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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
- New Odorless Protocols for the Swern and Corey–Kim Oxidations. Tetrahedron Letters 2002, 43 (29), 5177-5179.
- New Odorless Method for the Corey–Kim and Swern Oxidations Utilizing Dodecyl Methyl Sulfide (Dod-S-Me). Tetrahedron 2003, 59 (42), 8393–8398.
- Dess-Martin Oxidation
- Jones Oxidation
- Swern Oxidation
- NCS (CAS 128-09-6)
- DMS (CAS 75-18-3)
- Triethylamine (CAS 121-44-8)