Oxidative addition of py(dmgH)2Co-Na+ to a ribofuranosyl bromide

An unusual reaction with the cobaloxime ligand

Rachel M. Slade, Bruce Branchaud

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Reaction of 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide (12) with NaCo(dmgH)2py (dmgH = dimethylglyoxime monoanion) in CH3CN was expected to proceed by normal oxidative addition to the carbon-bromine bond to form 2,3,5-tri-O-benzoyl ribofuranosyl cobaloxime (4) with a carbon-cobalt bond in place of the carbon-bromine bond. Instead, the major products, the isomeric (mixture of α- and β-anomers) dimethylglyoxime adducts 1-O-(dimethylglyoximato)-2,3,5-tri-O-benzoyl-D-ribofuranosides (17), were the result of reaction at the oxygen of the dimethylglyoxime ligand rather than at the cobalt.

Original languageEnglish (US)
Pages (from-to)2585-2587
Number of pages3
JournalOrganometallics
Volume15
Issue number11
StatePublished - May 28 1996
Externally publishedYes

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Bromides
bromides
Bromine
Carbon
bromine
Ligands
Cobalt
ligands
carbon
cobalt
adducts
Oxygen
oxygen
products
cobaloxime
dimethylglyoxime

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Oxidative addition of py(dmgH)2Co-Na+ to a ribofuranosyl bromide : An unusual reaction with the cobaloxime ligand. / Slade, Rachel M.; Branchaud, Bruce.

In: Organometallics, Vol. 15, No. 11, 28.05.1996, p. 2585-2587.

Research output: Contribution to journalArticle

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abstract = "Reaction of 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide (12) with NaCo(dmgH)2py (dmgH = dimethylglyoxime monoanion) in CH3CN was expected to proceed by normal oxidative addition to the carbon-bromine bond to form 2,3,5-tri-O-benzoyl ribofuranosyl cobaloxime (4) with a carbon-cobalt bond in place of the carbon-bromine bond. Instead, the major products, the isomeric (mixture of α- and β-anomers) dimethylglyoxime adducts 1-O-(dimethylglyoximato)-2,3,5-tri-O-benzoyl-D-ribofuranosides (17), were the result of reaction at the oxygen of the dimethylglyoxime ligand rather than at the cobalt.",
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