Article (Scientific journals)
Probing the stereoselectivity of the ruthenium-catalyzed ring-opening metathesis polymerization of norbornene and norbornadiene diesters
Delaude, Lionel; Demonceau, Albert; Noels, Alfred
2003In Macromolecules, 36 (5), p. 1446-1456
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Abstract :
[en] The ring-opening metathesis polymerization (ROMP) of two optically active 2,3-dicarboalkoxynorbornadienes derived from (S)-(-)-2-methyl-1-butanol and (R)-(-)-2-butanol were carried out in the presence of the [RuCl2(P-cymene)](2) catalyst precursor activated by trimethylsilyldiazomethane (TMSD). H-1 and C-13 NMR analyses showed that a high degree of stereoregularity was achieved, and homonuclear proton-proton COSY spectroscopy indicated that the major trans fractions of the polymers were most likely isotactic, while the minor cis fractions were syndiotactic. Ring-opened metathesis polymers were also made from 2,3-dicarbomethoxynorbornadiene and exo,exo-2,3-dicarbomethoxy-5-norbornene. They were hydrogenated into the corresponding polynorbornanes using diimide. The NMR spectra of the reduced materials confirmed that the unsaturated parent polymers had an all-trans highly isotactic microstructure. A tentative mechanism involving arene loss, carbene formation, and monomer chelation is proposed to account for the observed stereoselectivities.
Disciplines :
Chemistry
Author, co-author :
Delaude, Lionel  ;  Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique
Demonceau, Albert ;  Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique
Noels, Alfred ;  Université de Liège - ULiège > Services généraux (Faculté des sciences) > Relations académiques et scientifiques (Sciences)
Language :
English
Title :
Probing the stereoselectivity of the ruthenium-catalyzed ring-opening metathesis polymerization of norbornene and norbornadiene diesters
Publication date :
2003
Journal title :
Macromolecules
ISSN :
0024-9297
eISSN :
1520-5835
Publisher :
Amer Chemical Soc, Washington, United States - District of Columbia
Volume :
36
Issue :
5
Pages :
1446-1456
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
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