Synthesis and hydrolysis behavior of side-chain functionalized norbornenes

Joseph R. Carlise, Robert M. Kriegel, William S. Rees, Marcus Weck

Research output: Contribution to journalArticle

Abstract

The stabilities of various functionalized norbornenes that are monomers for the ring-opening metathesis polymerization (ROMP) in aqueous solution were evaluated toward hydrolysis under a range of temperatures (37, 60, and 80 °C) and pH values (3-9). All monomers contain hydrolyzable linkages to pendant functional groups, and conclusions were drawn relating to how the chemical diversity of these pendant functional groups, in accordance with the pH and temperature variations, affect hydrolysis of the aforementioned linkages. The hydrolysis was monitored by reverse phase HPLC analysis, and/or NMR spectroscopy. As expected, monomers containing ester linkages were fairly labile at higher pH values, while acetal-based linkers were cleaved at lower pH values. β-Amino ester groups experienced a significant increase in hydrolysis rate, while carboxylic acid-containing monomers did not follow any clear trend. Saccharide-containing monomers exhibited unique behaviors for various pH values and temperature ranges.

Original languageEnglish (US)
Pages (from-to)5550-5560
Number of pages11
JournalJournal of Organic Chemistry
Volume70
Issue number14
DOIs
StatePublished - Jul 8 2005

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Hydrolysis
Monomers
Functional groups
Esters
Acetals
Ring opening polymerization
Carboxylic Acids
Temperature
Nuclear magnetic resonance spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and hydrolysis behavior of side-chain functionalized norbornenes. / Carlise, Joseph R.; Kriegel, Robert M.; Rees, William S.; Weck, Marcus.

In: Journal of Organic Chemistry, Vol. 70, No. 14, 08.07.2005, p. 5550-5560.

Research output: Contribution to journalArticle

Carlise, Joseph R. ; Kriegel, Robert M. ; Rees, William S. ; Weck, Marcus. / Synthesis and hydrolysis behavior of side-chain functionalized norbornenes. In: Journal of Organic Chemistry. 2005 ; Vol. 70, No. 14. pp. 5550-5560.
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