Chemical reduction of a hydroxyphenyl-substituted borane triggers a sequential electron- and intramolecular hydrogen-atom-transfer process to afford a hydridoborate phenoxide dianion. On the other hand, hydrogen-atom abstraction of the borane leads to the isolation of a neutral borylated phenoxyl radical, which can be transformed to the corresponding benzoquinone borataalkene derivative by reduction with cobaltocene.
Keywords: boranes; electron transfer; free radicals; hydrogen-atom transfer; reduction.
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