Sodium methylsulfinylmethylide

 ( Reagents For Organic Chemistry ) 

Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of dimethyl sulfoxide. It has the chemical formula . This unusual salt has some uses in organic chemistry as a base and nucleophile.

Since the first publication in 1965 by Corey et al., a number of additional uses for this reagent have been identified.Mukulesh Mondal "Sodium methylsulfinylmethylide: A versatile reagent" Synlett 2005, vol. 17, 2697-2698.

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Preparation Sodium methylsulfinylmethylide is prepared by heating sodium hydride or sodium amide in DMSO

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Reactions

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As a base The p K_a of DMSO is 35, which leads NaDMSO to be a powerful Brønsted base. NaDMSO is used in the generation of phosphorus and sulfur . NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide.

Trost, B. M.; Melvin, L. S., Jr. (1975). 9780127010601, Academic Press. ISBN 9780127010601

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Reaction with esters

NaDMSO condenses with ( 1) to form β-ketosulfoxides ( 2), which can be useful intermediates. Reduction of β-ketosulfoxides with aluminium amalgam gives methyl ( 3). 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 alpha to a carbonyl ( 5).

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External links

Categories: Reagents For Organic Chemistry, Organosodium Compounds

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