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The reaction of naphthalene‐1,8‐diylbis[(trimethylsilyl)methanide] and dimethyl arylboronates afforded the corresponding 2,3‐dihydro‐1H‐naphtho[1,8‐cd]borinine as single diastereomers. Single‐electron oxidation of the boron‐containing heterocycles provided acenaphthylene through the generation boron‐containing cyclic singlet biradicals.
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