6-Aryl-5,6-dihydrodibenzo[][1,2]azaborinines display restricted rotation at the boron-carbon aryl bond, yielding conformational isomers or atropisomers. The stereodynamic processes were monitored by variable-temperature NMR (D-NMR), dynamic enantioselective HPLC (D-HPLC), or kinetic racemization measurements. The absolute configuration of stable atropisomers (compound , Δ = 26.0 kcal·mol) was determined by TD-DFT simulation of the electronic circular dichroism (ECD) spectra. The racemization energy of is more than 12 kcal·mol smaller than its isostere 9-(2-methylnaphthalen-1-yl)phenanthrene.
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