Adamantanone

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
Names
Other names
Tricyclo[3.3.1.13,7]decanone
2-Adamantanone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.772
EC Number
  • 211-847-2
122962
UNII
Properties
C10H14O
Molar mass 150.221 g·mol−1
Appearance white solid
Melting point 270 °C (518 °F; 543 K)
Hazards
GHS pictograms
GHS Signal word Danger
H301, H315, H318, H400, H410
P264, P270, P273, P280, P301+310, P302+352, P305+351+338, P310, P321, P330, P332+313, P362, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.
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