Thermal and photochemical epimerization/equilibration of carbohydrate cobaloximes

G. X. Yu, D. R. Tyler, B. P. Branchaud

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

Epimeric carbohydrate alkyl cobaloximes 4:5, 9:10, and 12:13 can be equilibrated thermally or photochemically. In each case, one isomer is strongly favored: exo-3-deoxy-3-pyridyldimethylgly-oximatocobalt-1, 2:5,6-di-O-isopropylidene-α-D-glucofuranose 4 for the 4:5 epimer pair, exo-3-deoxy-3-pyridyldimethylglyoximatocobalt-5-O-carboxymethyl-1, 2-O-isopropylidene-α-D-xylofuranose 9 for the 9:10 epimer pair, and equatorial 1-deoxy-1-pyridyldimethylglyoximatocobalt-2,3,4, 6-tetra-O-benzyl-β-D-glucopyranose 12 for the 12:13 epimer pair. These data indicate that there is a strong facial preference for the coupling of py(dmgH)2Co· radicals with alkyl R· free radicals, with the preferred kinetic path leading to the more stable product.

Original languageEnglish (US)
Pages (from-to)5687-5691
Number of pages5
JournalJournal of Organic Chemistry
Volume66
Issue number17
DOIs
StatePublished - Aug 24 2001

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Thermal and photochemical epimerization/equilibration of carbohydrate cobaloximes'. Together they form a unique fingerprint.

  • Cite this