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


Top Citations

Original Paper

Related Reactions

  • Dess-Martin Oxidation
  • Jones Oxidation
  • Swern Oxidation

Related Compounds

  • NCS (CAS 128-09-6)
  • Triethylamine (CAS 121-44-8)
  • Aldehyde
  • Ketone
By shuhan yang


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