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Stereoselective hydrogenation of lignin degradation model compounds

TitleStereoselective hydrogenation of lignin degradation model compounds
Publication TypeJournal Article
Year of Publication1997
AuthorsHu, TQ, James, BR, Rettig, SJ, Lee, CL
JournalCanadian Journal of Chemistry-Revue Canadienne De Chimie
Volume75
Pagination1234-1239
Date PublishedSep
Type of ArticleArticle
ISBN Number0008-4042
Keywordscatalytic hydrogenation, CATALYTIC-HYDROGENATION, COMPOUNDS, diastereomer, lignin degradation model, STEREOSELECTIVE, X-ray crystal structure
Abstract

Di-mu-chloro-bis(eta(4)-1,5-hexadiene)dirhodium(I) in a two-phase hexane-aqueous medium catalyzes the diastereoselective H-2-hydrogenation of lignin degradation model compounds 4-propylphenol, 2-methoxy-3-propylphenol, and 2,6-dimethoxy-3-propylphenol. The all-cis diastereomer is obtained selectively when the phenolic hydroxy group is protected as a methyl ether or when a model compound possessing two methoxy substituents adjacent to the phenolic hydroxy group is used. The relative stereochemistries of the hydrogenated products are established by X-ray crystal structure analysis and (or) H-1 NMR.

URL<Go to ISI>://A1997YE06300011