高价碘氧化三碳[5]螺旋烯

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2023-10-12 DOI:10.1039/D3QO01439H

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

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引用次数: 0

摘要

立体化学是影响典型三碳[5]螺旋烯六苯并三苯(HBTP)非对映体反应活性的关键因素:d3 -HBTP可以转化为氧化重排产物，但c2 -HBTP不能转化。

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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 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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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.