetics of the homopolymerization, particularly at 0°C. An enrichment of the residual N-methacryloyl-L-phenylalanine methyl ester of 14% was achieved after 21 h of polymerization.

https://doi.org/10.1002/marc.200391325