Sodium methylsulfinylmethylide

Sodium methylsulfinylmethylide is the sodium salt of dimethyl sulfoxide. It has the chemical formula. This unusual salt has some uses in organic chemistry as a base and nucleophile.
Since the first publication in 1965 by Corey et al., a number of additional uses for this reagent have been identified.

Preparation

Sodium methylsulfinylmethylide is prepared by heating sodium hydride or sodium amide in DMSO

Reactions

As a base

The pK_a of DMSO is 35, which leads NaDMSO to be a powerful Brønsted base. NaDMSO is used in the generation of phosphorus and sulfur ylides. NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide.

Reaction with esters

NaDMSO condenses with esters to form β-ketosulfoxides, which can be useful intermediates. Reduction of β-ketosulfoxides with aluminium amalgam gives methyl ketones. Reaction with alkyl halides followed by elimination gives α,β-unsaturated ketones. β-ketosulfoxides can also be used in the Pummerer rearrangement to introduce nucleophiles alpha to a carbonyl.