Mechanism and number of adducts of photo-addition of glycine methyl-ester to [60] fullerene

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• 作者：Marine de Person ; Adrien Coffre ; Rym Skanji ; Mhamed Ben Messaouda ; Manef Abderraba ; Yongmin Zhang ; Fathi Moussa
• 关键词：Fullerenes ; Photo-addition ; Pyrrolidines ; Azomethine ylide ; HPLC&ndash ; MS ; Dimers
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：19 August, 2013
• 年：2013
• 卷：69
• 期：33
• 页码：6826-6831
• 全文大小：1409 K

文摘

Recently, it has been shown that visible light irradiation of a mixture of C₆₀ and glycine methyl-ester in the presence of oxygen is a direct route to sequentially synthesize higher FP poly-adducts. However, the involved mechanism and the maximum number of pyrrolidine adducts per C₆₀ molecule remained to be ascertained. Using high resolution mass spectrometry and HPLC-MS, we show here that the most probable mechanism involves a first step of azomethine ylide (AMY) formation followed by its [2+3] cyclo-addition to C₆₀, and that the hexakis-adduct is the highest FP poly-adduct (FPPA) obtained under these conditions. Some FPPA and AMY dimers are also identified in the final mixture.