Single functionalization of fenestrindane and centrohexaindane at the molecular periphery

Linke J, Kuck D (2016)
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES 71(8): 897-904.

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Abstract
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.
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Linke J, Kuck D. Single functionalization of fenestrindane and centrohexaindane at the molecular periphery. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES. 2016;71(8):897-904.
Linke, J., & Kuck, D. (2016). Single functionalization of fenestrindane and centrohexaindane at the molecular periphery. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 71(8), 897-904. doi:10.1515/znb-2016-0067
Linke, J., and Kuck, D. (2016). Single functionalization of fenestrindane and centrohexaindane at the molecular periphery. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES 71, 897-904.
Linke, J., & Kuck, D., 2016. Single functionalization of fenestrindane and centrohexaindane at the molecular periphery. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 71(8), p 897-904.
J. Linke and D. Kuck, “Single functionalization of fenestrindane and centrohexaindane at the molecular periphery”, ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, vol. 71, 2016, pp. 897-904.
Linke, J., Kuck, D.: Single functionalization of fenestrindane and centrohexaindane at the molecular periphery. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES. 71, 897-904 (2016).
Linke, Jens, and Kuck, Dietmar. “Single functionalization of fenestrindane and centrohexaindane at the molecular periphery”. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES 71.8 (2016): 897-904.
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