Surf Wiki
Save to docs
general/aromatic-ketones

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

Anthrone

Anthrone

Anthrone is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorimetric determination of carbohydrates.

Derivatives of anthrone are used in pharmacy as laxative. They stimulate the motion of the colon and reduce water reabsorption. Some anthrone derivatives can be extracted from a variety of plants, including Rhamnus frangula, Aloe ferox, Rheum officinale, and Cassia senna. Glycosides of anthrone are also found in high amounts in rhubarb leaves, and alongside concentrated amounts of oxalic acid are the reason for the leaves being inedible.

Synthesis and reactions

Anthrone can be prepared from anthraquinone by reduction with tin or copper.

An alternative synthesis involves cyclization of o-benzylbenzoic acid induced with hydrogen fluoride.

Anthrone syntheses

Anthrone condenses with glyoxal to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment.

thumb|center|314px|Tautomeric equilibrium for anthrone. Anthrone is the more stable tautomer relative to the anthrol as has been established also by X-ray crystallography. The tautomeric equilibrium is estimated at 100 in aqueous solution. For the two other isomeric anthrols, the tautomeric equilibrium is reversed: they are phenolic.

Anthrone undergoes nitration using conventional conditions for aromatic nitration, implying that it is the hydroxy tautomer that is the reactant.

References

References

  1. Trevelyan, W. E.. (1952). "Determination of Yeast Carbohydrates with the Anthrone Reagent". Nature.
  2. (2020-01-01). "Chapter 3 - Analysis of polyphenolics". Elsevier.
  3. (1934). "Benzanthrone". Organic Syntheses.
  4. (May 1939). "Inter- and Intramolecular Acylations with Hydrogen Fluoride". Journal of the American Chemical Society.
  5. (2005). "Anthraquinone Dyes and Intermediates".
  6. (2006). "Thermal and Metal-Catalyzed Cyclization of 1-Substituted 3,5-Dien-1-ynes via a [1,7]-Hydrogen Shift: Development of a Tandem Aldol Condensation−Dehydration and Aromatization Catalysis between 3-En-1-yn-5-al Units and Cyclic Ketones". Journal of the American Chemical Society.
  7. (2006). "Tautomeric Equilibria and Pi Electron Delocalization for Some Monohydroxyarenes ''Quantum'' Chemical Studies". The Journal of Organic Chemistry.
  8. Kurt H. Meyer. (1928). "Nitroanthrone". 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.

aromatic-ketones anthracenes
Want to explore this topic further?

Ask Mako anything about Anthrone — 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