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