Radical Reactivity of Aza[60]fullerene: Preparation of Monoadducts and Limitations

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• 作者：Georgios C. Vougioukalakis ; Manolis M. Roubelakis ; Michael Orfanopoulos
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：June 18, 2010
• 年：2010
• 卷：75
• 期：12
• 页码：4124-4130
• 全文大小：870K
• 年卷期：v.75,no.12(June 18, 2010)
• ISSN：1520-6904

文摘

Six aza[60]fullerene monoadducts were synthesized by the thermal reaction between the azafullerene radical C₅₉N^• and 9-alkyl-substituted fluorenes, 9,10-dihydroanthracene, or xanthene. Unlike fluorenes, dihydroanthracene, and xanthene, the structurally related substituted diphenylmethanes, ethylbenzene, cumene, 1,2-diphenylethane, 5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene, 10,11-dihydro-5H-dibenzo[a,d]cycloheptene, 9-methylanthracene, and 9-benzylanthracene do not lead to the isolation of azafullerene monoadducts. Moreover, 1,2-dichlorobenzene, the most commonly utilized solvent for azafullerene reactions, reacts slowly with the azafullerenyl radical C₅₉N^• affording the corresponding aza[60]fullerene monoadduct.