Sodium methylsulfinylmethylide
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| Abbreviations | NaDMSO |
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| Template:Longitem | Template:Chem2 |
| Molar mass | Template:Chem molar mass |
| Appearance | White solid, solution in DMSO is green |
| Solubility | Very soluble in DMSO and many polar organic solvents |
| Template:Longitem | Dimethyloxosulfonium methylide, Dimethyl sulfoxide |
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Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of dimethyl sulfoxide. It has the chemical formula Template:Chem2. This unusual salt has some uses in organic chemistry as a base and nucleophile.
Since the first publication in 1965 by Corey et al.,[1] a number of additional uses for this reagent have been identified.[2]
Preparation
Sodium methylsulfinylmethylide is prepared by heating sodium hydride[3] or sodium amide[4] in DMSO[5]
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.[6] NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide.[1][7]
Reaction with esters
NaDMSO condenses with esters (1) to form β-ketosulfoxides (2), which can be useful intermediates.[8] Reduction of β-ketosulfoxides with aluminium amalgam gives methyl ketones (3).[9] 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).[10]
References
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- ↑ a b Script error: No such module "Citation/CS1".
- ↑ Mukulesh Mondal "Sodium methylsulfinylmethylide: A versatile reagent" Synlett 2005, vol. 17, 2697-2698. Script error: No such module "CS1 identifiers".
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External links
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