Why is cyclooctatetraene non planar but the cyclooctatetraenide anion planar? I was reading some organometallics and I came upon the preparation of uranocene, $\ce{U(C8H8)2}$. It has two cyclooctatetraenide anions, $\ce{C8H8^2-}$, as ligands, with a uranium atom between them.

It was mentioned that the neutral cyclooctatetraene molecule $\ce{C8H8}$ is non aromatic and has a tub-shaped conformation, but the dianion $\ce{C8H8^2-}$ is planar but aromatic. Why is this so? Can fulfilling Hückel's rule force a cyclic molecule to become planar?
Fulfilling Hückel's rule means that you get to be aromatic.

The reason cyclooctotetraene is non-planar is because its planar arrangement would be antiaromatic. It twists to avoid it, because antiaromatic compounds are unstable with respect to localisation of the π-electrons (see here: What is the justification for H&#252;ckel&#39;s Rule?)

The veritable nanosecond that a molecule has the potential to become aromatic though, it will leap at the opportunity. Any angle strain from being planar is so quickly overtaken by the huge jump in stability that aromaticity brings that the molecule will twist to form an aromatic structure in a blink.