Surf Wiki
Save to docs
general/organic-reactions

From Surf Wiki (app.surf) — the open knowledge base

Sommelet reaction

Chemical reaction

Summary

Chemical reaction

The Sommelet reaction is an organic reaction in which a benzyl halide is converted to an aldehyde by action of hexamine and water. It is named after the French chemist Marcel Sommelet, who first reported the reaction in 1913.{{cite journal | journal = Compt. Rend. | title = Sur un mode de décomposition des halogénoalcoylates d'hexaméthylène – tétramine | author = Marcel Sommelet | volume = 157 | pages = 852–854

:[[File:Sommelet-Reaktion 1b.svg|The Sommelet reaction]]

One example, thiophene-2-carboxaldehyde is prepared by the reaction of hexamine with 2-chloromethylthiophene. The reaction is formally an oxidation of the carbon.

Reaction mechanism and scope

The benzyl halide 1 reacts with hexamine to a quaternary ammonium salt 3, each time just alkylating one nitrogen atom. Then the benzylammonium undergoes an acid-catalyzed hydrolysis process.

:[[File:Sommelet-Reaktion 2c.svg|400px]]

Depending on the hydrolysis conditions, the hexamine unit might instead break apart, leaving a benzyl amine (the Delépine reaction).

The reaction can also be applied to the oxidation of benzylic amines. In this way, m-xylylenediamine can be converted to isophthalaldehyde.

References

References

  1. {{JerryMarch
  2. (15 March 2011). "The Sommelet Reaction". Organic Reactions.
  3. [[Kenneth B. Wiberg]]. "2-Thiophenealdehyde". Org. Synth..
  4. (1967). "Isophthalaldehyde". Organic Syntheses.
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

organic-reactions name-reactions
Want to explore this topic further?

Ask Mako anything about Sommelet reaction — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report