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 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.