N-chlorosuccinimide (NCS), dimethylsulfide (DMS) and triethylamine (TEA) are used to efficiently convert 1° or 2° alcohols into aldehydes and ketones respectively. First, NCS and DMS react to form the Corey-Kim reagent or S,S-dimethylsuccinimidosulfonium chloride, via dimethylsulfonium chloride. The nucleophilic 1° or 2° alcohol then attacks the Corey-Kim reagent, resulting in an alkoxysulfonium salt, which is deprotonated by TEA to form the desired carbonyl compound. Regenerated DMS is readily removed from the reaction mixture in vacuo.

• Reagents: NCS, DMS, TEA, Solvent (Toluene or CH₂Cl₂)
• Reactant: 1° or 2° Alcohol
• Product: Aldehyde or Ketone
• Type of Reaction: Oxidation

Mechanism

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Related Compounds