A concerted transformation is pseudopericyclic if the primary changes in bonding occur within a cyclic array of atoms at one (or more) of which nonbonding and bonding atomic orbitals interchange roles. A formal example is the enol → enol prototropy of pentane-2,4-dione (acetylacetone). Because the π- and σ-atomic orbitals that interchange roles are orthogonal, such a reaction does not proceed through a fully conjugated transition state and is thus not a pericyclic reaction and therefore not governed by the rules that express orbital symmetry restrictions applicable to pericyclic reactions.