adamantanone
{{Chembox
| ImageFile = 2-adamantanone.svg
| ImageSize = 110 px
| ImageAlt =
| PIN = Adamantan-2-one
| OtherNames = Tricyclo[3.3.1.13,7]decanone
2-Adamantanone
| Section1 = {{Chembox Identifiers
| CASNo = 700-58-3
| PubChem = 64151
| EC_number = 211-847-2
| ChemSpiderID = 57725
| ChEBI = 40611
| ChEMBL = 2041316
| DTXSID = DTXSID9022108
| Gmelin = 122962
| UNII = UI7W503L08
| DrugBank = DB02125
| StdInChI = 1S/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2
| StdInChIKey = IYKFYARMMIESOX-UHFFFAOYSA-N
| SMILES = C1C2CC3CC1CC(C2)C3=O
}}
| Section2 = {{Chembox Properties
| C = 10
| H = 14
| O = 1
| Appearance = white solid
| MeltingPtC = 270
}}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|315|318|410}}
| PPhrases = {{P-phrases|264|270|273|280|301+310|302+352|305+351+338|310|321|330|332+313|362|391|405|501}}
}}
}}
Adamantanone is the ketone of adamantane. A white solid, it is prepared by oxidation of adamantane.{{cite journal |doi=10.15227/orgsyn.053.0008|title=Adamantanone|first1=H. W.|last1=Geluk|first2=V. G.|last2=Keizer|journal=Organic Syntheses|year=1973|volume=53|page=8}} 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.{{cite journal |doi=10.1021/jo100953y|title=Enolates in 3-D: An Experimental and Computational Study of Deprotonated 2-Adamantanone|year=2010|last1=Meyer|first1=Matthew M.|last2=Kass|first2=Steven R.|journal=The Journal of Organic Chemistry|volume=75|issue=12|pages=4274–4279|pmid=20496940}}{{cite journal|last1=Norlander|first1=J.E.|last2=Jindal|first2=S.|last3=Kitko|first3=D.|title=Resistance of Adamantanone to Homoenolization|journal=Journal of the Chemical Society, Chemical Communications|date=1969|issue=19|pages=1136–1137|doi=10.1039/C29690001136}}{{cite journal|last1=Stothers|first1=J.B.|last2=Tan|first2=C.T.|title=Adamantanone: stereochemistry of its homoenolization as shown by 2H nuclear magnetic resonance|journal=Journal of the Chemical Society, Chemical Communications|issue=18|date=1974|pages=378–379|doi=10.1039/C39740000738}}