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Sodium methylsulfinylmethylide
Chemical compound From Wikipedia, the free encyclopedia
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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)CH−2Na+. This unusual salt has some uses in organic chemistry as a base and nucleophile.
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]
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
External links
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