m‐Benziporphyrin(1.1.0.0) and m‐pyreniporphyrin(1.1.0.0) were prepared as ring‐contracted carbaporphyrins. While m‐Benziporphyrin(1.1.0.0) was unstable, m‐pyreniporphyrin(1.1.0.0) was fairly stable. Both of their PdII complexes showed distorted coordination structures with extremely short Pd−C bonds. As compared with the reported m‐benziporphyrin PdII complexes, these PdII complexes showed considerably small HOMO‐LUMO gaps, despite their smaller molecular size. PdII metalation of the m‐pyreniporphyrin(1.1.0.0) dimer gave the corresponding PdII complex, which showed similar distorted coordination and a smaller HOMO‐LUMO gap. Finally, PdII metalation of a pyrene‐sharing formal p‐benziporphyrin(1.1.1.1) dimer gave a nonaromatic PdII dimer, which rearranged to an aromatic PdII complex upon treatment with alumina.