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

文献情報

出版日 2023-10-12

DOI 10.1039/D3QO01439H

インパクトファクター 5.281

著者

Florian Rigoulet, Albert Artigas, Nawal Ferdi, Michel Giorgi, Yoann Coquerel

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要旨

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.

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Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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