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Sodium methylsulfinylmethylide (also called NaDMSO) is the conjugate base of dimethyl sulfoxide. It has several uses in organic chemistry as a base and nucleophile.
Since the first publication in 1965 by Corey et al., a large number of publications have described additional uses for this reagent.
Additional recommended knowledge
Sodium methylsulfinylmethylide is prepared by heating sodium hydride or sodium amide in DMSO at 70 °C for 1 hr.
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. NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide.
As a Nucleophile
Reaction with esters
NaDMSO will condense with esters (1) to form β-ketosulfoxides (2), which have been shown to be very useful synthetic intermediates. Reduction of β-ketosulfoxides with aluminium amalgam gives methyl ketones (3). Reaction with alkyl halides followed by elimination gives α,β-unsaturated ketones (4). Interestingly, β-ketosulfoxides can also be used in the Pummerer rearrangement to introduce nucleophiles alpha to a carbonyl (5).
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Sodium_methylsulfinylmethylide". A list of authors is available in Wikipedia.|