Corey–Kim oxidation
E466667
Corey–Kim oxidation is an organic chemistry reaction that converts primary and secondary alcohols into aldehydes and ketones using N-chlorosuccinimide and dimethyl sulfide under mild conditions.
Statements (45)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction in organic chemistry
ⓘ
organic redox reaction ⓘ |
| advantage |
does not require heavy metals
ⓘ
operates under non-aqueous conditions ⓘ tolerates acid-sensitive functional groups ⓘ |
| avoidsOveroxidationTo | carboxylic acids ⓘ |
| byproduct |
dimethyl sulfide oxide (DMSO)
ⓘ
succinimide ⓘ |
| converts |
primary alcohols to aldehydes
ⓘ
secondary alcohols to ketones ⓘ |
| field | organic chemistry ⓘ |
| limitation | dimethyl sulfide has strong odor and toxicity concerns ⓘ |
| mechanismFeature |
activation of alcohol as alkoxysulfonium salt
ⓘ
beta-elimination to form carbonyl compound ⓘ formation of dimethylchlorosulfonium intermediate ⓘ |
| namedAfter |
Choung Un Kim
NERFINISHED
ⓘ
Elias James Corey NERFINISHED ⓘ |
| oxidantComponent | N-chlorosuccinimide NERFINISHED ⓘ |
| product |
aldehydes
ⓘ
ketones ⓘ |
| publishedIn | Tetrahedron Letters NERFINISHED ⓘ |
| reactionCondition |
mild conditions
ⓘ
typically low temperature ⓘ |
| reactionMedium | typically anhydrous conditions ⓘ |
| reactionType | oxidation of alcohols ⓘ |
| relatedTo |
PCC oxidation
NERFINISHED
ⓘ
Swern oxidation NERFINISHED ⓘ |
| safetyConcern |
N-chlorosuccinimide is an oxidizing agent
ⓘ
requires handling of malodorous dimethyl sulfide ⓘ |
| selectivity |
chemoselective for alcohol oxidation
ⓘ
generally stops at aldehyde stage for primary alcohols ⓘ |
| stoichiometry |
uses stoichiometric N-chlorosuccinimide
ⓘ
uses stoichiometric dimethyl sulfide ⓘ |
| substrate |
primary alcohols
ⓘ
secondary alcohols ⓘ |
| sulfurComponent | dimethyl sulfide ⓘ |
| typicalPhase | homogeneous solution phase ⓘ |
| typicalTemperatureRange | −20 °C to room temperature ⓘ |
| usedFor |
laboratory-scale synthesis of aldehydes
ⓘ
laboratory-scale synthesis of ketones ⓘ |
| usedIn | total synthesis of natural products ⓘ |
| usesReagent |
N-chlorosuccinimide
NERFINISHED
ⓘ
dimethyl sulfide ⓘ |
| usesSolvent | dichloromethane ⓘ |
| yearOfPublication | 1972 ⓘ |
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.