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Sodium methylsulfinylmethylide

Chemical compound From Wikipedia, the free encyclopedia

Sodium methylsulfinylmethylide
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Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of dimethyl sulfoxide. It has the chemical formula CH3S(O)CH2Na+. This unusual salt has some uses in organic chemistry as a base and nucleophile.

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Since the first publication in 1965 by Corey et al.,[2] a number of additional uses for this reagent have been identified.[3]

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Preparation

Sodium methylsulfinylmethylide is prepared by heating sodium hydride[4] or sodium amide[5] in DMSO[6]

CH3S(O)CH3 + NaH → CH3S(O)CH2Na+ + H2
CH3S(O)CH3 + NaNH2 → CH3S(O)CH2Na+ + NH3

Reactions

As a base

The pKa of DMSO is 35, which leads NaDMSO to be a powerful Brønsted base. NaDMSO is used in the generation of phosphorus and sulfur ylides.[7] NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide.[2][8]

Reaction with esters

NaDMSO condenses with esters (1) to form β-ketosulfoxides (2), which can be useful intermediates.[9] Reduction of β-ketosulfoxides with aluminium amalgam gives methyl ketones (3).[10] Reaction with alkyl halides followed by elimination gives α,β-unsaturated ketones (4). β-ketosulfoxides can also be used in the Pummerer rearrangement to introduce nucleophiles alpha to a carbonyl (5).[11]

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References

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