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

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 D3-symmetric diastereomer afforded two different ring rearranged ketone-containing produc...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-11, Vol.10 (23), p.5902-5907
Main Authors: Rigoulet, Florian, Artigas, Albert, Ferdi, Nawal, Giorgi, Michel, Coquerel, Yoann
Format: Article
Language:English
Subjects:
Chemical Sciences
Diastereoisomers
Embedding
Iodine
Ketones
Organic chemistry
Oxidation
Oxidizing agents
Polycyclic aromatic hydrocarbons
Rings (mathematics)
Stereochemistry
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Summary: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 D3-symmetric diastereomer afforded two different ring rearranged ketone-containing products embedding a spirofluorene moiety. In contrast, under similar conditions, the C2-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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo01439h