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/C29695001136.
^ 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/C29695001136.

[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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