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Cyclic diboranes(4) based on a chelating monoanionic, benzylphosphine linker were prepared by boron-silicon exchange between arylsilanes and B\(_2\)Br\(_4\). Coordination of Lewis bases to the remaining sp\(^2\) boron atom yielded unsymmetrical sp\(^3\)-sp\(^3\) diboranes, which were reduced with KC\(_8\) to their corresponding trans-diborenes. These compounds were studied by a combination of spectroscopic methods, X-ray diffraction and DFT calculations. PMe\(_3\)-stabilized diborene 6 was found to undergo thermal rearrangement to gem- diborene 8. DFT calculations on 8 reveal a polar boron-boron bond, and indicate that the compound is best described as a borylborylene.