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Improved Procedure for the Oxidative Cleavage of Olefins by OsO<sub>4</sub>−NaIO<sub>4</sub>

Organic Letters · 2004 · Vol. 6(19) · pp. 3217–3219
Wensheng YuYan MeiYing KangZhengmao HuaZhendong Jin

Abstract

[reaction: see text] Oxidative cleavage of olefins by OsO(4)-NaIO(4) sometimes suffers from low yields due to the formation of side products. It is found that the addition of 2,6-lutidine can suppress the side reactions and dramatically improve the yield of this classic reaction.

Oxidative Organic Chemistry ReactionsChemical Synthesis and ReactionsCatalytic C–H Functionalization MethodsChemistryOxidative cleavageYield (engineering)Oxidative phosphorylationCleavage (geology)Reaction conditionsMedicinal chemistryStereochemistryPhotochemistryOrganic chemistry

MeSH terms

AldehydesAlkenesCatalysisChemistry, OrganicIodatesOxidation-ReductionPyridinesMolecular StructureOsmium Compounds
Citations
428
FWCI
8.21
field-weighted impact
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6
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98%
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References
Notes - Osmium Tetroxide-Catalyzed Periodate Oxidation of Olefinic Bonds
The Journal of Organic Chemistry · 1956 · 661 citations
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Improved Procedure for the Oxidative Cleavage of Olefins by OsO<sub>4</sub>−NaIO<sub>4</sub> · Scinovex