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Extensive Structural Rearrangements upon Reduction of 9 H ‐9‐Borafluorene
Author(s) -
Hübner Alexander,
Bolte Michael,
Lerner HansWolfram,
Wagner Matthias
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405957
Subject(s) - borane , chemistry , boranes , toluene , chrysene , boron , solvent , medicinal chemistry , cluster chemistry , aryl , metal , organic chemistry , alkyl , catalysis , anthracene
Common wisdom has it that organoboranes are readily oxidized. Described herein is that also their reduction can result in remarkable chemistry. Treatment of dimeric 9H‐9‐borafluorene with Li metal in toluene yields two strikingly different classes of compounds. One part of the sample reacts in a way similar to B 2 H 6 , thus affording an aryl(hydro)borane cluster reminiscent of the [B 3 H 8 ] − anion. The other part furnishes a dianionic boron‐doped graphene flake devoid of hydrogen substituents at the boron centers and featuring a central BB bond. A change in the solvent to THF allows an isolation of this dibenzo[g,p]chrysene analogue in good yields.