Iodo-controlled selective formation of pyrrolidino[60]fullerene and aziridino[60]fullerene from the reaction between C6) and amino acid esters |
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| Authors: | Zhang Xiang Gan Liangbing Huang Shaohua Shi Yaru |
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| Affiliation: | Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China. |
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| Abstract: | The reaction between glycine methyl ester and C60 can be effectively controlled by different iodo-reagents. Addition of DIB ((diacetoxyiodo)benzene) yields the 2,5-bismethoxycarbonyl pyrrolidino[60]fullerene under ultrasonic irradiation; whereas addition of DIB-iodine results in the N-methoxycarbonylmethyl aziridino[60]fullerene under ultrasonic irradiation. The reaction of sarcosine methyl ester with C60 is similar to that of glycine methyl ester under these two conditions. Addition of just iodine to a mixture of sarcosine methyl ester and C60 affords the tetra(amino)[60]fullerene epoxide C60(O)((Me)NCH2COOMe)4. Possible mechanisms are discussed. |
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