chemistry

N-tert-Butylbenzenesulfinimidoyl chloride

N-tert-Butylbenzenesulfinimidoyl chloride 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 N-tert-Butylbenzenesulfinimidoyl chloride rather than just read about it. In short: N-tert-Butylbenzenesulfinimidoyl chloride is a useful oxidant for organic synthesis reactions. It is a good electrophile, and the sulfimide S=N bond can be attacked by nucleophiles, such as alkoxides, enolates, and amide ions.

Key takeaways

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

Reference excerpt

N-tert-Butylbenzenesulfinimidoyl chloride is a useful oxidant for organic synthesis reactions. It is a good electrophile, and the sulfimide S=N bond can be attacked by nucleophiles, such as alkoxides, enolates, and amide ions. The nitrogen atom in the resulting intermediate is basic, and can abstract an α-hydrogen to create a new double bond.

Preparation This reagent can be synthesized quickly and in near-quantitative yield by reacting phenyl thioacetate with tert-butyldichloroamine in hot benzene. After the reaction is complete, the product can be isolated as a yellow, moisture-sensitive solid by vacuum distillation.

Mechanism A nucleophile, such as an alkoxide (1), attacks the S=N bond in 2. The resulting intermediate (3) collapses and ejects chloride ion, which is a good leaving group. The resulting sulfimide has two resonance forms - 4a and 4b. Because of this, the nitrogen is basic, and via a five-membered ring transition state, it can abstract the hydrogen adjacent to the oxygen. This forms a new C=O bond and ejects a neutral sulfenamide (5), giving ketone 6 as the product. N-tert-Butylbenzenesulfinimidoyl chloride reacts with enolates, amides, and primary alkoxides by the same general mechanism.

The Swern oxidation, which converts primary and secondary alcohols to aldehydes and ketones, respectively, also uses a sulfur-containing compound (DMSO) as the oxidant and proceeds by a similar mechanism. In the Swern oxidation, elimination also occurs via a five-membered ring transition state, but the basic species is a sulfur ylide instead of a negatively charged nitrogen. Several other oxidation reactions also make use of DMSO as the oxidant and pass through a similar transition state (see #See also).

Reactions Reacting an aldehyde with a Grignard reagent or organolithium and treating the resulting secondary alkoxide with N-tert-butylbenzenesulfinimidoyl chloride is a convenient one-pot reaction for converting aldehydes to ketones. In some cases, an equivalent of DMPU, a Lewis base, will increase yields. For example, treating benzaldehyde with n-butyllithium and N-tert-butylbenzenesulfinimidoyl chloride in THF gives 1-phenyl-1-pentanone in good yield.

N-tert-butyl benzenesulfinimidoyl chloride oxidizes enolates to enones or enals. N-tert-Butylbenzenesulfinimidoyl chloride can also be used to synthesize imines from amines. Imines synthesized in this fashion have been shown to undergo a one-pot Mannich reaction with 1,3-dicarbonyl compounds, such as malonate esters and 1,3-diketones. In this example, Cbz-protected benzylamine is deprotonated using n-butyllithium, then treated with N-tert-butylbenzenesulfinimidoyl chloride to form the protected imine. Dimethyl malonate acts as the nucleophile and reacts with the imine to give the final product, a Mannich base.

See also Swern oxidation Pfitzner–Moffatt oxidation Corey–Kim oxidation Parikh–Doering oxidation

References

External links N-tert-butylbenzenesulfinimidoyl chloride on Organic Chemistry Portal

Illustrations

Worked examples

Example 1 — a first encounter with N-tert-Butylbenzenesulfinimidoyl chloride

Start with the simplest possible case. Write down what N-tert-Butylbenzenesulfinimidoyl chloride 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 N-tert-Butylbenzenesulfinimidoyl chloride 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 N-tert-Butylbenzenesulfinimidoyl chloride 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 N-tert-Butylbenzenesulfinimidoyl chloride

In research: N-tert-Butylbenzenesulfinimidoyl chloride 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 N-tert-Butylbenzenesulfinimidoyl chloride 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: N-tert-Butylbenzenesulfinimidoyl chloride is common in secondary-school and first-year university syllabi. It links to neighbouring topics Organochlorides, Reagents for organic chemistry, Tert-butyl compounds, so understanding it makes those chapters shorter.
In everyday life: Look for N-tert-Butylbenzenesulfinimidoyl chloride 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 N-tert-Butylbenzenesulfinimidoyl chloride in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what N-tert-Butylbenzenesulfinimidoyl chloride means in your own words.
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Frequently asked questions

What is N-tert-Butylbenzenesulfinimidoyl chloride in simple terms?

Why does N-tert-Butylbenzenesulfinimidoyl chloride 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 N-tert-Butylbenzenesulfinimidoyl chloride?

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 N-tert-Butylbenzenesulfinimidoyl chloride.