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

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–Alder reaction between (E,E)-1,4-bis(4-bromophenyl)-1,3-butadiene and 1,4-benzoquinone followed by methylation produce...

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Bibliographic Details
Published in:Organic letters 2014-05, Vol.16 (10), p.2672-2675
Main Authors: Huang, Changfeng, Huang, Yiwei, Akhmedov, Novruz G, Popp, Brian V, Petersen, Jeffrey L, Wang, Kung K
Format: Article
Language:English
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Summary: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–Alder 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500904x