Sodium methylsulfinylmethylide
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| Preferred IUPAC name
Sodium (methanesulfinyl)methanide | |
| Other names
sodium dimsylate, dimsylsodium, NaDMSYL | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | NaDMSO |
| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| CH3S(O)CH2Na | |
| Molar mass | 100.11 g·mol−1 |
| 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 |
May form corrosive NaOH, May be explosive in certain circumstances.[1] |
| Related compounds | |
Related compounds |
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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Since the first publication in 1965 by Corey et al.,[2] a number of additional uses for this reagent have been identified.[3]
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]
