4.7 Article

Oxidation of a triple carbo[5]helicene with hypervalent iodine

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ORGANIC CHEMISTRY FRONTIERS
Volume -, Issue -, Pages -

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d3qo01439h

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This study demonstrates that stereochemistry is a critical factor in the reactivity of non-planar polycyclic aromatic hydrocarbons.
The reactivities of both diastereomers of hexabenzotriphenylene (HBTP), a triple carbo[5]helicene of the formula C42H24, were examined in the presence of phenyliodine diacetate (PIDA) as an oxidizing agent. The D-3-symmetric diastereomer afforded two different ring rearranged ketone-containing products embedding a spirofluorene moiety. In contrast, under similar conditions, the C-2-symmetric diastereomer afforded predominantly a cyclodehydrogenation product. Altogether, this shows that stereochemistry is a critical factor in the reactivity of non-planar polycyclic aromatic hydrocarbons.

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