Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of the conjugate base of dimethyl sulfoxide. This unusual salt has some uses in organic chemistry as a base and nucleophile.
Names | |
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Preferred IUPAC name
Sodium (methanesulfinyl)methanide | |
Other names
sodium dimsylate, dimsylsodium, NaDMSYL
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Identifiers | |
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3D model (JSmol)
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Abbreviations | NaDMSO |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C2H5NaOS | |
Molar mass | 100.13 |
Appearance | White solid, solution in DMSO is green |
decomposes | |
Solubility | Very soluble in DMSO and many polar organic solvents |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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May form corrosive NaOH, May be explosive in certain circumstances.[1] |
Related compounds | |
Related compounds
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Dimethyloxosulfonium methylide, dimethyl sulfoxide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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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]
Sodium methylsulfinylmethylide is prepared by heating sodium hydride[4] or sodium amide[5] in DMSO[6]
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]
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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: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 6, p. 531.
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: CS1 maint: multiple names: authors list (link)