Oxidative addition of py(dmgH)2Co-Na+ to a ribofuranosyl bromide: An unusual reaction with the cobaloxime ligand

Rachel M. Slade; Bruce P. Branchaud

doi:10.1021/om950795w

Oxidative addition of py(dmgH)₂Co^-Na⁺ to a ribofuranosyl bromide: An unusual reaction with the cobaloxime ligand

Rachel M. Slade, Bruce P. Branchaud

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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 language	English (US)
Pages (from-to)	2585-2587
Number of pages	3
Journal	Organometallics
Volume	15
Issue number	11
DOIs	https://doi.org/10.1021/om950795w
State	Published - May 28 1996
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Oxidative addition of py(dmgH)2Co-Na+ to a ribofuranosyl bromide: An unusual reaction with the cobaloxime ligand",

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.",

author = "Slade, {Rachel M.} and Branchaud, {Bruce P.}",

year = "1996",

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doi = "10.1021/om950795w",

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issn = "0276-7333",

publisher = "American Chemical Society",

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T1 - Oxidative addition of py(dmgH)2Co-Na+ to a ribofuranosyl bromide

T2 - An unusual reaction with the cobaloxime ligand

AU - Slade, Rachel M.

AU - Branchaud, Bruce P.

PY - 1996/5/28

Y1 - 1996/5/28

N2 - 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.

AB - 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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Oxidative addition of py(dmgH)₂Co^-Na⁺ to a ribofuranosyl bromide: An unusual reaction with the cobaloxime ligand

Abstract

ASJC Scopus subject areas

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