chemistry

Sodium methylsulfinylmethylide

Sodium methylsulfinylmethylide is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Sodium methylsulfinylmethylide rather than just read about it. In short: Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of dimethyl sulfoxide. It has the chemical formula CH3S(O)CH−2Na+.

Key takeaways

Sodium methylsulfinylmethylide belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Sodium methylsulfinylmethylide to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Sodium methylsulfinylmethylide from memory before moving on to harder problems.

Reference excerpt

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. First reported by Corey and Chaykovsky in 1962. and subsequent usage in organic synthesis reported in 1965 by Corey et al., a number of additional uses for this reagent have been identified.

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

CH3S(O)CH3 + NaH → CH3S(O)CH−2Na+ + H2 CH3S(O)CH3 + NaNH2 → CH3S(O)CH−2Na+ + NH3

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. NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide.

Reaction with esters NaDMSO condenses with esters (1) to form β-ketosulfoxides (2), which can be useful 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). β-ketosulfoxides can also be used in the Pummerer rearrangement to introduce nucleophiles alpha to a carbonyl (5).

Methylation of sugars Permethylation of sugars with dimsyl sodium was reported by Hakomori in 1964 This usage is sometimes called Hakomori methylation.

References

External links "The Dimethyl Sulfoxide (DMSO) Anion — Dimsyl Ion" (PDF). Gaylord Chemical Corporation. October 2007. Archived from the original (PDF) on 2011-07-11. "Preparation of dimsyl sodium". June 2009.

Illustrations

Worked examples

Example 1 — a first encounter with Sodium methylsulfinylmethylide

Start with the simplest possible case. Write down what Sodium methylsulfinylmethylide claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Sodium methylsulfinylmethylide before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Sodium methylsulfinylmethylide ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Sodium methylsulfinylmethylide

In research: Sodium methylsulfinylmethylide appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Sodium methylsulfinylmethylide in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Sodium methylsulfinylmethylide is common in secondary-school and first-year university syllabi. It links to neighbouring topics Organosodium compounds, Reagents for organic chemistry, so understanding it makes those chapters shorter.
In everyday life: Look for Sodium methylsulfinylmethylide outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Sodium methylsulfinylmethylide in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Sodium methylsulfinylmethylide means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Sodium methylsulfinylmethylide out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Sodium methylsulfinylmethylide in simple terms?

Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of dimethyl sulfoxide. It has the chemical formula CH3S(O)CH−2Na+.

Why does Sodium methylsulfinylmethylide matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Sodium methylsulfinylmethylide?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Sodium methylsulfinylmethylide.