Highly Efficient Retro-cycloaddition Reaction of Isoxazolino[4,5:1,2][60]- and -[70]fullerenes

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• 作者：Nazario Mart&iacute ; n ; Margarita Altable ; Salvatore Filippone ; Angel Mart&iacute ; n-Domenech ; Roberto Mart&iacute ; nez-Á ; lvarez ; Margarita Suarez ; Marta E. Plonska-Brzezinska ; Olena Lukoyanova ; Lui
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：May 11, 2007
• 年：2007
• 卷：72
• 期：10
• 页码：3840 - 3846
• 全文大小：146K
• 年卷期：v.72,no.10(May 11, 2007)
• ISSN：1520-6904

文摘

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Isoxazolino[4,5:1,2][60]- and -[70]fullerenes undergo an efficient retro-cycloaddition reaction to pristinefullerene by thermal treatment in the presence of an excess of a dienophile and Cu(II) catalysis, whichcan be selectively used in the presence of malonate or pyrrolidine cycloadducts. Trapping experimentsusing N-phenylmaleimide as dipolarophile have shown that the reaction mechanism occurs by thermalremoval of the nitrile oxide 1,3-dipole, in a process which is favored by the presence of Cu(II) as thecatalyst. The ESI-MS study supports the observed retro-cycloaddition process for both C₆₀ and C₇₀derivatives. In contrast to previous electrochemical retro-cycloaddition processes observed in fulleropyrrolidines, isoxazolinofullerenes were stable under oxidative conditions.