Issue 23, 2023

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

Abstract

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
06 Sep 2023
Accepted
10 Oct 2023
First published
12 Oct 2023
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2023,10, 5902-5907

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

F. Rigoulet, A. Artigas, N. Ferdi, M. Giorgi and Y. Coquerel, Org. Chem. Front., 2023, 10, 5902 DOI: 10.1039/D3QO01439H

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