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An expedient procedure for the oxidative cleavage of olefinic bonds with PhI(OAc)2, NMO, and catalytic OsO4.
K C Nicolaou, Vikrant A Adsool, Christopher R H Hale
Organic letters 2010 Apr 02
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PhI(OAc)(2) in the presence of OsO(4) (cat.) and 2,6-lutidine cleaves olefinic bonds to yield the corresponding carbonyl compounds, albeit, in some cases, with alpha-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO(4) (cat.), 2,6-lutidine, and PhI(OAc)(2).
Citation
K C Nicolaou, Vikrant A Adsool, Christopher R H Hale.
An expedient procedure for the oxidative cleavage of olefinic bonds with PhI(OAc)2, NMO, and catalytic OsO4.
Organic letters.
2010 Apr 02;12(7):1552-5
Mesh Tags
Acetates
Aldehydes
Alkenes
Catalysis
Cyclic N-Oxides
Iodobenzenes
Ketones
Molecular Structure
Morpholines
Osmium Tetroxide
Oxidation-Reduction
Stereoisomerism
Substances
Acetates
Aldehydes
Alkenes
Cyclic N-Oxides
Iodobenzenes
Ketones
Morpholines
phenyliodosodiacetate
4-methylmorpholine N-oxide
Osmium Tetroxide
PMID: 20192259
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