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Single functionalization of fenestrindane and centrohexaindane at the molecular periphery

机译:芬斯达丁和中央六氢化茚在分子外围的单官能化

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摘要

The single functionalization of the parent centropolyindane hydrocarbons fenestrindane (2) and centrohexaindane (3) at the molecular arene periphery has been studied. The monoformylation of 2 and 3 using the Rieche method resulted in the corresponding aldehydes, 7 and 10, in 23% and 35% yield, respectively. The -Friedel-Crafts acetylation of 2 furnished 2-acetylfenestrindane (8) in 53% yield, and the Baeyer-Villiger oxidation of 7 followed by hydrolysis resulted in the 2-hydroxy-fenestrindane (9) in 72% yield. The results show that electrophilic attack at one of the eight or, respectively, even 12 equivalent positions of 2 and 3 is a viable method for the monofunctionalization of these polycyclic aromatic hydrocarbons.
机译:研究了在分子芳烃外围的母体中心聚茚满碳氢化合物芬斯达丹(2)和中心六茚满(3)的单官能化。使用Rieche方法对2和3进行单甲酰化,分别得到相应的醛7和10,收率分别为23%和35%。 2的-Friedel-Crafts乙酰化提供53%的产率的2-乙酰基芬太子烷(8),7的Baeyer-Villiger氧化,然后水解,产率为72%的2-羟基-芬那斯丁丹(9)。结果表明,在2和3的八个或什至12个等效位置之一处进行亲电进攻是一种可行的方法,用于这些多环芳烃的单官能化。

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