Cyclic diboranes(4) based on a chelating monoanionic benzylphosphine linker were prepared through boron-silicon exchange between arylsilanes and B Br . Coordination of Lewis bases to the remaining sp boron atom yielded unsymmetrical sp -sp diboranes, which were reduced with KC to their corresponding trans-diborenes. These compounds were studied with a combination of spectroscopic methods, X-ray diffraction, and DFT calculations. PMe -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.
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