Adamantanone Explained

Adamantanone is the ketone of adamantane. A white solid, it is prepared by oxidation of adamantane.[1] It is a precursor to several adamantane derivatives.[2]

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.[3] [4] [5]

References

  1. 10.15227/orgsyn.053.0008. Adamantanone. H. W.. Geluk. V. G.. Keizer. Organic Syntheses. 1973. 53. 8.
  2. 10.15227/orgsyn.060.0113. Reductive Coupling of Carbonyls to Alkenes: Adamantylideneadamantane. Organic Syntheses. 1981. 60. 113. Michael P.. Fleming. John E.. McMurry.
  3. 10.1021/jo100953y. Enolates in 3-D: An Experimental and Computational Study of Deprotonated 2-Adamantanone. 2010. Meyer. Matthew M.. Kass. Steven R.. The Journal of Organic Chemistry. 75. 12. 4274–4279. 20496940.
  4. Norlander. J.E.. Jindal. S.. Kitko. D.. Resistance of Adamantanone to Homoenolization. Journal of the Chemical Society, Chemical Communications. 1969. 19. 1136–1137. 10.1039/C29690001136.
  5. Stothers. J.B.. Tan. C.T.. Adamantanone: stereochemistry of its homoenolization as shown by 2H nuclear magnetic resonance. Journal of the Chemical Society, Chemical Communications. 18. 1974. 378–379. 10.1039/C39740000738.

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Adamantanone".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.