A chameleon oxidant: In Sharpless dihydroxylation of CC bonds osmium tetraoxide is shown to be a chameleon oxidant. Quantum chemical studies show that osmium tetraoxide attacks the CC bond of nucleobases either as an electrophile (blue) or a nucleophile (red) depending upon the nature of the substrate (see scheme; CT=charge transfer).
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Dirk V. Deubel (2003) studied this question.
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