Surf Wiki
Save to docs
general/adamantanes

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

Adamantanone

2-Adamantanone

Adamantanone is the ketone of adamantane. A white solid, it is prepared by oxidation of adamantane. It is a precursor to several adamantane derivatives.{{cite journal |doi=10.15227/orgsyn.060.0113|title=Reductive Coupling of Carbonyls to Alkenes: Adamantylideneadamantane|journal=Organic Syntheses|year=1981|volume=60|page=113|first1=Michael P.|last1=Fleming|first2=John E.|last2=McMurry

Adamantanone and some related polycyclic ketones, are reluctant to form enolates. This barrier arises because the resulting carbanion cannot exist in conjugation with the carbonyl pi-bond.

References

References

  1. (1973). "Adamantanone". Organic Syntheses.
  2. (2010). "Enolates in 3-D: An Experimental and Computational Study of Deprotonated 2-Adamantanone". The Journal of Organic Chemistry.
  3. (1969). "Resistance of Adamantanone to Homoenolization". Journal of the Chemical Society, Chemical Communications.
  4. (1974). "Adamantanone: stereochemistry of its homoenolization as shown by 2H nuclear magnetic resonance". Journal of the Chemical Society, Chemical Communications.
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.

adamantanes ketones
Want to explore this topic further?

Ask Mako anything about Adamantanone — 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