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Polymerization of Enantiomerically Pure exo ‐ N ‐(Norborn‐2‐ene‐5‐carboxyl)‐ L ‐phenylalanine Ethyl Ester and endo , endo ‐ N , N ‐(Norborn‐5‐ene‐2,3‐dicarbimido)‐ L ‐valine Ethyl Ester Using Novel Ruthenium 1,3‐Dimesityl‐3,4,5,6‐tetrahydropyrimidin‐2‐ylidenes
Author(s) -
Wang Dongren,
Yang Liangru,
Decker Ulrich,
Findeisen Matthias,
Buchmeiser Michael R.
Publication year - 2005
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200500578
Subject(s) - polymerization , monomer , pyridine , ene reaction , chemistry , catalysis , polymer chemistry , ruthenium , stereochemistry , polymer , medicinal chemistry , organic chemistry
Summary: The polymerization of two chiral, enantiomerically pure monomers, i.e., exo ‐ N ‐(norborn‐2‐ene‐5‐carboxyl)‐ L ‐phenylalanine ethyl ester ( 1 ) and endo , endo ‐ N , N ‐(norborn‐5‐ene‐2,3‐dicarbimido)‐ L ‐valine ethyl ester ( 2 ) using the ruthenium‐based, 1,3‐dimesityl‐3,4,5,6‐tetrahydropyrimidin‐2‐ylidene (Mes 2 ‐THP)‐derived initiators RuCl 2 (Mes 2 ‐THP)(CH‐2‐(2‐PrO‐)‐5‐NO 2 C 6 H 3 ) ( 3 ) and RuCl 2 (Mes 2 ‐THP)(CHC 6 H 5 )(pyridine) ( 4 ), is described. Polymerization of 1 mediated by either 3 or 4 proceeded in a living manner with good control over molecular weight. The polymerization of 2 mediated by either 3 or 4 yielded a polymer with an exclusive all‐ trans structure.Structure of the RuCl 2 (Mes 2 ‐THP)(CHC 6 H 5 )(pyridine) ( 4 ) catalyst synthesized here.