Odorless Corey-Kim

The first step of the mechanism of the Corey-Kim oxidation is the reaction of dimethylsulfide with A/-chlorosuccinimide to generate the electrophilic active species, S,S-dimethylsuccinimidosulfonium chloride Corey-Kim reagent) via dimethylsulfonium chloride. The sulfonium salt is then attacked by the nucleophilic alcohol to afford an alkoxysulfonium salt. This alkoxysulfonium salt is deprotonated by triethylamine and the desired carbonyl compound is formed. The dimethylsulfide is regenerated, and it is easily removed from the reaction mixture in vacuo. In the odorless Corey-Kim oxidation instead of dimethylsulfide, dodecylmethylsulfide is used. This sulfide lacks the unpleasant odor of DMS due to its low volatility. 

Nishide, K., Ohsugi, S.-i., Fudesaka, M., Kodama, S., Node, M. New odorless protocols for the Swern and Corey-Kim oxidations. Tetrahedron Lett. 2002, 43, 5177-5179. 

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