Adamantanone

Adamantanone
Names
	Preferred IUPAC name Adamantan-2-one
	Other names Tricyclo[3.3.1.13,7]decanone; 2-Adamantanone
Identifiers
CAS Number	700-58-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:40611;
ChEMBL	ChEMBL2041316;
ChemSpider	57725;
DrugBank	DB02125;
ECHA InfoCard	100.010.772
EC Number	211-847-2;
Gmelin Reference	122962
PubChem CID	64151;
UNII	UI7W503L08;
CompTox Dashboard (EPA)	DTXSID9022108;
	InChI InChI=1S/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2 Key: IYKFYARMMIESOX-UHFFFAOYSA-N;
	SMILES C1C2CC3CC1CC(C2)C3=O;
Properties
Chemical formula	C10H14O
Molar mass	150.221 g·mol−1
Appearance	white solid
Melting point	270 °C (518 °F; 543 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H318, H410
Precautionary statements	P264, P270, P273, P280, P301+P310, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, 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 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

^ Geluk, H. W.; Keizer, V. G. (1973). "Adamantanone". Organic Syntheses. 53: 8. doi:10.15227/orgsyn.053.0008.
^ Fleming, Michael P.; McMurry, John E. (1981). "Reductive Coupling of Carbonyls to Alkenes: Adamantylideneadamantane". Organic Syntheses. 60: 113. doi:10.15227/orgsyn.060.0113.
^ 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.
^ 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.
^ 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.

[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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