The reaction of 9-phenyl-9-borafluorene (1) with a diazomethane reagent results in the insertion of a carbene unit into an endocyclic B-C bond to install a carbon bearing a proton adjacent to the tricoordinate boron center (2). With the addition of base, deprotonation occurs to access a 9-borataphenanthrene anion (3). The reactivity of the 9-borataphenanthrene anion with electrophiles, unsaturated organic molecules, and metals will be discussed. Calculations probing the electronic structure will be examined that unravel whether the molecule is best described as a borataalkene or boratabenzene.

Synthesis and reactivity of a 9-borataphenanthrene anion

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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