Adamantanone is the
ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
of
adamantane
Adamantane is an organic compound with a formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the m ...
. A white solid, it is prepared by oxidation of adamantane. It is a precursor to several adamantane derivatives.
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, 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]
References
Adamantanes
Ketones