Functionalized Carbon Nanohoops: Synthesis and Structure of a [9]Cycloparaphenylene Bearing Three 5,8-Dimethoxynaphth-1,4-diyl Units

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• 作者：Changfeng Huang ; Yiwei Huang ; Novruz G. Akhmedov ; Brian V. Popp ; Jeffrey L. Petersen ; Kung K. Wang
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：May 16, 2014
• 年：2014
• 卷：16
• 期：10
• 页码：2672-2675
• 全文大小：303K
• 年卷期：v.16,no.10(May 16, 2014)
• ISSN：1523-7052

文摘

A functionalized [9]cycloparaphenylene ([9]CPP) bearing three evenly spaced 5,8-dimethoxynaphth-1,4-diyl units and two macrocyclic [6]CPP precursors have been synthesized. The Diels鈥揂lder reaction between (E,E)-1,4-bis(4-bromophenyl)-1,3-butadiene and 1,4-benzoquinone followed by methylation produces cis-5,8-bis(4-bromophenyl)-5,8-dihydro-1,4-dimethoxynaphthalene as the key intermediate for the construction of the hooplike structures. The nickel-mediated homocoupling reactions followed by aromatization led to the functionalized [9]CPP.