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Give me five! A new boron-centered radical anion based on the borole framework is an example of a cyclic, planar, and conjugated π system hosting five electrons. Single-crystal X-ray analysis, EPR spectroscopy, and DFT methods indicate that the unpaired spin is delocalized within the borole ring. Despite steric shielding by the mesityl group, the boron atom is still available for radical-type reactions.
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Braunschweig et al. (2012) studied this question.
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