M. Buchmeiser, F. Sinner, M. Mupa
2000
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95
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Journal
Macromolecules
Abstract
A series of norbornene-based, l-valine- and l-phenylalanine-containing chiral monomers have been prepared. Starting from norborn-2-ene-5-carboxylic acid chloride and norborn-2-ene-5,6-dicarboxylic anhydride, N-(norborn-2-ene-5-carboxyl)-l-valine (I), N-(norborn-2-ene-5-carboxyl)-l-phenylalanine (II), N-(norborn-2-ene-5-carboxyl)-l-phenylalanine ethyl ester (III), the N,N-(norborn-2-ene-5,6-dicarbimid) (NBDCI)-protected amino acid derivatives NBDCI-l-valine (IV), NBDCI-l-phenylalanine (V), NBDCI-l-valine-tert-butylamide (VI), NBDCI-l-valine-anilide (VII), NBDCI-l-valine-m-nitroanilide (VIII), and NBDCI-l-valine-p-chloroanilide (IX) have been synthesized. Compounds I−IX were polymerized via ring-opening metathesis polymerization (ROMP) using initiators based on both molybdenum (Mo(N-2,6-Me2-C6H3)(CHCMe2Ph)(OCMe(CF3)2)2) (1) and ruthenium (Cl2Ru(CHPh-p-F)(PCy3)2, Cy = cyclohexyl) (2). The polymers were characterized in terms of cis/trans structure as well as optical rotation. Bromomethylated, beaded polymer ...