Synthesis and Hydrolysis Behavior of Side-Chain Functionalized Norbornenes

Autor:	Marcus Weck, Joseph R. Carlise, William S. Rees, Robert M. Kriegel
Rok vydání:	2005
Předmět:	chemistry.chemical_compound Hydrolysis Aqueous solution Monomer Polymerization chemistry Organic Chemistry Polymer chemistry Acetal Side chain Organic chemistry Nuclear magnetic resonance spectroscopy ROMP
Zdroj:	The Journal of Organic Chemistry. 70:5550-5560
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo050556a
Popis:	[reaction: see text] 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 degrees 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. Beta-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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b6990e06e11191f8b55dc632568d73fa https://doi.org/10.1021/jo050556a Zobrazit plný text záznamu